Role overview

The Principal IT Systems Administrator is the most senior individual contributor on the IT Systems team, setting technical direction for core platforms, endpoints, networks, and security within IT Operations. This role drives reliability, scalability, and automation.

You will lead complex initiatives, serve as a top escalation point, and partner across the business to ensure infrastructure and endpoints enable productivity while meeting security and compliance needs.

What you'll do

• System Configuration & Administration: Design and implement complex configurations for core IT platforms (identity, collaboration, infrastructure, SaaS). Establish configuration management, lead performance/reliability improvements, and automate repetitive tasks.
• Workspace & Endpoint Management: Design enterprise-wide endpoint strategies (macOS, Windows, mobile). Develop and enforce security policies, automate software/OS deployments via MDM/EMM, and own compliance reporting.
• Network & Infrastructure: Design and implement complex network configurations (LAN/WAN/Wi-Fi/VPN/voice) for scalability and security. Maintain monitoring, automate network management, and lead infrastructure projects (e.g., migrations, new site buildouts).
• Security Engineering & Operations: Define and drive security strategies within IT Systems (identity, access, endpoints, networks). Integrate security tools (SSO/MFA, EDR, DLP), enforce access policies, and act as a technical lead during critical security incidents.
• Incident Management & Reliability: Define and implement incident response strategies, lead Post-Incident Reviews (PIRs) to drive corrective action, develop runbooks, and oversee on-call rotations.
• Documentation & Knowledge Management: Define documentation standards (architecture, SOPs, runbooks) and ensure knowledge bases are accurate, comprehensive, and easily discoverable.

What you'll bring

• Extensive experience (typically 8+ years) in IT systems engineering/administration, with significant time in senior/lead roles on enterprise-scale environments.
• Deep expertise in: Core IT systems (identity, collaboration, directory), Endpoint management (MDM/EMM, lifecycle), Network infrastructure (switching, routing, VPN), and Security controls (EDR, SSO/MFA).
• Demonstrated ability to design complex configurations, lead large cross-functional projects, and influence architectural decisions.
• Strong automation mindset and proficiency with scripting/infrastructure-as-code (Python, PowerShell, Terraform).
• Proven track record leading major incidents and PIRs.
• Excellent cross-functional collaboration and communication skills, comfortable engaging all levels.
• Experience in environments with security, regulatory, or audit requirements (SOC 2, SOX).
• A bias toward ownership, documentation, and mentorship.

Nice to have: Experience in a high-growth SaaS or technology company, familiarity with CarGurus tools (Okta, Google Workspace/M365, Jamf, Intune), and experience partnering with Security Engineering and GRC.

Role overview

CarGurus is looking for a Product Acceleration Manager to drive quality, speed, and consistency of go-to-market experiences across our dealer product portfolio. You'll work in partnership with product, engineering, sales, design, and marketing to launch impactful dealer products and deliver sustained commercial performance. 

Are you a driven collaborator with a strong track record of delivering exceptional results across the entire product lifecycle? Do you have a deep understanding of the SaaS commercial engine and how technical product features translate into business value and revenue? Are you a systems thinker who can dive deep across a complicated workflow to solve problems and drive continuous improvements? Are you excited by the mission to help millions of shoppers find their next car? Look no further; we'd love to invite you to apply!

What you'll do

• Technical Readiness & Tactical Execution
  • Defining what "readiness" looks like through the lens of product and commercial performance, measuring the efficacy of GTM strategies against adoption and revenue targets.
  • Own the design, measurement, and continuous improvement of dealer product activation for Multiple concurrent product releases simultaneously, prioritizing tasks and resources effectively.
  • Scalable Readiness Strategy: Design a repeatable, high-velocity strategy for product delivery and sales readiness that keeps pace with rapid R&D cycles 
  • Cross-Functional Leadership: Act as a high-judgement general athlete to identify the decisions that matter during each phase of GTM execution and drive to resolution even if that means rolling up your sleeves and unblocking issues yourself
• Strategic Feedback & Insights
  • Field-to-Product Loop: Acting as a strategic conduit for dealer (customer) and sales feedback, synthesizing insights from the frontline (via Gong, Salesforce, JIRA) to help Product refine the commercial viability of new features.
  • Impact Measurement: Measure and implement strategies that minimize activation time (dealer time to value) and hold a high bar for product quality (reduce billing credits due to defective product delivery)
• GTM Process & Strategy
  • Shaping the Commercial Path: Moving beyond the "what" of the product to define the "how" of the GTM approach. You will work cross-functionally with Growth, Sales and Product to operationalize a high volume of product launches and updates into a cohesive execution and narrative.
  • Launch Readiness & Marketability: Partnering with Product Marketing to ensure that technical capabilities are translated into value-based selling resources that Sales can execute immediately.
  • Change Management: Leading the strategy for how we introduce new capabilities to the field, ensuring pre-launch alignment and post-launch reinforcement that drives measurable revenue impact.
  • Workflow Management: Use AI toolkit (Glean, Claude) to streamline GTM communications with a goal of customizing content for specific personas and spending in-person meetings focused on high urgency decisions.

What you'll bring

• Bachelor's degree in Business, Engineering, or a related field.
• 3-5 years of experience in product management, go-to-market strategy, business operations or a similar role, preferably within the technology or automotive industry.
• Proven track record in designing, optimizing, and managing go-to-market and/or operational processes for SaaS businesses
• Proficiency with modern SaaS tools (e.g., JIRA, Salesforce, Gong) and demonstrated curiosity and experimentation with AI workflows (Glean, Claude Code)
• Strong analytical skills with the ability to interpret complex data sets and derive actionable insights 
• Excellent organizational and project management skills, with a proven track record of managing multiple projects simultaneously.
• Exceptional communication and interpersonal skills, with the ability to work effectively in a collaborative environment.
• A proactive and adaptable mindset, with a strong commitment to continuous improvement.

Role overview

CarGurus' Ads Intelligence group is looking for a highly experienced and accomplished Principal Software Engineer to set the technical direction for our platform that will deliver complex market insights through intuitive dealer-facing experiences.

In this high-impact role, you will be the primary technical owner, responsible for setting the multi-year architectural strategy for all market intelligence solutions. You will partner closely with leaders across Product, Data Science, and Product Data Analytics to transform complex competitive data into scalable, insightful, and strategic market intelligence products. If you are an architect focused on solving complex challenges at scale, balancing robust design with long-term stability, we’d love to hear from you!

What you'll do

• Work closely with engineers, product managers, and stakeholders across the company to gather complex product requirements and transform them into effective, robust, and production-ready solutions.
• Define, socialize, and lead the technical vision and architectural roadmap for the entire Ads platform, ensuring long-term performance, reliability, and security across the entire data lifecycle.
• Serve as a technical leader by establishing clear engineering practices, ensuring high standards for code quality, testability, observability, and operational excellence across the team and adjacent groups.
• Guide the technical direction in both our important Java backend services (e.g., microservices, APIs) and sophisticated modern web applications (React) that provide data visualization and intuitive user experiences.
• Mentor, coach, and support the growth of engineers, leading technical design reviews and promoting sound technical decision-making throughout the organization.
• Evaluate, advocate for, and incorporate advanced technologies, including AI/ML capabilities, to enhance the accuracy, breadth, and strategic value of our market intelligence data products.

What you'll bring

• Bachelor’s degree or higher in Computer Science or similar; or equivalent experience in computer science fundamentals including data structures, algorithms, design patterns, and complexity analysis.
• 8+ years of professional software development experience, including 3+ years of experience leading technical strategy or serving as a Principal/Staff Engineer working with Java (or similar languages), and frameworks such as Spring Boot.
• 5+ years of experience designing, building, deploying, scaling, testing, and evolving distributed systems and high-volume transaction applications using service-oriented architecture in 24/7 production environments. Strong proficiency in cloud infrastructure, AWS preferred, including familiarity with infrastructure-as-code concepts (e.g., Terraform).
• 2+ years of experience using cloud infrastructure technologies such as AWS, Terraform or similar cloud services. 
• 3+ years of hands-on experience working with both relational and NoSQL databases, applying the right data models to diverse needs.
• Outstanding written and verbal communication abilities, with a proven talent for articulating complex technical roadmaps and trade-offs to executive leaders, business stakeholders, and engineering teams, ensuring alignment on long-term strategy and execution.
• Experience with full-stack development, especially modern web applications like React, is a strong plus.

Role overview

We're seeking a proactive, independent self-starter to lead project management for our People & Talent organization. This is your opportunity to shape how critical people work gets done—driving clarity, consistency, and flawless execution across a growing organization while partnering directly with leaders on initiatives that impact every employee and our bottom line.

As our Senior Project Manager, you'll own cross-functional programs and projects that span multiple P&T functions and the broader business, reporting to the Senior Director, Compensation & People Operations. You'll oversee much of our program and project portfolio, lead quarterly and annual planning efforts, and ensure crystal-clear ownership, smart prioritization, and on-time delivery of our most important work.

This role demands someone who can communicate effectively with employees at all levels—from individual contributors to executives—to drive our P&T outcomes forward. You'll partner closely with P&T leadership, functional leads, and business stakeholders to execute high-impact initiatives aligned to organizational goals, while enabling consistent delivery through standards, frameworks, coaching, and portfolio-level oversight. Subject matter experts retain accountability for their project outcomes; you provide the strategic backbone that makes it all happen.

What you’ll do

Program & Project Delivery

• Partner with project sponsors and stakeholders to define scope, deliverables, timelines, success metrics, resources, and governance for People & Talent Initiatives.
• Lead cross-functional P&T programs and projects from initiation through delivery, ensuring alignment to quarterly and annual P&T goals. Identify key requirements needed from cross-functional teams and external vendors as appropriate.
• Track and manage interdependencies across teams to ensure predictable delivery and accountability.
• Assist P&T leadership with ad hoc tasks that contribute to our multi-year strategy.

Portfolio, Planning & Capacity Management

• Own P&T program and project portfolio management, including prioritization and alignment with quarterly planning and annual objectives.
• Support quarterly planning efforts by assessing demand, sequencing work, and facilitating trade-off discussions.
• Partner with leaders on P&T capacity planning to balance workloads across planned and unplanned initiatives.
• Support Comp & Audit Committee–related project planning and execution.

Governance, Communication & Change Management

• Establish clear governance models including approval paths, decision tracking, and escalation mechanisms.
• Provide regular, concise updates to leadership on project status, risks, dependencies, and mitigation strategies.
• Partner with stakeholders on change management, communications, and adoption strategies to ensure sustainable outcomes.

PMO Capability & Standards

• Develop and continuously improve project management standards, routines, and frameworks for P&T.
• Build PM capability across the organization through templates, tooling, coaching, and best practices.
• Ensure consistent, transparent reporting across programs and projects.

What you’ll bring

• 8+ years of experience leading medium-to-large, cross-functional programs and projects, including enterprise-wide initiatives; experience within a People & Talent or HR function strongly preferred.
• Proven experience establishing PMO practices, project governance, or portfolio management in a matrixed organization.
• Strong leadership and facilitation skills with the ability to influence without direct authority.
• Experience applying change management principles and measuring adoption and outcomes.
• Comfort partnering with leadership, legal, finance, engineering, and all people & talent teams and navigating complex dependencies.
• Strong analytical judgment and ability to operate effectively in ambiguous, fast-changing environments.
• Demonstrated success defining and tracking KPIs for project performance and portfolio health.
• Bachelor’s degree required; master’s degree preferred in business, engineering, or a related field.
• Strong working knowledge of Agile practices and methodologies.

Role overview

As a member of the Escalation Sales Team, the Escalation Account Executive, L1 will be responsible for negotiating with and re-signing former customers, gathering and analyzing feedback, and collaborating with other members of the account teams to build strategic sales plans for each cancelled account from the SMB account segments. High level objectives are to drive down revenue churn, protect revenue growth per account, and contribute to the overall success of the company's operating plan. This is an individual contributor role with a strong emphasis on sales.

What you'll do

• Engage with former customers to understand their needs, address missed expectations, identify opportunities for re-winning business.
• Lead negotiations to maximize re-won monthly recurring revenue.
• Utilize consultative selling techniques to communicate the value of services and align them with customer needs.
• Accurately forecast monthly re-won revenue and mitigated churn.
• Resolve customer issues or objections in a timely manner, collaborating with internal teams.
• Meet or exceed sales targets by managing a revolving portfolio of accounts and executing a strategic sales plan.
• Maintain accurate records of customer interactions, sales activities, and opportunities.
• Stay informed about industry trends, market conditions, and competitor activities.

What you'll bring

• Excellent organization skills as they pertain to managing different stages of sales process across numerous accounts.
• Experience in a sales-focused role, with a concentration on retention and ROI-based value propositions.
• Able to identify upsell and cross-sell opportunities, both short-term and long-term.
• Strong understanding of CarGurus solutions and related value propositions.
• Excellent communication and interpersonal skills.
• Analytical mindset and ability to make data-driven sales decisions.
• Detail oriented with strong organizational and time management skills.
• Proficiency in using Salesforce and other tools currently within the CarGurus sales stack.
• Self motivated, results driven, and unwavering competitive spirit.
• Adaptability and resilience in a dynamic sales environment.
• Collaborative mindset and ability to work effectively in a cross-functional team.
• Strong sense of accountability and integrity.
• Understanding of how their negotiation strategy and interactions will impact the relationship with CarGurus and potential future revenue.

Role overview

We are looking to hire an organized, highly motivated Project Manager to support the Strategic Program & Project Execution (SPPE) efforts across the organization. This individual will be responsible for leading the execution and delivery of high impact, high visibility projects that are cross-functional in nature. The Project Manager will coordinate across many teams to drive projects that are critical to organizational success and growth. 

This position requires significant stakeholder management, the ability to effectively communicate with management on project status, dependencies, risks and mitigation efforts. Some projects we manage are technical and will require you to learn aspects of the related subject matter. You will play a critical role in establishing best practices to support cross-functional project delivery and will be a key contributor to process improvement implementations in relation to project management capabilities.

What you'll do

• Work closely with project sponsor and cross-functional teams, to plan and develop scope, deliverables, required resources, project plan, budget and timing for cross-functional, enterprise-wide projects.
• Lead and inspire cross functional teams to achieve successful execution of company projects, managing and communicating the vision, purpose and guiding principles as determined by the business leaders.
• Provide regular updates to project teams and business leaders on status, risks and accomplishments.
• Identify key requirements needed from cross-functional teams and external vendors as appropriate.
• Work cross-functionally to track and manage dependencies within projects to ensure on-time delivery.
• Analyze project risks and develop risk mitigation plans to ensure stable execution, while maintaining sight of dependencies and end-state deliverables.
• Ensure stakeholder engagement and approval by establishing a clear approval process, decision tracking and cadenced demos and updates.
• Partner with stakeholders on change management and adoption of improved processes.
• Key contributor to building and enhancing our project management frameworks and best practices to facilitate transparent status tracking and efficient execution.

What you'll bring

• 5+ years of experience managing medium-to-large projects and programs in a project management function.
• Experience in executing enterprise-wide initiatives. Able to define project plans, coordinate resources, manage all project activities, and develop processes associated with program rollout.
• Exceptional leadership, time management, facilitation, and organizational skills.
• Outstanding working knowledge of change management principles and project performance evaluation processes.
• Experience working with engineering and product teams; comfortable working with technical teams.
• Comfortable exercising judgment and using analytical skills in ambiguous situations.
• Preferred qualifications:  
  • Bachelor’s or master’s degree in business or related field.
  • Strong working knowledge of Agile practices and methodologies.
  • Demonstrated experience leveraging agentic tools such as Claude, Gemini, or ChatGPT to streamline work
    processes.

Role overview

CarGurus is looking for a Security Engineer II to add to our growing Threat Detection and Response (TD&R) Team. This is a hands-on technical role that will build our first line of defense against cybersecurity threats in a complex and evolving landscape. You will be responsible for our detection and response lifecycle, identifying and preventing threats from impacting our employees, customers and other stakeholders. As a Security Engineer II, you will have the opportunity to build a platform to identify and stop threats, work with data to solve complex security challenges, and serve as the primary defender for the CarGurus ecosystem.

What you'll do

• Build tools and techniques to detect threats to the company using an engineering-first approach that prioritizes reliability, maintainability and scalability
• Leverage AI and automation to streamline detection and response operations in a safe and reliable manner
• Onboard, normalize and optimize security logging data to support detection engineering, applied ML models, and efficient querying during incidents.
• Develop high-fidelity, rule-based and ML-driven detections as code, utilizing automated testing and CI/CD pipelines for deployment.
• Respond to alerts, threats, and security incidents, including participating in on-call rotations
• Monitor the threat landscape to identify and track emerging threats, ensuring that appropriate detective and preventative controls are deployed
• Partner with development teams to design controls for a cloud first infrastructure (AWS, Kubernetes, etc)

What you'll bring

• 3+ years of experience in software, security, and/or data engineering 
• Strong desire to apply the latest technology including AI and ML to defend against threats
• Experience with data pipelines and data engineering, especially centralized logging, SIEM tools, and data lakes 
• Desire to measure the success of your work with quantitative tools like Precision and Recall
• Experience in at least one programming language like Python, Go or similar
• Experience with cloud infrastructure and technologies like AWS, Kubernetes, containers, IaC, etc
• Experience with good engineering practices like git/GitHub and CI/CD automations 
• Familiarity with tactics, techniques, and procedures used by threat actors
• Familiarity detecting and responding to cybersecurity incidents
• Strong passion for continuous learning, especially relating to cybersecurity and technology
• Team player with strong oral and written communication skills

The Account Manager (AM) role leads the success, retention, and growth of their book of business throughout the customer lifecycle. An AM has a positive relationship with both internal (Account Executives) and external (Dealer Partners) stakeholders. As the primary contact for dealers and dealer groups, AMs are responsible for providing an effective and communicative consultative performance analysis and technical support experience to ensure dealers are getting a positive value from their CarGurus subscription. AMs work closely with Account Executives (AE) to drive growth within the existing customer base through product upgrades, new product sales, and renewals. Through effective relationship management and proactive engagement, the primary objective of an AM is to protect against dealership churn and drive the growth of product and service usage.

What you'll do

• Partner with AE to support the shared book of business
• Become a subject matter authority on all CarGurus products (Listings Packages & Digital Suite)
• Complete post-sale onboarding for new dealerships and dealership personnel
• Be data-driven in quantifying the value of our service to dealers and identifying opportunities for growth and improved results.
• Educate dealers on how to maximize the value of the CarGurus platform by leveraging tools, reports, and best practices
• When appropriate, work with the customer to follow up on technical, billing, and content issues
• Advance cross-departmental collaboration (Support, Billing, Data Integrity, Product, and Engineering) to convey key issues and promote new insights within the CarGurus organization
• Develop deep and wide-ranging relationships with dealership decision makers and staff, growing our span of influence and the number of CG Champions within the dealership

What you’ll bring

• 1–3 years of experience in Account Management, Customer Success, or Client Services, ideally supporting complex or strategic accounts.
• A proven ability to drive retention and growth through strong relationship-building, consultative guidance, and insight-driven engagement.
• Excellent communication skills, with comfort presenting data and recommendations to stakeholders at all levels.
• Strategic problem-solving skills with the ability to analyze data, spot trends, and develop action plans.
• Strong time management and organizational skills to balance a large, dynamic book of business.
• Adaptability and resilience in a fast-moving, evolving business environment.
• Experience working cross-functionally with sales, support, product, and technical teams.
• Proficiency in Google Workspace and/or Microsoft Office; CRM experience (e.g., Salesforce) a plus.

Role overview

As the Technical Product Manager (TPM) for the Pipelines & Automation (PnA) team within Engineering Platform, you will own the CI/CD pipeline platform, software quality tooling, and test automation frameworks that enable all of CarGurus engineering to deliver code faster and with higher confidence.

You will create vision, drive requirements and the roadmap, and support the team by propelling critical initiatives that will fuel our ability to innovate, move quickly, and stay ahead of the competition while embracing and utilizing AI capabilities. That includes our CI modernization (continuing the onboarding of a SaaS CI platform), continued expansion of our Continuous Deployment (CD) pipeline, contract testing, quality gates and frameworks, and the integration of AI-augmented testing and pipeline capabilities.

You will be part of a team of technical product managers who collaborate closely with internal stakeholders to deliver products and systems that directly impact the success of the entire engineering organization.

What you'll do

• Build a strong partnership with the Engineering Platform team — and specifically the Pipelines & Automation squad — to support their service-oriented position within the organization.
• Gain a deep understanding of our CI/CD platform, quality frameworks, pipeline capabilities, and the unique challenges we face as a rapidly growing company.
• Co-own the team's vision and roadmap; generate buy-in and facilitate cross-functional collaboration with a wide range of technical stakeholders across Product Engineering, Data Engineering, Data Science, and other platform teams.
• Complete the CI modernization initiative — design for remaining teams, migration planning, and rollout to engineering teams.
• Champion continued adoption and maturation of our CD pipeline (TTMA), including progressive delivery patterns such as canary analysis and automated rollbacks.
• Own the product direction for quality gates, test automation frameworks, contract testing, and quality metrics collection that are embedded within the pipeline.
• Ensure that prioritization of work aligns with high-level strategies and business objectives.
• Identify opportunities to leverage AI and agentic workflows to improve pipeline reliability, test generation, and developer feedback loops.
• Maintain high levels of engagement with stakeholders through various forms of written and verbal communication, including roadmaps, project plans, status reports, and executive presentations.
• Advocate for adoption of frameworks, tooling, and pipeline capabilities being built out by the centralized platform team.

What you'll bring

• 5+ years of product management experience, including working with engineering teams. Prior engineering background is a plus.
• Familiarity with CI/CD platforms and tooling — experience driving requirements and management of systems such as GitHub Actions, CircleCI, Concourse, Jenkins, or similar. Understanding of pipeline-as-code, declarative pipeline configuration, and progressive delivery patterns (canary, blue-green).
• An understanding of software quality automation best practices, industry standards, and tooling — including quality gates, test automation frameworks, and contract testing.
• Experience gathering requirements from internal engineering customers while filtering into strategic direction.
• Strong judgment to prioritize various incoming and generated requirements based on value-add to the organization.
• A passion for improving the developer experience through reliable, fast, and transparent build and delivery processes.
• An enthusiasm for utilizing AI tools to accelerate your work as well as how AI can enable and accelerate engineering.
• Strong team player with high emotional intelligence and the ability to bring people together across varying personality types and work styles.
• Tenacious self-starter with the ability to work independently, particularly in a highly cross-functional or matrixed environment.
• Excellent written and verbal communication skills.
• The ability to research and propose new tooling to be introduced that will help improve software quality and pipeline reliability.
• The capability to influence quality and delivery transformations by working closely with critical stakeholders.

Role overview

CarGurus is transforming how the company operates by embedding AI into workflows across every function — product, engineering, revenue, finance, support. It’s a software engineering role where the domain is the entire business. You’ll work directly with teams across the org to understand how work actually gets done, identify where AI can change the unit of work or shift where judgment lives, and build the systems that make it real. Some of that is agent-based automation. Some of it is workflow redesign. All of it requires someone who can architect and ship production-quality software, not stitch together SaaS integrations. This is not a Salesforce developer, Boomi connector, or low-code/no-code position, nor is it an enterprise architect or ML model training role.

This is a small, high-autonomy team reporting to the Head of AI Solutions. You’ll have outsized influence on how a publicly traded company with ~$1B in revenue adopts AI — not as a pilot or a demo, but as a structural change in how the business runs. You will be successful here if you are a product-caliber engineer who finds internal workflow transformation genuinely interesting — not a consolation prize, but the most leveraged place to be right now. You’d rather build something real that 200 people use tomorrow than something polished that ships in 6 months.

What you'll do

• Design and build AI-powered workflows and agent-based systems that transform how teams operate across the company.
• Partner directly with stakeholders in revenue, product, engineering, finance, and operations to gather requirements, map existing workflows, and identify high-leverage opportunities for AI.
• Build end-to-end — from scoping and architecture through implementation and deployment. This team ships, it doesn’t hand off specs.
• Work with AI APIs and platforms (Anthropic/Claude, AWS Bedrock, and others) to build agentic systems, automation pipelines, and intelligent tooling.
• Operate across a messy, heterogeneous environment — AWS infrastructure, Salesforce, internal services — without waiting for everything to be clean before you start building.
• Help shape the technical strategy and standards for AI Solutions as a function.

What you'll bring

• 5+ years of relevant software engineering experience.
• Strong software engineering fundamentals — you’ve built and shipped production systems, not just prototypes.
• Proficiency in Python as the primary language for this work; comfort with additional languages is a plus.
• Experience designing APIs, services, and data pipelines. You think in systems, not scripts.
• AWS fluency — you’re comfortable working within AWS infrastructure and services.
• Hands-on experience building with LLM APIs, agent frameworks, or AI-powered applications — not just experimentation, but something that ran in production or was used by real people.
• Ability to operate with high autonomy. You’ll scope your own work, make architectural decisions, and own outcomes.
• Willingness to work across the full stack of a business — including systems like Salesforce that aren’t glamorous but are where the high-impact problems live.

Nice-to-haves:

• Experience with workflow orchestration or automation at scale.
• Familiarity with Salesforce APIs and integration patterns (not Salesforce administration).
• Background in recommendations, search, data science, or ML engineering.
• Experience working cross-functionally with non-technical stakeholders.

Role overview

The Corporate Strategy team is seeking a highly analytical, intellectually rigorous, and self-directed Principal Strategy Analyst to help shape the future direction of CarGurus.

This individual will operate as a senior individual contributor within Corporate Strategy, leading high-impact, enterprise-level strategic initiatives alongside Strategy team leadership and serving as a trusted thought partner to senior leadership. The Principal Strategy Analyst will work across functions to define complex business problems, develop structured recommendations, and translate strategic insights into actionable plans that drive measurable outcomes. This person is expected to be an operator and a strategist; someone that understands the implications of the work they drive at all levels.  

In addition to leading critical initiatives, this role serves as an internal strategy consultant - partnering with business leaders across the company to clarify priorities, evaluate trade-offs, and elevate the quality of strategic decision-making. 

This position reports into the Corporate Strategy function and works closely with executive leadership and cross-functional partners across the organization

What You’ll Do

Strategic Initiatives: Lead high-impact, enterprise-level problem solving

• Scope and lead complex strategic initiatives aligned to company-wide priorities with input from strategy team leadership
• Structure ambiguous business questions into clear hypotheses, analytical frameworks, and execution plans
• Develop rigorous business cases, financial models, and scenario analyses to inform investment and resource allocation decisions
• Synthesize insights into executive-ready materials that clearly articulate recommendations, risks, and trade-offs
• Drive initiatives beyond recommendation — partnering with stakeholders to translate strategy into implementation roadmaps

Thought Partnership & Internal Consulting

• Serve as a trusted thought partner to leaders across the organization
• Act as an internal strategy consultant, supporting business units in evaluating growth opportunities, operational trade-offs, and strategic direction
• Lead structured problem-solving sessions with cross-functional teams to align on priorities and unlock progress
• Pressure-test assumptions, challenge conventional thinking, and improve decision quality through analytical rigor and intellectual honesty
• Provide strategic guidance that balances long-term positioning with near-term execution realities

Competitive & Business Intelligence

• Develop a deep understanding of the automotive and marketplace landscape, including competitive dynamics and emerging trends
• Aggregate and synthesize insights from internal data, market research, and external sources
• Deliver clear, actionable insights that inform company strategy and market-level responses
• Support development of perspectives on new business opportunities, adjacencies, and potential investments

Company Strategy

• Partner with senior leadership to support annual and multi-year strategic planning processes
• Evaluate strategic priorities and ensure alignment between corporate resources and long-term objectives
• Contribute to leadership off-sites and key decision forums with structured analysis and clear recommendations
• Support evaluation of inorganic growth opportunities and major investment decisions as needed

Team Development & Analytical Leadership

• Raise the analytical and problem-solving bar across the Corporate Strategy team
• Mentor junior team members on structured thinking, modeling, and executive communication
• Develop reusable frameworks and best practices that improve team efficiency and impact
• Contribute to a collaborative, high-performance culture grounded in rigor, accountability, and trust

What You’ll Bring

• 5–7+ years of relevant professional experience, including strategy consulting, corporate strategy, investment analysis, or equivalent experience
• Remarkably high bias for action in all aspects of your work with a notably low ego 
• Demonstrated ability to independently lead complex, ambiguous strategic initiatives from framing through recommendation and implementation
• Strong business judgment and structured problem-solving capabilities
• Advanced analytical skills and proficiency in Microsoft Excel and PowerPoint
• Exceptional written and verbal communication skills, with the ability to influence senior stakeholders
• Experience working closely with executive leadership and influencing without direct authority
• Ability to manage multiple high-priority initiatives in a fast-paced, evolving environment

Preferred Qualifications

• Experience in marketplaces, technology, automotive, or related industries
• Exposure to M&A, partnerships, or corporate development
• MBA or equivalent advanced degree

Role overview

Meet CarGurus—the #1 visited online car shopping website in the US. At CarGurus, we’re building the world’s most trusted and transparent automotive marketplace where it’s easy to find great deals from top-rated dealers. 

Founded in 2006 by Langley Steinert (co-founder of TripAdvisor), CarGurus is a technology company with a passion for data and its power to simplify every aspect of the car shopping experience. Using proprietary technology, search algorithms and innovative data analytics, we provide unbiased validation on pricing, dealer reputation and vehicle history.

Are you looking to join the Inventory & Data team at a dynamic and fast-paced technology company? The Director, Inventory Growth will help manage strategy and operations for our Inventory vertical. You will guide key strategic decisions, as well as work cross-functionally to implement critical business initiatives. You'll have the opportunity to work alongside leadership teams in Sales, Marketing, Business Development, Finance, Product, and Engineering. A successful candidate will have strong analytical skills and an ability to work cross-functionally to implement change.

What you'll do

Lead the team that is responsible for growth for the Inventory vertical - including: pricing & packaging, sales enablement, sales strategy and sales analytics. 

Pricing & Packaging

• Define and lead the Inventory vertical pricing strategy, setting clear goals and execution plans to drive transformation and measurable business impact, partnering closely with the GTM Pricing team. Partner closely with Product and Engineering to partner on roadmap pricing implications
• Manage pricing analytics and intelligence for Inventory vertical, delivering actionable insights to sales, finance, and executive leadership
• Cross-functional stakeholder leadership: serve as the primary pricing subject matter expert and trusted advisor to cross-functional partners and the Inventory team on all pricing and packaging initiatives within the inventory vertical

Sales Strategy

• Define and execute the inventory vertical enablement strategy that equips the sales team with the knowledge, tools, and confidence to effectively engage customers partnering closely with GTM Leadership, Product, Marketing, and Operations (inclusive of SMC, PriceVantage and new Inventory solutions)
• Develop and drive the long-term sales strategy and roadmap, aligning with company goals and market opportunities within Inventory vertical. Lead cross-functional initiatives to enhance sales capabilities, integrating people, processes, and tools for scalable growth. Partner with Sales and Marketing Leadership to ensure strategic alignment and execution of revenue-driving initiatives.
• Lead efforts to optimize sales and sales operations processes to achieve superior efficiency, scalability, and performance. Establish sales workflows, leveraging industry benchmarks and innovative practices to enhance operational effectiveness. Drive adoption of optimized processes through change management, training, and continuous improvement initiatives.
• Partner cross-functionally with Product, Product Marketing, and GTM leaders to own the field readiness process for new product launches
• Develop and implement scalable programs that improve sales velocity, rep ramp time, and conversion performance across inventory sales team.
• Lead cross-functional initiatives to support new market entries, sales model evolution, and growth experiments that accelerate reach and impact

Sales Analytics

• Analyze sales funnel data to identify performance gaps and drive initiatives that improve contact-to-close rates, lead follow-up times, and quota attainment.
• Build dashboards, KPIs, and reporting that provide real-time visibility into sales performance
• Insights Delivery: Deliver actionable insights through advanced analytics, including pipeline performance (e.g., conversion rates, deal progression), business hindsighting (e.g., performance driver analysis), and client experience metrics (e.g., NPS drivers and next steps). Build and maintain dashboards and reports to provide Sales Leadership with real-time visibility into performance trends and opportunities. Leverage predictive analytics to anticipate market shifts and inform strategic decisions.

What you'll bring

• 10+ years of relevant experience, including experience in Sales Strategy, Growth, Sales Enablement, Revenue Strategy a plus
• Experienced people leader with a track record of developing and managing high-performing teams.
• Proven ability to influence and align cross-functional leaders in a matrixed environment
• Excellent analytics and communication skills, with experience working cross functionally and with senior stakeholders
• Highly organized, detail-oriented, and capable of managing multiple complex initiatives simultaneously
• Thrives in a fast-paced, evolving environment and can bring structure to ambiguity
• Strong PowerPoint and presentation skills
• Strong organizational skills and attention to detail
• Experience in technology and/or SAAS a plus
• SalesForce experience a plus

Role overview

The Account Executive will focus on growing CarGurus' customer base in the US market by building strong relationships within a book of dealer clients. It will be your responsibility to work with Business Development, Product Specialists, and Account Managers to ensure high levels of product and customer retention. Within this role, you will:

What you'll do 

• Create, preserve, and grow relationships within a designated book of business through prospecting, sales calls, and rapport-building
• Identify and close cross-sell/up-sell opportunities using the CarGurus suite of products
• Grow your book of business through new acquisition opportunities in partnership with Business Development
• Increase revenue per client by re-negotiating subscription rates
• Work with an Account Manager to ensure high customer retention within your book of business
• Work with a Product Specialist to introduce your book of business to and sell CarGurus' newest product offerings
• Accurately forecast monthly sales and retention achievement to management
• Contribute feedback to the larger CarGurus organization by utilizing strong analytical thinking, presentation, and problem-solving skills
• Occasional travel is highly encouraged (1-3x per quarter) to foster long-term partnerships with customers

What you'll bring

• 1-2 years of proven inside sales experience and closing ability
• Strong account management skills
• Good organizational skills
• Strong internal motivation
• Sandler Sales Training is a plus
• The role requires higher levels of collaboration with multiple teams, mostly with the field team

Role overview

CarGurus is looking for a Senior Security Engineer to add to our growing Threat Detection and Response (TD&R) Team. This is a hands-on technical role that will build our first line of defense against cybersecurity threats in a complex and evolving landscape. You will be responsible for our detection and response lifecycle, identifying and preventing threats from impacting our employees, customers and other stakeholders. As a Senior Security Engineer, you will have the opportunity to apply your experience  to provide technical leadership to the team, build a platform to identify and stop threats, work with data to solve complex security challenges, and ultimately defend CarGurus against critical threats.

What you'll do

• Build a platform to detect threats to the company using an engineering-first approach that prioritizes reliability, maintainability and scalability
• Leverage AI and automation to streamline detection and response operations in a safe and reliable manner
• Onboard, normalize and optimize security logging data to support detection engineering, applied ML models, and efficient querying during incidents.
• Apply an engineering mindset to develop high-fidelity, rule-based and ML-driven detections as code, utilizing automated testing and CI/CD pipelines for deployment.
• Own the end-to-end response to alerts, threats, and security incidents, including participating in on-call rotations
• Proactively monitor the threat landscape to identify and track emerging threats, ensuring that appropriate detective and preventative controls are deployed
• Partner with development teams to design controls for a cloud first infrastructure (AWS, Kubernetes, etc)

What you'll bring

• 5+ years of experience in software, security, and/or data engineering
• Strong desire to apply the latest technology including AI and ML to defend against threats
• Experience with data pipelines and data engineering, especially centralized logging, SIEM tools, and data lakes
• Desire to measure the success of your work with quantitative tools like Precision and Recall
• Proficiency in at least one programming language like Python, Go or similar
• Proven experience with cloud infrastructure and technologies like AWS, Kubernetes, containers, IaC, etc
• Proven experience with good engineering practices like git/GitHub and CI/CD automations
• Familiarity with tactics, techniques, and procedures used by threat actors
• Experience detecting and responding to cybersecurity incidents
• Strong passion for continuous learning, especially relating to cybersecurity and technology
• Team player with strong oral and written communication skills
• Effective ability to make decisions independently and provide clear technical guidance to others

Role overview

Join our dynamic team as a US Business Development Representative, where you'll play a pivotal role in acquiring new customers and providing exceptional service to automotive dealerships nationwide. As the first point of contact for many clients, you'll showcase CarGurus' offerings and benefits with professionalism and enthusiasm, utilizing both outbound and inbound strategies.

What you’ll do 

• Initiate contact with potential clients through daily outbound cold calls to both independent and franchise dealerships.
• Qualify inbound leads by engaging in insightful discussions about dealers' business objectives, strategies, and interest in our market-leading products.
• Collaborate with our inside sales team to identify and pursue opportunities for new dealership partnerships.
• Manage and prioritize your time effectively to exceed monthly performance metrics and drive results.
• Travel isn't required for this role. However, as you progress into other sales roles at CarGurus, travel is encouraged to build stronger long-term customer relationships.

What you'll bring

• Bilingual in English/Spanish required 
• A passion for sales and a desire to build a successful career in the sales field. 
• Strong time management and organizational skills to handle multiple tasks and priorities effectively.
• Self-motivation, drive, and a commitment to personal and professional growth.
• Excellent verbal and written communication skills to articulate product offerings and engage with clients
• Coachability and a willingness to learn and adapt in a fast-paced environment.
• Previous sales experience is preferred but not required; we welcome motivated individuals from diverse professional backgrounds.

Please Note: This position marks the starting point for a career in sales at CarGurus. We encourage candidates from various backgrounds who are eager to grow within our sales organization. Successful candidates will show a commitment to personal development through our Business Development Representative (BDR) program, providing pathways for advancement.

Role overview

As a core member of the Data Systems Analysis team, the Associate Business Systems Analyst will support the design, implementation, and ongoing improvement of our data and analytics systems. This role acts as a bridge between business stakeholders and the technical capabilities of our modern data stack, with a growing focus on how we can responsibly apply AI to improve our work. The ideal candidate is eager to learn and explore the new technology in the industry and comfortable working under the guidance of senior analysts and managers to translate business needs into clear, actionable requirements. You will collaborate closely with cross-functional partners across Data, Engineering, and Business teams to document processes, support solution design, and help ensure our systems effectively enable day-to-day operations and strategic decision making.

What you'll do

• Requirements design & analysis: Support requirements gathering sessions with business stakeholders, capturing notes and translating them into clear user stories under the guidance of senior team members. Partner with senior analysts and Technical Product Managers to refine requirements into implementable work items for the engineering team.
• Documentation: Help document current-state and future-state business processes, identifying gaps and pain points. Maintain and update document templates, runbooks, and training materials so that documentation stays current as systems and processes evolve.
• System & data analysis: Assist in analyzing data and system behavior to understand how existing solutions support business processes. Help identify opportunities for process or system improvements, documenting findings and recommendations for review by senior team members.
• Implementation support: Collaborating with engineers, data teams, and product partners to deliver changes that meet documented requirements. Assist with coordination between business stakeholders and technical teams to clarify questions and resolve minor issues.
• AI exploration & enablement: Explore and evaluate AI (ideally build as well) tools and techniques that can improve operational processes, efficiency tracking, and coding workflows for data teams. Prototype small, low-risk AI-assisted workflows and document learnings, limitations, and best practices for the team. Partner with senior analysts and engineers to translate AI opportunities into concrete requirements or proof-of-concept implementations.
• User Acceptance Testing: Help define and document UAT scenarios and test cases based on requirements and business workflows. Coordinate with business stakeholders to schedule UAT, track feedback, and record defects and retest results. 
• Continuous improvement: Support process and documentation clean-up efforts, including template standardization, version control, and knowledge management. Stay up to date on industry concepts and best practices in business analysis and data/analytics and bring relevant ideas back to the team.

What you'll bring

• 1+ year of experience as a Business Analyst, Business Systems Analyst, Data Analyst, or similar role, or relevant internship/project experience.
• A self-starter mindset with strong curiosity and willingness to learn from feedback and mentorship.
• Analytical problem-solving skills and comfort breaking larger problems into smaller, structured questions.
• Ability to navigate ambiguity by asking clarifying questions, documenting assumptions, and escalating risks appropriately.
• Strong written and verbal communication skills, including:
  • Clear meeting notes and action items
  • Well-structured requirements and documentation
  • Ability to explain findings in straightforward business language
• A collaborative working style, with the ability to partner across business, data, and engineering teams and incorporate input from multiple stakeholders.
• Experience or exposure to tools like Snowflake, dbt, and BI platforms
• Experience using related AI tools such as Cursor, Claude, Glean. 
• Strong SQL skills.
• Comfort working in an Agile / scrum environment (e.g., user stories, backlogs, sprints) or a strong desire to learn.
• Business outcome oriented.

Role overview

CarGurus is hiring an IT Service Desk Analyst  to join our IT Team. We are looking for a versatile, analytical, and enthusiastic Engineer who will work closely with business and IT teams in the U.S. and overseas. The ability to be creative and have the initiative to improve processes will be a major part of your success. Your audience will be wildly multifaceted from C level executives, to engineers, to our sales team. One’s ability to collaborate and work efficiently is central to the IT Team’s focus and success. You will be hybrid out of our office on 1001 Boylston Street in Boston, MA. 

What you'll do

• Serve as an escalation point for all complex problems, documenting their solutions in Confluence articles and tickets. 
• Mentor less experienced team members to help them grow. 
• Identify, investigate, and resolve a range of technical issues affecting business systems by exceeding target SLAs (Service Level Agreements). 
• Call out high-impact incidents where appropriate and follow up to ensure resolution. 
• Maintain high customer satisfaction (Internal) for our colleagues. 
• Host ‘walk-in’ sessions in person and online. 
• Drive continuous improvements by implementing perfective measures that provide value and enhance functional performance. 
• Demonstrate flexibility to cope with changing demands based on business priority. 
• Supervise technology trends and make recommendations on incorporating innovative technology into our existing platforms. 
• Develop strong working relationships with key business members, IT project and development teams and relevant 3rd party vendors. 
• Support of system deployments from business and liaising with 3rd party vendors where relevant. 
• Ensure that emerging and ongoing requirements are accommodated by researching and reviewing new systems and applications. 
• Developing tools to automate daily tasks to build efficiencies for the team. 
• Manage user lifecycle processes including onboarding, offboarding, and access control, ensuring compliance with governance policies.
• Other duties as assigned. 

What you'll bring

• 2+ years of desktop support engineering experience or IT-related support. 
• Proficiency in automating workflows and scripting using Python, JavaScript, and others. 
• Experience supporting MACs (OSX) and PCs (Windows and/or Linux) within an enterprise environment. 
• Expert level knowledge of diagnostic utilities and troubleshooting. 
• Experienced working in a team-oriented and collaborative environment. 
• Knowledge of Service Desk operations using Jira Service Management.
• Broad understanding of IT concepts, development practices, and architectures.
• Applied best practice IT Service Management processes in the delivery and support of IT services e.g., the ITIL (Information Technology Instrument Library) best practice framework.
• Strong interpersonal skills, attention to detail and ability to manage tasks simultaneously.
• On-call and occasional hours outside normal business hours according to our needs.
• Exceptional communication skills, able to interface confidently with executive leadership and non-technical users alike.
• Proactive mindset with demonstrated ability to lead projects, improve systems, and influence IT strategy through data-driven insights.
• Relevant certifications (e.g., CompTIA A+/Network+, ITIL Foundation, Jamf Certified Tech/Admin, Microsoft Certified: Modern Desktop Administrator, or equivalent) strongly preferred.
• Provide technical support for AI-driven applications, troubleshooting issues related to APIs, access and data pipelines to ensure optimal performance.
• Monitor AI application performance, analyze logs, and escalate complex issues related to model behavior, latency, and data inconsistencies.

In addition to the responsibilities above, this role also requires regular physical activity, including moving around the office to assist with IT or AV event related tasks, lifting and carrying equipment (upwards of 50lbs), moving tables and chairs, and plugging in devices under desks and other confined spaces. The IT Service Desk Analyst must be able to perform these duties safely and efficiently as part of their responsibilities.

Role overview

CarGurus is looking for a Senior User Experience Designer to lead the evolution of our design system to enable faster, more consistent product development across all products and platforms. Ultimately, you will empower our designers and engineers with a high-leverage single source of truth that multiplies output and streamlines the entire development lifecycle. You are the keeper of shared standards — the person who makes it easier for every designer and engineer to ship better work.

What you'll do

• Define, maintain, and evolve components, patterns, and interaction standards that serve the full product surface.
• Partner closely with Engineering on system implementation, architecture decisions, and handoff processes.
• Proactively identify gaps by monitoring how the system is used across products, and close those gaps before they become workarounds.
• Reduce redundant design and development work by standardizing the most common solutions.
• Support design and engineering teams in adopting the system effectively, through documentation, reviews, and direct collaboration.
• Govern the contribution process: how changes get proposed, reviewed, and approved.
• Maintain a healthy system backlog and triage incoming requests with clear prioritization.

What you'll bring

• 7+ years of experience in UX/product design, with at least 4 years focused on design systems
• Proven expertise working with Figma variables and component architecture, including how they map to coded token structures.
• Working knowledge of front-end fundamentals (HTML, CSS) 
• Experience dealing with accessibility standards (WCAG 2.1 AA) and how they inform component design and documentation.
• Strong systems thinking; you naturally see patterns, spot inconsistencies, and design for reuse.
• Demonstrated experience building and scaling a design system, ideally at a product company with multiple teams.
• Ability to balance consistency with flexibility; you know when to standardize and when to leave room for product judgment.
• Comfort working closely with Engineering, including familiarity with how design tokens, component libraries, and handoff tooling work in practice.
• AI-first mindset by proactively integrating LLMs and automation into the design system workflow to reduce manual friction, while maintaining a critical eye for quality and system integrity
• Clear communicator and cross-team influencer — you can get alignment from designers, engineers, and PMs without authority.
• Detail-oriented and reliable; teams depend on the system being accurate and well-documented.
• Comfortable in a governance role: setting standards, running reviews, and saying no when the system integrity is at stake.

Nice to haves

• Hands-on experience with design token pipelines and tooling (e.g., Style Dictionary, Theo, or equivalent).
• Certification in IAAP/WAAS is a distinct advantage.
• Experience with component library tooling, including writing or reviewing component documentation at the code layer.
• Familiarity with version control (Git) and how design system changes move through a development workflow.
  
  

Role overview

The DevX Tools team is hiring a Software Development Engineer II. The DevX Tools team is part of Engineering Platform's Developer Experience organization. We are responsible for improving the developer experience through tooling, automation, and centralization of critical information needed by developers across the organization. Our tools — including an Internal Developer Portal and an Automated Slack Messaging Systems are used daily by 280+ engineers and are foundational to how CarGurus ships, discovers, and builds software. 

As a Software Development Engineer II (IC2), you will contribute to building and maintaining the internal platforms and tools that empower every product engineering team at CarGurus. You'll work alongside experienced engineers in a collaborative, hybrid environment and grow your skills across the full stack, from backend services and APIs to cloud-native integrations and agentic automations.

What you'll do

• Design, develop, test, deploy, and operate well-architected software systems that improve the developer experience across CarGurus engineering. 
• Build features for Showroom, our internal developer portal that powers deployments, governance, software catalogs, and self-service workflows. 
• Support initiatives such as jobs replatforming, AI-powered code review tooling, agent-driven provisioning workflows, AI-powered AWS infrastructure provisioning and CI/CD pipeline modernization. 
• Facilitate the modernization of an internal developer portal into an AI-first developer platform, introducing AI-powered tooling to streamline workflows, enhancing the developer experience, and supporting large-scale, multi-repository engineering environments.

What you'll bring

• 2+ years of professional software development experience. 
• Strong foundation in Java and familiarity with object-oriented design, algorithms, and data structures.
• Experience building web applications or backend services, ideally with Spring Boot / Spring Framework. 
• A systematic approach to debugging issues within a service or module, including performance impacts. 
• Understanding of the testing pyramid and experience writing automated tests at multiple levels. 
• Familiarity with AWS services, Kubernetes, infrastructure-as-code practices and CI/CD tooling. 
• Exposure to front-end technologies (JavaScript, React, Remix) for building developer-facing UIs is a plus. 
• Interest in AI-powered developer tool and agentic workflows

CarGurus is seeking a Senior DevOps Engineer to join our Cloud Infrastructure team. This team is responsible for providing a reliable, secure, and consumable AWS based platform for revenue-generating applications and the product engineering teams behind them.

In this role you will be a key owner of the cloud platforms that power our global automotive marketplace, and you will help build opinionated, self-service infrastructure that lets engineers ship fast, safely, and with confidence. We are looking for a resourceful, curious individual who is energized by the prospect of designing thoughtful, scalable platforms that are essential to engineers across the entire company.

Role overview

Our team is responsible for designing and operating the core cloud infrastructure at CarGurus. This includes managing domains such as governance, cost attribution, networking, serverless workloads, and OS configuration/orchestration. We also handle CarGurus' edge infrastructure (registrars, DNS, CDN) and maintain essential shared engineering systems like GitHub, Artifactory, and Rundeck, which are critical for how our engineers build, deploy, and operate services.

What you'll do

• Platform Development & Evolution: Design, build, and operate CarGurus' production infrastructure in collaboration with support and build/delivery platform teams. Evolve compute, storage, and data platforms on AWS (e.g., S3, EC2, EKS, ELB, Route53, IAM).
• Automation & Infrastructure-as-Code (IaC): Drive IaC and automation practices (Terraform, Chef, Git, GitHub Actions, Concourse) to ensure secure, repeatable lifecycle operations.
• Cloud Governance: Shape and implement cloud governance, tagging, and reporting standards to support resource attribution and ownership.
• Networking & Edge Operations: Design and operate cloud networking, data protection mechanisms, and edge access components (Fastly CDN, Route53, HAProxy, Datadome).
• Self-Service & Developer Workflow: Utilize, support and enhance self-service platform offerings using AWS, AI and IaC patterns via Terraform. 
• Shared Tools Ownership: Own and improve shared production tools and platforms such as Rundeck, GitHub, and Artifactory.
• Incident Management: Participate in incident response and on-call rotation.
• Mentorship & Documentation: Create and maintain documentation to facilitate the adoption and operation of platform services.
• Innovation: Utilize AI-assisted design and internal tools to explore new architectures, validate trade-offs, and accelerate the design and evolution of platform services and infrastructure.
• Agile Practices: Participate in the team's agile workflow and ceremonies.

What you'll bring

• Cloud Infrastructure & Operations: Deep experience operating production workloads in public/private cloud environments, utilizing role-based security, APIs, and production telemetry (metrics, logs, alerts) to enhance reliability and performance.
• Infrastructure as Code & CI/CD: Extensive background with infrastructure as code, configuration management, and CI/CD pipelines such as Terraform, Chef, Ansible, Puppet, GitHub Actions, or similar.
• Linux/Unix & Programming: Strong, hands-on Linux/Unix experience and proficiency in at least one high-level programming language such as  Python, Ruby, Go or similar.
• Container/Orchestration: Experience with container or VM orchestration platforms such as Kubernetes/Helm/EKS, OpenShift, VMware, or similar.
• Networking & Security: Solid understanding of IP network routing, DNS, load balancing, security, and edge/CDN concepts.
• Web Application Familiarity: Familiarity with large-scale Java web application development and production operations, or similar high-volume environments.

Core Competencies

• Ownership & Communication: Proven ability to manage projects and communicate clearly and effectively with stakeholders.
• Partnership with Stakeholders: Proactive approach to partnering with cross-functional stakeholders to align infrastructure strategy with business goals and drive shared outcomes.
• Problem-Solving: Self-starter mindset with strong curiosity and a hands-on bias for problem-solving. Willingness to take calculated risks to deliver elegant solutions.
• Decision Making: Comfortable navigating ambiguity to uncover root drivers and making practical, well-reasoned design decisions.

Role overview

This role leads execution and optimization of a portfolio of B2B events that drive demand, revenue, and brand perception, and feeds insights and recommendations into the broader event strategy. This person will own end-to-end planning and execution for a portfolio of high-impact events, tradeshows, dinners, swag initiatives, and thought leadership opportunities.

They will work closely with the Sr. Manager of Events, the Director of Brand Marketing, Sales, and cross-functional partners to set goals, define measurement frameworks, and report on performance and insights from our events program.

What you'll do

• Lead end-to-end execution of marketing events, with a primary focus on hospitality events, automotive tradeshows, and VIP customer advisory boards and summits (virtual and in-person). 
• Own event planning and project management, including defining objectives, target audiences, key messages, event formats, timelines, and success metrics.
• Lead Cvent implementation and optimization with cross-functional stakeholders.
• Own relationships with vendors and partners, including procurement, negotiating, and managing contracts, deliverables, and performance.
• Monitor tasks and project assignments, ensuring project schedules are met, risks are surfaced early, and changes are communicated to stakeholders.
• Collaborate cross-functionally with Brand, Sales, Product, Creative, and broader marketing teams to ensure events are aligned to GTM priorities and executed on time and on brand.
• Manage event orders, shipments, and on-site needs, including signage, giveaways, name badges, lanyards, and attendee/participant swag, ensuring a high-quality attendee experience.
• Design and oversee pre-, during-, and post-event communication plans, including invites, reminders, on-site guidance, follow-up, and surveys to maximize registration, attendance, and engagement.
• Facilitate and secure speaking and sponsorship opportunities, partnering with internal stakeholders who own content to shape a compelling on-site presence.
• Own and track annual event and membership budgets for your programs; forecast, reconcile expenses, and maintain accurate records.
• Identify project and program risks and develop contingency plans to ensure successful execution despite changing conditions.
• Support and improve event marketing operations, including processes for survey sends, list pulls, invite sends, registration workflows, and lead handoff.
• Prepare and present event performance reports (e.g., attendance, engagement, lead quality, pipeline impact, ROI) with clear insights and recommendations for optimization.
• Contribute to event best practices and playbooks, helping to evolve how we plan, execute, measure, and scale events over time.

What you'll bring

• 6+ years of B2B marketing event management experience (automotive, technology, or SaaS experience preferred), including high-touch hospitality events or VIP programs.
• Proven track record owning execution for complex, multi-stakeholder events and tradeshows, from brief and planning through on-site presence and post-event analysis.
• Demonstrate strong business and financial acumen, can connect event strategy to revenue, customer health, and broader company strategy with minimal oversight.
• Excellent project management and communication skills, with the ability to manage multiple events and priorities simultaneously.
• Experience influencing and leading cross-functional teams (including senior stakeholders) to drive alignment and successful outcomes.
• Experience managing relationships with external vendors and membership organizations, including negotiation and performance management.
• Experience managing budgets and delivering program events to meet or beat budget expectations.
• Comfort with event performance measurement, including defining KPIs, pulling data, and analyzing results in order to raise insights and recommendations.
• Curious and comfortable experimenting with AI-powered tools to optimize planning, communications, reporting, and other event workflows.
• Familiarity with Google Workspace and event management platforms.
• Experience with Salesforce and hands-on Cvent implementation and optimization is a plus.

Role overview

The Sales Commissions team is looking to hire a motivated Analyst to support the ongoing evolution of the CarGurus commission function. As the Commissions Systems and Data Analyst, you will partner closely with the commission team to support decision-making through data analysis, reporting, and system maintenance.

Reporting to the Director of Sales Incentives, this role will collaborate with the Go-To-Market (GTM) team and cross-functional partners to help ensure accurate and efficient commission processes that align with business goals.

The ideal candidate has a strong analytical mindset, attention to detail, and interest in working with systems and data. This role offers the opportunity to build technical and operational expertise while contributing to key commission processes.

What you'll do

• Support the administration and maintenance of CaptivateIQ, including commission processes and workflows
• Assist in the accurate and timely calculation and distribution of commission payments
• Help identify opportunities to improve processes and data accuracy within commission systems
• Build and maintain reports and dashboards, including performance tracking and plan reporting
• Support commission modeling and reporting deliverables
• Assist with SOX compliance and accrual reporting processes
• Respond to ad hoc reporting requests and support special projects as needed
• Help manage commission-related inquiries and ensure timely resolution
• Provide basic system support and guidance to stakeholders using CaptivateIQ
• Partner with the commission team to support process improvements and operational efficiency
• Support Customer Growth and Retention (CGR) operations in Salesforce, including data validation, updates, and routine audits
• Assist in responding to CGR-related inquiries and help ensure consistent application of policies
  
  

What you'll bring

• Bachelor’s degree in finance, accounting, business administration, or a related field
• 2+ years of relevant experience in finance, sales operations, commissions, or a related area
• Exposure to commission processes or sales incentive programs is a plus
• Experience with tools such as Excel, Google Sheets, and Salesforce; familiarity with CaptivateIQ or similar tools is a plus
• Strong analytical skills and attention to detail
• Ability to manage multiple tasks and prioritize effectively in a fast-paced environment
• Clear written and verbal communication skills
• A proactive mindset with a willingness to learn and take on new challenges
• Ability to work both independently and collaboratively

Role overview

CarGurus is hiring a Product Manager to help shape the future of our Consumer Mobile App, a core growth engine powering how millions of shoppers discover and purchase cars, driving a meaningful share of CarGurus’ marketplace leads.

You will own and evolve some of the most critical product surfaces within our top-rated, rapidly growing iOS and Android apps, driving experimentation, conversion, and product innovation across search, discovery, vehicle details experiences, and more core funnel surfaces. This is a highly visible role with direct impact on customer success and business outcomes, helping millions of shoppers confidently find their next car. Working cross-functionally with Engineering, Design, Analytics, and Marketing, you’ll define product strategy, lead execution, and partner with your squad to ship best-in-class mobile experiences through rapid testing and iteration.

We’re looking for a growth-minded PM who thrives in a fast-paced environment, is deeply customer-obsessed, and excited to turn insights into impactful product experiences.

What you'll do

• Own the roadmap and strategy for key surfaces across the consumer mobile app, acting as the voice of the customer and driving measurable impact on core funnel metrics
• Build alignment and momentum across teams by clearly articulating product vision, strategy, and roadmap
• Translate user needs, behavioral data, and research insights into clear product requirements and intuitive mobile experiences
• Lead end-to-end product development, from ideation and requirements to launch, experimentation, and iteration
• Drive a culture of experimentation by partnering with Product Analytics to develop hypotheses, define success metrics, and run high-quality A/B tests
• Partner closely with Engineering, Design, and cross-functional stakeholders to align on priorities, make tradeoffs, and deliver high-quality products
• Define and track success metrics, analyze performance, and communicate results, insights, and recommendations to stakeholders and leadership

What you'll bring

• 3+ years of product management experience, including 1+ years focused on mobile apps, ideally in consumer-facing, marketplace, e-commerce, or growth-oriented environments
• Proven track record of owning and improving core funnel or conversion experiences, with clear KPI impact on high-traffic consumer products
• Experience in growth or optimization-focused roles, including A/B testing, funnel analysis, and iterative product development
• Strong understanding of mobile platforms, iOS and Android design principles and best practices, react native ecosystem
• Curious and product-minded, with a strong pulse on emerging technologies, mobile apps, and evolving product design patterns
• Highly analytical and data-driven, with the ability to define success metrics, interpret results, and translate insights into product decisions
• Excellent communication and stakeholder management skills, with the ability to align cross-functional teams around strategy, priorities, and outcomes
• Hands-on experience leveraging GenAI to optimize workflows/generate prototypes and agentic coding platforms like Claude Code (preferred)
  
  

Role overview

We are seeking a Senior Manager of Compensation to elevate and scale our compensation programs. This leader will shape and operationalize our compensation strategy, ensuring our philosophy, programs, and practices are competitive, equitable, compliant, and aligned with our business strategy and organizational goals.

The ideal candidate combines deep technical expertise with strategic influence—someone who can guide the business through complex compensation decisions while leading a small team of compensation professionals with enterprise responsibility for base pay, short-term incentives, and equity/long-term incentive programs.

What you'll do

Compensation Strategy & Program Leadership

• Lead the design, strategy, planning, governance, and communication of broad-based and executive compensation programs, including base pay, annual incentives, equity, and long-term incentive plans.
• Refine and advance our compensation philosophy to align with business priorities, market competitiveness, internal equity, and evolving workforce needs.
• Conduct ongoing market research and benchmarking to ensure pay practices remain competitive and aligned with technology sector trends.
• Remain current on compensation best practices and the evolving legal and regulatory landscape; assess risk and proactively recommend solutions to ensure compliance with wage and hour regulations and plan requirements.

Incentive, Equity & Annual Planning Execution

• Oversee equity plan administration, ensuring accurate recordkeeping of vesting schedules, plan compliance, and coordination of settlements in accordance with plan rules and payroll tax requirements.
• Lead the annual merit, bonus, and equity planning cycles, ensuring process excellence, clear communications, and optimized technology workflows that create a seamless experience for leaders and employees.
• Provide support for executive compensation programs and the Compensation Committee, ensuring governance, rigor, and alignment with company objectives.

Advisory Partnership & Governance

• Serve as a trusted advisor to executives, HR Business Partners, and business leaders on company pay structures, pay change recommendations, new hire offers, promotions, and complex compensation matters.
• Provide expert counsel on compensation-related risks and opportunities, translating analytics into actionable business insights.
• Partner cross-functionally with Finance, Legal, Payroll, and People & Talent to ensure compliance, operational rigor, and process excellence.

Communication, Education & Team Leadership

• Develop and execute comprehensive communication strategies that effectively articulate the value of our compensation programs and support talent attraction and retention.
• Build awareness and education initiatives across all levels of the organization to strengthen understanding of total rewards and collective value.
• Inspire and manage a high-performing compensation team, fostering growth, accountability, and continuous improvement.
• Assess team structure and operating model, set priorities, allocate resources, and ensure high-quality execution across all compensation processes.

What you'll bring

• 10+ years of progressive experience in compensation, including 3–5 years in a leadership role.
• Proven success designing, enhancing, and scaling compensation programs within a high-growth or mature technology environment.
• Deep expertise in compensation design, benchmarking, incentive structures, and market analysis.
• Strong knowledge of equity plan administration and regulatory compliance considerations.
• Experience supporting executive compensation and Compensation Committee processes.
• Demonstrated ability to influence senior stakeholders and translate data into strategic recommendations.
• Experience with HRIS and compensation systems; ability to optimize tools to improve workflow and scalability.
• Experience with Sales compensation plans is a plus.
• Bachelor’s degree required; CCP certification preferred.

Role overview

Car shopping is complicated. At CarGurus, we use data and technology to make it simple, giving people the tools they need to confidently find, buy, finance, or sell a car. The best part? Our work makes a real impact. We’re the most-visited car-shopping site in the US and we are growing fast in our international markets. Ready to come along for the ride? 

The Data Engineering team at CarGurus is looking for a Senior Manager of Analytics Engineering to enable data-driven decisions across the company. You will be responsible for delivering scalable and highly performant data models that power reporting solutions for stakeholders in Product Management, Marketing, Finance, and other key areas of the business. We are looking for a candidate who can work collaboratively with our partners and customers, who can also actively contribute to our corporate analytics strategy as we continue to grow and evolve our core business.  

What you'll do

• Lead a team of analytics engineers who will support a diverse set of stakeholders across our business and engineering orgs.
• Provide tactical leadership to your team to build production quality data transformations and maintainable data architectures.  
• Partner on a vision for CarGurus’ business intelligence platform, identifying gaps in our people and technology strategies.
• Build strong partnerships across the company and continuously integrate feedback into the team’s strategy and operations.
• Collaborate with Product Management to prioritize initiatives, manage the execution of projects, and implement agile software development practices as needed.
• Work in conjunction with the Data Governance team to ensure high data quality standards are understood and met.

What you'll bring

• You are an experienced leader with a track record of managing and developing high-performing teams. You excel at coaching, mentoring, and creating growth opportunities for your team members, helping them achieve their professional goals.
• You have a deep understanding of data analytics principles and experience overseeing complex data landscapes, guiding technical direction, and maintaining high standards for data quality and reliability.
• You possess strong communication and collaboration skills, allowing you to work effectively with cross-functional teams, including Product, Analytics, and other Engineering leaders, to drive alignment and achieve business goals.
• You’ve worked with distributed analytics teams.
• 8+ years of experience in product/business analytics, data engineering, analytics engineering, or related field
• 3+ years of hands-on people management experience
• Experience working with a cloud data warehouse (e.g., Snowflake, Databricks, Google BigQuery) and a modern business intelligence platform (e.g., Tableau, Looker, Sigma)
• Expert level SQL proficiency and deep familiarity with dimensional modeling best practices
• Ability to build a multi-sprint plan for a complex data modeling project from loosely defined business requirements 

Role Overview

We are looking for a Senior Manager of Product Marketing to lead product marketing for CarGurus’ consumer products, consumer insights, and differentiated value proposition. You will partner closely with Marketing and Product to deliver insights that shape the product roadmap, bring our products to market, and drive product success. You are deeply knowledgeable about our consumers and able to translate insights into clear strategy and action. The ideal candidate balances big‑picture thinking with strong attention to detail and makes it their mission to ensure we are delighting our consumers. This is a critical management role that reports into the VP of Product Marketing & Insights.

What you'll do

• Own product marketing strategy across the consumer journey (awareness, consideration, decision, purchase, engagement, and retention) for our consumer experience.
• Define and continually refine the overarching consumer value proposition and product positioning, ensuring we clearly articulate what makes CarGurus different and better.
• Partner with Consumer Product to influence the product roadmap with customer, competitive, and performance insights, ensuring we build differentiated products that solve real consumer problems.
• Coach, mentor, and develop a team of Product Marketing Managers, providing clear priorities, feedback, and growth opportunities while fostering a high-bar, low-ego culture.
• Represent the voice of the consumer and develop a deep understanding of our customers and products. Leverage NPS and other customer insights to identify opportunities for improvement and provide input into the product roadmap.
• Build and standardize GTM frameworks and playbooks (tiering, piloting, experimentation, launch, and post‑launch optimization) for new products, features, and experience changes across web and app.
• Synthesize complex data and research into clear narratives that explain the “why” behind recommendations and drive alignment across senior stakeholders.
• Demonstrate a strong command of copywriting and creative judgment, ensuring that all marketing communications are clear, concise, and compelling, while also being customer-centric.
• Partner with our Creative and Performance Marketing teams to drive the performance creative roadmap and brief development, ensuring assets are regularly updated and optimized to drive customer response (e.g., Google, Meta and other ads, emails, landing pages, testimonials, videos).
• Implement project management strategies that align with the organization's overall goals and objectives and manage cross-functional dependencies while supporting project teams through complex problem-solving and decision-making.
• Demonstrate a deep understanding of the strategic priorities and roadmap and the impact your team’s work has, while being proactive and working autonomously, anticipating next steps, stakeholder questions, potential roadblocks, etc., with little day-to-day oversight and clear ownership over initiatives.
• Lead cross-functional working teams across Product, Marketing, Analytics, and Engineering to bring launches and optimizations to market on time, managing dependencies, risks, and trade‑offs.
• Establish clear goals, success metrics, and reporting for consumer product marketing initiatives, ensuring the team’s work is tightly aligned to product, audience, and revenue objectives, and regularly communicate impact and learnings.

What you'll bring

• Bachelor's degree (writing-intensive and/or quantitative major preferred)
• 8+ years of experience, with at least 5+ years in product marketing; experience in consumer / B2C or marketplace businesses strongly preferred.
• 2+ years of people management experience, including directly managing and developing product marketers or adjacent marketing roles.
• Very strong written and verbal communication skills. You are a storyteller with a knack for creating compelling content that will drive results, and can flex between consumer-facing copy, internal narratives, and cross-functional presentations.
• Demonstrated track record leading GTM strategy and execution for consumer products or experiences—from insight and positioning through launch and optimization.
• Deep experience translating customer insights and data into strategy, messaging, and product decisions, including comfort with experimentation and performance metrics.
• Skilled at developing cross-functional relationships and working in close partnership with product and marketing teams
• Ability to thrive in a fast-paced, dynamic environment and manage multiple projects simultaneously and autonomously.

Role overview

CarGurus is looking for a Product Manager, Decision to join our Consumer Product team. The Decision team owns a critical experience on the CarGurus marketplace—helping shoppers decide which car to buy and enabling them to confidently connect with dealers.

In this role, you’ll focus on optimizing the end-to-end journey from listing or paid marketing entry point through lead submission, working closely with stakeholders across Marketing, Brand, Design, Engineering, Analytics, and Attribution. You’ll help evolve existing experiences and build new ones that increase conversion, improve decision confidence, and unlock future growth—while also contributing to broader innovation efforts, including GenAI-powered decision support and new ways for shoppers and dealers to connect.

This role is ideal for a growth-minded product manager who thrives at the intersection of product, marketing, and experimentation, and who enjoys owning highly visible, high-impact surfaces with clear success metrics.

What you'll do

• Own the product vision, strategy, and roadmap for core decision and conversion experiences, including high-intent listing and landing surfaces
• Optimize the shopper journey from acquisition to lead submission, partnering closely with Marketing and Performance teams to improve conversion efficiency and user value
• Lead experimentation and iteration across high-traffic surfaces, using A/B and multivariate testing, behavioral data, and funnel analysis to drive measurable gains in lead volume and quality
• Partner cross-functionally with Engineering, Design, Analytics, Marketing, Brand, and Attribution to launch features that balance shopper trust, brand integrity, and performance outcomes
• Identify and prioritize growth opportunities across surfaces, channels, and entry points, including paid marketing traffic and SEM-driven landings
• Contribute to innovation initiatives on the Decision team, including exploring how GenAI can enhance vehicle understanding, comparison, and shopper-dealer connections
• Act as a strong advocate for the shopper, translating user needs, research, and data insights into clear product requirements and compelling narratives
• Clearly define success metrics, track performance, and communicate results and learnings to stakeholders and leadership

What you'll bring

• 3+ years of product management experience, ideally in consumer-facing, marketplace, e-commerce, or growth-oriented environments
• Demonstrated success owning and improving core funnel or conversion experiences with clear KPIs, ideally on high-traffic consumer surfaces with direct revenue or conversion ownership
• Experience working in a growth or optimization-focused PM role, including experimentation, funnel analysis, and iterative delivery
• Strong cross-functional collaboration skills, with deep experience partnering outside of Product and Engineering, especially with Marketing, Performance Marketing, Brand, or Attribution teams
• Familiarity with marketing technology, performance marketing concepts, or acquisition funnels (e.g., paid search/social, landing pages, attribution, conversion measurement)
• Exposure to GenAI-powered consumer experiences, decision support tools, or personalization systems
• Analytical rigor: comfort defining metrics, digging into data, and using insights to inform prioritization and tradeoff decisions
• Excellent written and verbal communication skills, with the ability to align diverse stakeholders around a shared roadmap and outcomes
• A strong user mindset paired with business acumen—you care deeply about shopper trust and measurable impact
• A bias toward action, curiosity, and continuous learning (plus a sense of humor)

Role overview

The DevX Pipelines & Automation team is hiring a Principal Software Engineer. The team plays a crucial role in enabling faster time-to-market while maintaining high quality. This position involves contributing to the continuous modernization of the platform, with a focus on self-service pipelines and ephemeral environments. The ideal candidate is passionate about Continuous Delivery and platform development, with a strong background in supporting complex software systems and an eagerness to drive efficiency in software delivery processes.

What you'll do

• Develop and enhance CarGurus' Pipeline-as-a-Service utilizing Go and Java.
• Expand the development environment infrastructure to provide ephemeral, hermetic environments.
• Scale the production CI/CD infrastructure to accommodate future demands.
• Manage and enforce governance strategies that promote environmental parity across services and artifacts and ensure high quality.

What you'll bring

• 8+ years of experience as a professional Software Engineer, including 3+ years serving as a technical lead or principal engineer working with Golang, Java or similar languages
• Proficiency with containerization and cloud environments.
• Knowledge in configuration management for distributed systems across multiple environments.
• Outstanding written and verbal communication abilities, with a demonstrated talent for translating technical concepts for both engineering and business audiences.
• Consistent record of being self-motivated, resourceful, and proactive in driving projects and business goals.
• A high-level understanding of Java, Python, or Bash/Unix scripting.
• Familiarity with CI/CD operations, tooling, continuous deployment, and related technologies in a Kubernetes environment.
• An aptitude for leveraging AI tools such as Windsurf, Cursor, or similar to enhance software development and operational efficiency.

Role overview

CarGurus' Dealer Competitive Intelligence group is looking for a highly experienced and accomplished Principal Software Engineer to set the technical direction for our platform that will deliver complex market insights through intuitive dealer-facing experiences.

In this high-impact role, you will be the primary technical owner, responsible for setting the multi-year architectural strategy for all market intelligence solutions. You will partner closely with leaders across Product, Data Science, and Product Data Analytics to transform complex competitive data into scalable, insightful, and strategic market intelligence products. If you are an architect focused on solving complex challenges at scale, balancing robust design with long-term stability, we’d love to hear from you!

What you'll do

• Work closely with engineers, product managers, and stakeholders across the company to gather complex product requirements and transform them into effective, robust, and production-ready solutions.
• Define, socialize, and lead the technical vision and architectural roadmap for the entire Dealer Competitive Intelligence platform, ensuring long-term performance, reliability, and security across the entire data lifecycle.
• Serve as a technical leader by establishing clear engineering practices, ensuring high standards for code quality, testability, observability, and operational excellence across the team and adjacent groups.
• Guide the technical direction in both our important Java backend services (e.g., microservices, APIs) and sophisticated modern web applications (React) that provide data visualization and intuitive user experiences.
• Mentor, coach, and support the growth of engineers, leading technical design reviews and promoting sound technical decision-making throughout the organization.
• Evaluate, advocate for, and incorporate advanced technologies, including AI/ML capabilities, to enhance the accuracy, breadth, and strategic value of our market intelligence data products.

What you'll bring

• Bachelor’s degree or higher in Computer Science or similar; or equivalent experience in computer science fundamentals including data structures, algorithms, design patterns, and complexity analysis.
• 8+ years of professional software development experience, including 3+ years of experience leading technical strategy or serving as a Principal/Staff Engineer working with Java (or similar languages), and frameworks such as Spring Boot.
• 5+ years of experience designing, building, deploying, scaling, testing, and evolving distributed systems and high-volume transaction applications using service-oriented architecture in 24/7 production environments. Strong proficiency in cloud infrastructure, AWS preferred, including familiarity with infrastructure-as-code concepts (e.g., Terraform).
• 2+ years of experience using cloud infrastructure technologies such as AWS, Terraform or similar cloud services. 
• 3+ years of hands-on experience working with both relational and NoSQL databases, applying the right data models to diverse needs.
• Outstanding written and verbal communication abilities, with a proven talent for articulating complex technical roadmaps and trade-offs to executive leaders, business stakeholders, and engineering teams, ensuring alignment on long-term strategy and execution.
• Experience with full-stack development, especially modern web applications like React, is a strong plus.

Role overview

As a core member of the Data Science team, the Principal Data Scientist will lead the design and development of high-impact machine learning systems that power CarGurus’ core products and strategic initiatives.  You will own models and data pipelines end-to-end from problem framing and experimentation through production deployment, monitoring, and continuous improvements. Potential areas of support and ownership include Recommendations, Search Ranking, Instant Market Value algorithms, and new ML-driven product capabilities.

What you'll do

• Own the end‑to‑end design and implementation of production ML models and systems, including model architecture, feature strategy, and evaluation methodology. 
• In partnership with Data and Analytics teams, develop and maintain data pipelines to supply training and inference data for models, using SQL and Snowflake.
• Collaborate with engineering leaders on system and API design to ensure ML solutions meet requirements for latency, reliability, observability, and maintainability in production.
• Apply best practices for experimentation and model evaluation, including offline metrics, A/B testing design, and post‑launch analysis; coach other data scientists in applying these practices rigorously.
• Communicate solutions to stakeholders through written documentation, demos and presentations, and data visualizations tailored to both technical and non‑technical audiences.

What you'll bring

• 7+ years of experience in Data Science or Machine Learning roles, with a consistent track record of shipping, owning, and iteratively improving production ML systems that drive material business impact.
• Deep expertise in Machine Learning techniques for supervised and unsupervised learning across structured and unstructured datasets. Comprehensive knowledge of, and real-world experience with, measurement, evaluation, and testing of models.
• Proven experience deploying and maintaining machine learning services in production, ideally in a cloud environment (e.g. AWS, SageMaker, Snowflake).
• High proficiency in Python (or a similar languages widely used in the data science community) and SQL, plus experience establishing coding, testing, and reproducibility standards (e.g., shared libraries, experiment tracking, templates).
• Ability to communicate technical details, trade‑offs, and analytical findings to audiences ranging from engineers to senior business leaders, using clear narratives and data‑driven recommendations.
• Advanced degree (or proven experience) in Computer Science, Data Science, Mathematics, or any quantitative science which makes use of advanced data analytics or statistical or machine learning techniques

Role overview

The Developer Experience (DevX) Architecture team at CarGurus is looking for an Engineering Manager to lead a team focused on accelerating developer productivity and delivering architectural improvements for CarGurus Engineering.  The results of your work will impact hundreds of engineers across dozens of product teams on a daily basis.

You and your team will take on complex, cross-cutting projects: defining new templates and processes, re-architecting core components, integrating new libraries and frameworks, improving backend performance, and building AI-powered developer tools that give CarGurus engineers a faster and better experience. To succeed in this role, you’ll partner closely with engineers and leaders across many teams, learn and adapt quickly, and translate ambiguous problems into clear, high-impact initiatives. You will own your projects end-to-end, lead a team of talented engineers, and collaborate with fellow engineering managers and product partners to solve interesting problems with broad scope.

What you’ll do

• Lead and grow a high-performing DevX engineering team, providing coaching, feedback, and clear expectations.
• Set and communicate architectural direction for developer experience, in partnership with Staff/Principal engineers and other platform teams. 
• Own a roadmap of technical investments: propose ideas, shape scope, provide estimates, measure, and sequence work to maximize impact on engineering effectiveness. 
• Partner across the organization with engineers, managers, and product to deeply understand their pain points and design pragmatic solutions that scale. 
• Drive predictable delivery by breaking down ambiguous problems into small, testable increments and releasing value iteratively. 
• Lead the full software development lifecycle for your team’s services and tools: design, implementation, testing, deployment, monitoring, and continuous improvement, with a strong emphasis on clean, well-tested, and efficient code. 
• Identify high leverage/ROI opportunities for AI-assisted development (code assistants, test generation, internal agents), partner with security and compliance to define guardrails, and integrate these capabilities into our SDLC
• Use technologies like Java, Spring Boot, AWS, Kubernetes, and AI-assisted development tools to improve our core architecture and platforms. 
• Advance and champion engineering best practices (reliability, observability, performance, and security) and help teams adopt them through patterns, templates, and guidance. 
• Strategically invest in critical platform areas, such as authentication and other shared services, to reduce risk and unlock faster delivery for product teams. 

What you’ll bring

• 5+ years of hands-on software design and development experience building and operating production systems. 
• 3+ years in an Engineering Manager or equivalent technical leadership role, leading teams that ship software in production. 
• Experience building and operating large-scale, performant web applications, and familiarity with modern technologies and patterns that enable them (distributed systems, microservices, cloud-native architectures, observability, etc.). 
• Hands-on experience with modern strongly typed backend languages (Java, C#, etc) and cloud platforms (AWS, GCP, etc)
• Hands-on experience with modern AI tools (e.g., code assistants, test generation, or internal agents) and a perspective on how to responsibly apply them to improve developer experience.
• Strong project management and collaboration skills, including experience working across multiple teams and stakeholders in an iterative, agile environment.
• A people-focused technical leader with high emotional intelligence, who can motivate, coach, and develop engineers at different levels. 
• A clear, adaptable communicator who can tailor your message for audiences ranging from junior engineers to senior business leaders and third-party vendors. 
• A curious, growth-oriented mindset—you enjoy learning new domains, experimenting with new tools, and continually expanding your capabilities. 
• Bachelor’s degree in Computer Science or equivalent practical experience.

Role overview

CarGurus’ Front End Platforms team is hiring an Engineering Manager. The Front End Platform team plays a key role for CarGurus to operate at scale and improve developer efficiency. We are constantly modernizing our technology platform and are looking to define key architectural capabilities, and guide development teams on their successful implementation. The team’s mission is to enable teams to build performant and scalable UIs and lead best practices for Front End Engineering.

What you’ll do

• You’ll manage a team of talented engineers while providing technical leadership and mentorship to the broader team.  Your team is primarily responsible for maintaining our design system and our microservice template for building isomorphic Remix and React applications. 
• Your team’s mission is to enable engineering teams to build highly-performant, scalable, excellent products through advocating for architectural standards and providing common UI libraries and tooling.
• This is a highly visible role that requires you to facilitate and collaborate on multiple cross-team projects at the same time. You will use your leadership expertise to drive groups with disparate interests to decisions, seeing those through to impact. You will make pragmatic decisions, balancing strategic and tactical needs. You will help senior leadership manage risk and make sure we are making the right trade-off decisions.
• Coach your team to accurately estimate and prioritize units of work and drive the incremental release of moderate to large sized projects.  
• Partner with your product manager to define the team’s roadmap.
• Contribute to high level architectural discussions and decisions across multiple areas and teams. 
• Be deeply engaged in the full development lifecycle designing, developing, testing, deploying, maintaining, monitoring, and improving software
• Advocate for new technology and new methodologies
• Have fun as you continuously learn and expand your and your team’s capabilities

What you’ll bring

• Expertise with JavaScript and/or TypeScript, NodeJS Frameworks and libraries, and React
• Direct experience with Remix or Next is a huge advantage.
• Highly proficient with HTML and CSS
• Excellent communicator who can tailor messaging based on audience, which can range from junior engineers to senior business leaders to third-party vendors
• People-focused technical leader with 2+ years of experience
• 5+ years of product software development experience at scale
• Provides constructive and timely performance evaluations
• Strong project management skills, experience with Agile methodologies
• Excellent collaborator with proven experience working in a cross-functional team including Product, Design, Analytics, Marketing
• Detail oriented leader who makes data-driven decisions

Role overview

Our Information Security team is responsible for ensuring the security of our customers and the safety of our data. As the Manager of Security GRC, you will guide the evolution of our established GRC function. You aren't just maintaining a program; you are maturing our capabilities to ensure that security is a tailwind for our business, transforming complex regulatory requirements into a competitive advantage.

You will be a strategic leader who balances high-standard execution with a focus on Revenue Enablement, ensuring our security posture removes friction from the enterprise sales cycle and reinforces our market position as a trusted partner.

What you'll do

• Take ownership of an established team to elevate our GRC maturity. You will develop and refine our Integrated Management System (IMS) across ISO 27001, 27017, 27018, and SOC 2 Type II.

• Modernize our risk reporting by leveraging quantitative risk management. You will move beyond qualitative "Red/Yellow/Green" charts to provide real-time, data-driven insights and financial risk projections using FAIR principles.

• Serve as a leading voice on our AI Governance Committee. You will guide the secure adoption of AI/LLM features within our product and oversee the governance of AI integration across our internal SaaS ecosystem, aligned with ISO 42001.

• Focus on GRC as a revenue driver. By maturing our compliance and risk functions, you will ensure our security trust posture supports global growth and instills immediate confidence in our largest enterprise customers.

• Partner with Product and Engineering to validate and mature technical controls within cloud environments (e.g. AWS, GCP) and cloud data warehousing environments (e.g. Snowflake). You will ensure that compliance is a seamless part of the CI/CD pipeline and agile software development lifecycle.

• Provide expert guidance on GDPR and CPRA, ensuring our risk management strategies remain resilient in a rapidly changing global privacy landscape.

What you'll bring

• You have 7+ years in Information Security and a track record of maturing established teams. You know how to keep team performance on track while maintaining momentum toward strategic goals.

• You have a deep understanding of AWS security services and Snowflake data governance. You are comfortable challenging and supporting technical teams to innovate and solve strategic challenges.

• You embody a growth mindset and use data and facts to inform priorities. Experience with SAFE Security or similar CRQM platforms is a significant plus.

• A Change Leader: You are comfortable with ambiguity and adapt quickly when priorities change. You encourage experimentation within your team to automate evidence collection and risk discovery.

• A Caring Collaborator: You lead with empathy and inclusion, building diverse teams that support one another. You are a cultural ambassador who can see things from others' viewpoints and reconcile multiple stakeholder views to drive results.

• A Clear Communicator: You bring people along with your vision. You can translate technical risk into business value for executive decision-makers and functional leaders.

Our Leadership Competencies:

We hire leaders who are a Catalyst for Impact, a Coach to their peers, a clear Communicator, an innovative Change Leader, and a Caring Collaborator. In this role, you will be expected to:

• Set high standards and take full ownership of the GRC roadmap.

• Proactively manage the growth of team members through clear feedback and experiential opportunities.

• Engage key decision-makers across business functions to support complex, cross-functional initiatives.

• Navigate organizational dynamics to establish accountability and ensure successful delivery of results.

Role overview

The Manager, Data Science will lead an Inventory & Dealer Data Science team focused on developing, deploying, and optimizing machine learning models that power CarGurus’ products and business insights. Sitting within the broader Data Science organization, this team is responsible for modeling automotive marketplace dynamics and dealer behavior. The team owns Machine Learning solutions end-to-end across the ML lifecycle, from R&D to production. This leader is accountable for the team’s strategic direction and impactful delivery, while building a culture of innovation, technical excellence, and collaboration. The Manager partners with Product, Engineering, Analytics, and cross-functional stakeholders to ensure team efforts advance CarGurus’ goals in intelligence-powered products.

What you'll do

• Oversee the development, training, and evaluation of machine learning models covering Inventory and Dealer intelligence. Leverage modeling techniques including recommendations, demand forecasting, churn risk prediction, and valuation algorithms.
• Facilitate experimentation, A/B testing, and measurement of production models, ensuring robust evaluation of business impact
• Build and develop a high-performing team - providing regular coaching, feedback, and performance assessments; ensure equitable access to growth opportunities.
• Drive innovation, continuous improvement, and adoption of best-in-class ML and AI practices. Champion best practices across the organization.
• Participate in roadmap planning, aligning the team’s work with broader business priorities and long-term strategy. Flag resource constraints and escalate tradeoff decisions when needed.
• Act as a visible, accessible leader - communicating objectives, updates, risks, and wins to all stakeholders.
• Partner with peers in the Machine Learning Platform, Product and Data teams, and other stakeholders to facilitate effective cross-team working relationships and represent data science in cross-functional forums.

What you'll bring

• 5+ years of experience in a data science or machine learning engineering role
• 2+ years of people leadership experience
• Deep expertise in machine learning models and their application to classification, regression, ranking, and recommendation problems. Familiarity with standard evaluation metrics and statistical best practices.
• Experience deploying and owning models in production and a working understanding of MLOps practices.
• Strong working knowledge of Python development best practices and the Python ML ecosystem (e.g., scikit-learn, PyTorch, XGBoost, numpy, pandas).
• Experience with cloud platforms, particularly AWS, including deploying, monitoring, and troubleshooting ML models.
• Effective communication and facilitation abilities with both technical and non-technical stakeholders (including data scientists, product management, senior leadership, and engineers).
• Experience contributing to the technical direction for a team and a strategic mindset for prioritizing projects and aligning them with business goals.
• Knowledge of standard software development methodologies and a history of driving continuous improvement.
• Experience in a collaborative, cross-functional environment, with the ability to build effective working relationships and foster an inclusive team culture.

Role overview

We’re looking for an analytical, strategic-thinker, result-oriented leader with experience in search and AI engine optimization (SEO/AIO) to join our team at CarGurus and drive our innovation in AI organic traffic. Within the Performance Marketing team, this individual will be responsible for growing CarGurus organic traffic and conversions, focused on AI search and AI/social engines, building a best-in-class organic program and cementing CarGurus as a top organic result for automotive search in the US and our International markets, Canada and the UK. This role will proactively research, analyze and communicate emerging trends in new AI channels, drive the strategy and aggressive testing plans, and execute, measure and optimize SEO/organic initiatives to ensure we are on the leading edge, in partnership with a team of SEO specialists, engineers, Editorial, Product, Marketing & Analytics teams. 

What you'll do

• Executive Communication & Strategic Alignment: Proactively communicate AI search and emerging SEO trends, key implications for CarGurus and suggested strategic priorities to senior executives and board-level audiences. This includes crafting compelling narratives supported by data, anticipating objections, and driving alignment around recommendations. 

• Leadership & Results Driven Innovation: Balance strategic risk-taking and the practical implementation of new ideas to drive SEO/AIO conversions growth and industry leadership. Demonstrate a willingness to allocate resources toward testing innovative high-potential tactics—like AI-driven content clusters or unconventional site architectures—while driving a framework for measurable results.

• Strategy Development: Define and size opportunities, strategic priorities, and roadmap to drive organic AI/social growth based on emerging trends, current performance and data insights; includes informing the Editorial Content team’s roadmap and prioritization. 

• Execution: Oversee execution and optimization of performance-oriented campaigns & initiatives across search AI (e.g. Google AI overviews), emerging AI engines (e.g. Chat-GPT) and social platforms (e.g. Reddit, X, Meta, YouTube) to drive organic visits and conversions.  

• Conversion Optimization: Continuously optimize landing page conversion rates at various stages of the customer journey, from content/research to conversion-oriented pages.

• Testing and Measurement: Analyze marketing data and metrics to measure the effectiveness of SEO efforts, including A/B testing, report building and analysis, and communicate the results and data-driven decisions to key stakeholders.

• Reporting & Forecasting: Monitor SEO/AI performance across all CarGurus markets, reporting regularly to the Executive Team on synthesized trends, work and impact. 

• Resource Management: Define and manage budget and engineering resource allocation. 

• Cross-functional Collaboration: Lead internal communications and collaborate with other departments, such as Engineering, Product, Editorial Content, Analytics and Other Marketing teams to align efforts with overall business goals and ensure adequate prioritization. 

• Market Research: Stay updated on industry trends, competitor strategies, and customer preferences to inform SEO initiatives and strategy.

What you'll bring

• SEO/AI Knowledge: 8+ years of professional experience in SEO, preferably in-house and enterprise-level, with a strong understanding of SEO principles, strategies, and recent AI trends. 

• Strategic Thinking: Strong critical thinking and problem solving skills to identify opportunities and priorities with strategic context and understanding.

• Communication Skills: Strong ability to concisely synthesize and communicate key insights, results and recommendations to key partners and senior leadership, in verbal presentations and written communications.

• Data Analytics: Passion for data, and testing new features or improvements. Proficiency in using data analytics tools (Looker, Google Analytics) and SEO tracking platforms to analyze performance and make data-driven decisions. 

• Adaptability: Ability to work in a fast-paced environment,  learn and adapt to changing marketing trends and technologies, and adapting priorities to critical business needs.

• Cross-Functional Collaboration: Ability to effectively liaison with internal teams, subsidiary partners, and executive team regarding SEO initiatives and progress.

• Team Management: Experience leading teams, particularly content and/or engineering teams

• Attention to Detail: Precision in tracking data and ensuring roadmap elements are executed correctly.

Role overview

CarGurus is looking for a Senior Product Data Analyst to navigate our rich data environment and drive impactful outcomes for our customers and business. You will work cross-functionally to build out core data assets, empower go-to-market teams with revenue-generating insights, and design novel metrics to guide the business.

Our Product Data Analytics org supports our Product, Engineering, and Go-to-Market teams, providing the final word on all analytics for CarGurus’ user and dealer experiences. We are looking for thoughtful, curious, internally driven analytics experts who don’t just pull data, but draw the “so-what” from complex, disparate sources and present these findings to internal teams and external customers. 

What you’ll do

• Communicate and present complex quantitative findings in easily digestible terms to company leadership, homing in on key takeaways. Concretely and informatively respond to any probing, on-the-spot follow-up questions from senior decision-makers. 
• Conduct exploratory empirical analyses using SQL and Python that bridge disparate data sources (e.g. website usage, subscription records, inventory volumes, etc.). to quantify product performance, user behavior, and/or market trends. Distill unstructured “big data” around product performance, user behavior and/or market insights into actionable outcomes .  
• Architect new data assets and production-grade data marts via dbt. You will fix modeling bottlenecks and optimize data lineages to ensure scalability. 
• Serve as the technical expert in high-stakes Go-To-Market engagements. You will partner with Sales and Customer Success teams to provide data-backed proof of value, participating in client-facing meetings to help secure new partnerships or mitigate churn through sophisticated impact analysis.
• Partner with engineering teams to advance the company’s core data modeling and architecture, with a focus on optimizing, integrating, and distilling large raw datasets and metadata. 
• Creatively compress sweeping, high-level exploratory requests into specific calculations that address your stakeholders’ underlying needs. Relentlessly dig into the data, taking initiative to consult with other individuals and teams as you judge necessary. Go beyond the letter of the initial assignment, to hammer out any anomalies or self-direct your inquiry into other relevant issues. 
• Use Claude Code and agentic workflows to automate,  to automate, accelerate, and escalate the sophistication of your analyses.
• Advocate for specific, data-driven product innovations that help further company strategy, primarily in partnership with the Product, Engineering, and Go-to-Market teams. 
• Lead rigorous, holistic discussions about statistical analyses and ML modeling.  You are expected to be a “self-teaching” practitioner, staying ahead of quantitative trends. 
• Participate in brainstorming and planning discussions across the organization to these ends. Avoid passivity in the face of flawed proposals; tactfully and persuasively push back against potential missteps.
• Craft the metrics that define success. You’ll condense abstract or loosely-defined concepts into concrete calculations and relentlessly audit existing metrics for accuracy and relevance.
• Build intuitive dashboards and other visual monitoring tools to guide stakeholders’ daily decision-making. Experiment with new kinds of visualizations that you believe could be better utilized in the organization. Re-work underlying code to appropriately structure visualization inputs.

What you’ll bring

• 4+ years of experience in analytics, with a proven track record of influencing business strategy through complex modeling and applied statistics. 
• Expert-level skills in SQL, Python, and dbt. Proficiency with file manipulation and version control via Git.
• Strong data storytelling and communication skills, presenting findings to senior leadership and external customers.
• Hands-on experience leveraging  GenAI  to optimize workflows and agentic coding platforms like Claude Code (preferred) or Cursor.
• A self-starter who can take a “grassroots” idea, scope its viability, and bring it to scale.
• A natural thought leader with a proven track record of influencing business strategy.
• Strong command of hypothesis testing, parametric/nonparametric regression, and building automated statistical pipelines. 
• Knack for creative data visualizations.
• You are a “tactful challenger”. You don’t just accept flawed proposals; you provide data-backed alternatives and can explain p-values to executives as easily as you explain them to technical audiences. 
• Strong project planning skills, with experience building roadmaps, estimating required resources, and flagging interdependencies with other teams.
• Preferred tools/programs: Snowflake, Claude Code, Cursor, Looker/LookML, Omni.

Role overview

CarGurus is seeking a Senior Product Manager, Dealer Engagement Platform (DEP) to lead the transformation of our next-generation dealer-facing platform into a fast, modern, and thoughtfully designed experience. The DEP serves as the foundation for how dealers interact with our ecosystem, powering engagement, insights, and growth across our suite of tools.

This role will shape the user-facing architecture and experience that unifies dealer workflows across CarGurus. You’ll drive a vision for a platform that’s not only scalable and extensible but also delightful, performant, and easy to iterate on — enabling rapid product innovation and cohesive dealer experiences.

As the product owner for the DEP, you’ll collaborate closely with Engineering, UX, Product Analytics, and cross-functional product teams to define a platform that brings consistency, flexibility, and speed to every dealer interaction.

What you'll do

• Own the vision and roadmap for the Dealer Engagement Platform, driving a fast, intuitive, and modern experience built on strong usability and performance principles.
• Evolve the DEP’s design system and component architecture to enable rapid iteration, visual consistency, and seamless reuse across dealer-facing products.
• Collaborate with UX and Engineering to ensure the platform reflects best-in-class layout, interaction, and responsive design practices.
• Partner with dealer product teams to identify shared needs and accelerate delivery through scalable, reusable front-end components and unified workflows.
• Balance quick usability improvements with long-term platform scalability and technical excellence, ensuring a foundation that supports continuous innovation.
• Champion a cohesive visual and interaction language across all dealer experiences, ensuring every touchpoint feels unified, modern, and easy to use.

What you'll bring

• 5-7+ years of product management experience, including ownership of front-end platforms, design systems, or user-facing product foundations.
• Proven success in building modern, performant, and extensible front-end architectures that enable fast iteration and consistent user experiences.
• Strong understanding of user management, roles and permissions, and how these underpin cohesive multi-product ecosystems.
• Deep collaboration experience with UX and Engineering to deliver scalable, reusable components and intuitive design patterns.
• Ability to translate technical and design decisions into business impact, driving alignment across technical and non-technical stakeholders.
• Strategic, systems-level thinking with a bias for action—balancing immediate usability wins with long-term platform evolution.
• Excellent communication, storytelling, and stakeholder management skills within a matrixed, cross-functional environment.
• Familiarity with marketplace or B2B SaaS platforms; automotive or retail industry experience is a plus.

Role overview

The Director of Sales, Inventory Management, will be instrumental in helping CarGurus establish a strong presence in the substantial and rapidly expanding Inventory Management segment of the automotive industry. This individual will serve as an effective coach, leading a team focused on increasing revenue with existing customers by driving the adoption of our new product, PriceVantage. The Director will define and execute the strategy for this department, encompassing all aspects related to our current and future products within the inventory management sector. We seek a candidate with experience in a high-velocity sales environment, characterized by short sales cycles and ambitious goals for intelligent expansion. This represents an excellent opportunity for a highly driven leader to refine an already successful sales team into a more sophisticated and polished operation. 

What you'll do

• Manage a growing team of sales representatives and managers
• Work cross-functionally with other sales teams and departments
• Be vocal ‘voice of the dealer’ and communicate the needs of our customers and product requirements
• Manage through metrics: both for reporting business results and directing coaching and training efforts
• Work with teams via both direct impact and influence
• Drive the creation of the strategic annual sales plan
• Implement optimal organization, process, and tactics to maximize close rates and revenue from each salespersons and sales teams book of business
• Effectively communicate, formally and informally, up and down the organization
• Effectively and efficiently handle all aspects of sales management administration (forecasting, territory reviews, etc.)
• Comfort with rolling out and reinforcing both sales process and sales methodology across the team
• Administer a repeatable daily/weekly/monthly management and selling cadence
• Exceptional in understanding how to motivate a sales team and achieve a consistent level of intensity and focus, each day
• Focus on the ongoing career development of direct reports to help get them ready for larger challenges and future responsibilities
• Successfully hiring, on-boarding, and coaching new team members

What you’ll bring

• 10+ years of experience in sales, with at least 3 years in a leadership role
• Automotive and specifically, Inventory Management, experience would be a preference
• Demonstrated history of exceeding revenue targets, building high-performing teams, and driving sustained growth in fast-paced environments.
• Strong strategic thinking – with the ability to craft and execute go-to-market strategies and scale sales operations effectively.
• Experience hiring, mentoring, and developing sales teams across different functions, with the ability to inspire and motivate both individuals and teams.
• Proficiency in using CRM platforms (e.g., Salesforce) and sales analytics tools (Gong) to monitor performance and inform strategy.
• Strong cross-functional collaboration skills — able to partner with product, marketing, and customer success teams to align on objectives and deliver impact.
• Excellent verbal and written communication abilities
• Awareness of current trends in technology, digital transformation, AI, cloud services, or other relevant sectors, and the ability to translate these into commercial opportunities.
• Preference for this candidate to be located in or around our Boston headquarters

Role overview

CarGurus is seeking a Senior Product Manager, Vehicle Acquisition to join our growing Dealer Product team. You will be part of a group that is building innovative tools to solve one of auto dealers’ biggest problems: quickly, confidently, and profitably acquiring used vehicles for their inventory. In this role you will lead development to evolve and build new dealer products that allow dealers to source inventory directly from shoppers. 

You’ll interface closely with dealers and internal stakeholders, including Engineering, Design, Data Science, and GTM, to transform ambiguous opportunities into high impact product strategy. By validating hypotheses and uncovering deep customer insights, you’ll prioritize and execute opportunities that solve real-world pain points for dealers while driving measurable growth for CarGurus. 

As a high-ownership strategic thinker, you’ll take full accountability for your product’s outcomes. You are a clear, candid communicator who can translate complex technical wins and challenges into a compelling narrative for leadership and the broader organization. Are you ready for the ride?

If you are a high-ownership strategic thinker who is excited about creating intuitive, powerful intelligence products for dealers, we’d love to hear from you!

What you'll do

• Own the roadmap and strategy for Vehicle Acquisition at CarGurus, ensuring alignment with business goals, dealer needs, and broader initiatives.  
• Become the go-to expert at CarGurus on how dealers make sourcing, stocking, and other acquisition decisions – and how they should in the future.
• Guide cross-functional teams through rapid end-to-end cycles of ideation, design, development, launch, and optimization of innovative products and high-impact features.
• Distill and decompose complex problems and business opportunities into product requirements and priorities, enabling clarity, focus, and iterative delivery and learning. 
• Collaborate with Engineering, Design, Data Science, and Product Data Analytics teams to develop rich, reliable data sets and predictive insights, then translate them into intuitive product experiences.
• Collaborate with Sales, Marketing, Customer Success, and other GTM stakeholders to launch, grow adoption of, and support new revenue-driving products and features.
• Create frequent opportunities to learn from dealers; through feedback on live software, usability studies, market analysis, and engagement with internal expertise.
• Continually analyze the impact of your teams’ work on dealers and on the CarGurus business. Use data to inform and advance the success of our products.

What you'll bring

• 5+ years of experience in fast-paced, dynamic environments working collaboratively with engineering, design, and analytics teams.
• Previous experience launching and managing B2B products in high-ownership environments.
• Highly curious, with the desire to learn rapidly, adapt quickly, and continuously improve. 
• A proven ownership mindset paired with the drive to lead a product area to success.
• Demonstrated customer empathy with the ability to quickly understand a problem space. 
• Systems thinker who is comfortable creatively solving problems in unstructured, fast-paced environments. 
• Excellent verbal and written communication skills, with experience collaborating with both technical and non-technical teams
• The ability to effectively collaborate and partner with internal teams and interface directly with our dealer customers
• Analytical, with a high level of data fluency.

Role overview

CarGurus is seeking a Senior Product Manager to lead the end-to-end consumer marketplace experience within our International Product team. As one of the fastest-growing areas of our business, this role offers a high-ownership opportunity to scale our global presence in a rapid, entrepreneurial environment.

In this role, you’ll sit at the intersection of consumer needs and dealer success, uncovering high-impact opportunities in a fast-paced, unstructured environment. You’ll collaborate with cross-functional experts to validate hypotheses, prioritize bold initiatives, and deliver products that grow the CarGurus business. If you enjoy working across a variety of different focus areas to drive global impact, we’d love to hear from you!

What you'll do

• Own the roadmap and strategy, ensuring alignment with business goals, consumer needs, and broader initiatives.  
• Guide cross-functional teams through rapid end-to-end cycles of ideation, design, development, launch, and optimization of innovative products and high-impact features.
• Distill and decompose complex problems and business opportunities into product requirements and priorities, enabling clarity, focus, and iterative delivery and learning. 
• Partner with Engineering, Design, Data Science, and Product Data Analytics teams to transform insights into actions
• Collaborate with Sales, Marketing, Customer Success, and other GTM stakeholders to launch, grow adoption of, and support new revenue-driving products and features
• Continually analyze the impact of your teams’ work on consumers and on the CarGurus business. Use data to inform and advance the success of our products.

What you'll bring

• 5+ years of experience in fast-paced, dynamic environments working collaboratively with engineering, design, and analytics teams.
• Previous experience launching and managing consumer products in high-ownership environments.
• Highly curious, with the desire to learn rapidly, adapt quickly, and continuously improve. 
• A proven ownership mindset paired with the drive to lead a product area to success.
• Demonstrated customer empathy with the ability to quickly understand a problem space. 
• Systems thinker who is comfortable creatively solving problems in unstructured, fast-paced environments. 
• Excellent verbal and written communication skills, with experience collaborating with both technical and non-technical teams
• The ability to effectively collaborate and partner with internal teams
• Analytical, with a high level of data fluency

Role overview

Your job is simple to say, hard to do: help create the growth and development environment where Account Management leaders can become world-class coaches. You do that by spotting what works, sharpening how managers coach, and turning good ideas into repeatable habits on the team.

You embed in and align with the Inside, Field, and National Account Management teams as a peer resource to our managers. You help them see the work more clearly, coach more directly, and use our tools and frameworks the right way.

This is a high‑visibility role. People across the Revenue organization will see and know your work. You’ll have the opportunity to lead large group trainings, team specific workshops, and small group coaching sessions we call “Growth Labs”.

What you'll do

• Pick the right problems. Use churn performance data, client engagement data, and live conversational insights to find the biggest wins for Account Management teams. Turn those into clear coaching opportunities that support our revenue objectives.
• Make our Engagement Frameworks Real: Help managers coach their teams with our Value‑Based Selling & Servicing frameworks.
• Coach the coaches: Join manager coaching sessions, listen to calls, and help leaders turn fuzzy feedback into sharp coaching moments they can repeat every week.
• Stand up simple routines. Build light, repeatable cadences—scorecards, check‑ins, labs—that help managers watch the right numbers and the right calls without drowning in dashboards.
• Support onboarding. Work with Enablement and Revenue Onboarding so new AMs learn our customers, tools, and playbooks the same way, every time.
• Tell the story. Share what’s working and what’s not with directors and cross‑functional partners in plain language: here’s the problem, here’s what we tried, here’s what changed and here’s what we learned.

What you'll bring

• You’ve developed in a quota‑carrying B2B Account Management, Customer Success, or Sales role and performed in the top 25% of your peer set. You know what good looks like on the floor.
• You’ve run books of business, managed renewals or expansions, and lived with a target. You care about churn, deal health, and product mix because you’ve been paid on them.
• You may or may not carry the title today, but you think like a manager. You’ve led pods, mentored reps, or managed teams and want to spend more of your day making other people better. (Direct people‑management experience is preferred.)
• You can push leaders and partners without a title. You’ve influenced cross‑functional stakeholders without direct authority.
• You’re comfortable in Salesforce, and Call Intelligence platforms like Gong. You can pull your own views, spot a pattern, and turn it into a simple coaching prompt or checklist.
• You speak and write in plain language. Short sentences with actionable insights and clear asks.
• You like being where the action is. You’re expected to meet and exceed 60% in‑office time and you use that time to sit with managers, join meetings, and listen to calls.

If you like solving hard problems with managers, care about growing our dealer business, and enjoy turning good reps and leaders into great ones, this role is for you.

Role overview

CarGurus' Dealer Competitive Intelligence team is seeking a Software Engineer II (Full Stack) to drive the next generation of analytics, data products, and dealer-facing experiences. This role offers a wide array of opportunities to work across the stack as we build a new dealer-facing product from the ground up. To succeed in this role, you must be able to learn and adapt quickly while collaborating effectively with a cross-functional team.

What you'll do

• Develop and deploy clean, well-tested and efficient code, ensuring high standards of architecture, quality and performance
• Provide support and improvements to core systems while maintaining high standards for internal stakeholder teams 
• Collaborate with cross-functional teams, including data analysts and product managers, to guide projects from concept through technical design, implementation, quality testing, and performance measurement

What you'll bring

• 2-4 years of hands-on software development experience in a professional setting
• Proficiency in React and Javascript fundamentals
• Proficiency in Java, SQL
• Proficiency in AWS / AWS Certification preferred
• Experience or interest in leveraging AI coding tools
• Practical knowledge of distributed systems and microservice architecture design
• A strong understanding of data structures, algorithms and complexity analysis
• The ability to iterate and ship ideas quickly and independently
• Demonstrates curiosity and a passion for learning new technologies and concepts quickly

Role overview

We are hiring for a backend engineer in our Consumer organization to drive our consumer-facing experiences forward. Consumer is the core functionality of our business that consumers see and use. We build features and develop solutions to drive our consumer-facing experiences forward.

The Consumer Mobile App team is rebuilding and reimagining our entire user experience to help our customers find the perfect car for them, at a fair price. You will have the opportunity to realize this vision, building out mobile-focused features to make our app fast, responsive, and flexible. You will be building net-new features for our most engaged audience.

What you'll do

• Collaborate with fellow engineers, designers, product managers, and analysts to take an idea from concept to technical design to implementation to testing to measurement
• Drive impact forward. This could be anything from implementing a new full consumer facing feature, to integrating with a key partner or technology
• Be deeply engaged in the full development lifecycle designing, developing, testing, deploying, maintaining, monitoring and improving software
• Investigate, identify, and implement API performance enhancements
• Advocate for new technology and new methodologies
• Continuously learn and expand your capabilities

What you'll bring

• 2-5 years of hands-on software design and development experience
• Expert in OOP (Java required), ideally in fast paced environments
• Solid experience in the data layer including SQL, caching strategies, and storage alternatives
• A strong understanding of data structures, algorithms and complexity analysis
• Experience working with web tier technologies and strategies
• Experience working in cross-functional teams with front-end engineers, Product, and UX
• The ability to iterate and ship ideas quickly
• Experience with A/B testing and/or performance testing
• Experience with AWS
• Bachelor’s degree in Computer Science or Computer Engineering

Role overview

We are seeking a Benefits Analyst to be based in our Boston, MA, global headquarters location. This role will be reporting to the Director of Benefits and will be responsible for the oversight and administration of several CarGurus’ North America Benefits programs and perks as well as heavy involvement in new initiatives. This role will collaborate closely with both internal and external stakeholders and partners to optimize benefits offerings and provide excellent service to employees.

What You’ll Bring

• 5+ years of U.S. benefits experience, preferably in fast paced, growing tech environments.
• Experience in most functions of employee benefits administration including health and welfare, well-being, life and disability, leaves, 401(k), and voluntary plans. Time off, leaves and accommodations administration experience, as well as a passion for well-being are a plus.
• Proven examples of independently owning several areas of benefits responsibilities, including careful tracking, accountability and clear communication with all critical stakeholders a must.
• Examples of working collaboratively in a team environment.
• Affinity for educating and communicating on employee benefits, including presenting to audiences.
• Appreciation for compliance and risk reduction with comfort in and knowledge of local, state and federal employee benefits regulations, such as ERISA, IRS, DOL, ACA, HIPAA, and COBRA.
• Examples of successfully completing special projects on top of normal day to day responsibilities.
• High level of integrity and discretion when handling sensitive employee information.
• Robust analytical skills, with the ability to interpret data and make data-driven recommendations.
• Attention to detail and accuracy.
• Comfort and proficiency with computer software and HRIS systems (Google products and Workday experience a plus).

What you’ll do 

• Own day-to-day administration of assigned benefits programs, with a primary focus on leave of absence, disability, and accommodations.
• Manage leave and accommodation cases end-to-end, partnering with vendors to ensure timely and accurate execution, and clear collaboration and communication with HR Strategy Partners, claimant employee and their manager.
• Provide guidance and education to employees and managers; act as a subject matter expert on benefits programs.
• Monitor vendor performance, data, and reporting; identify issues and hold partners accountable to service levels.
• Collaborate cross-functionally (People Operations, People Applications (HRIS), Payroll, Legal, vendors) to ensure smooth program delivery.
• Maintain confidentiality while ensuring compliance with legal and company requirements.
• Support audits, reporting, and analysis; identify trends and recommend improvements.
• Contribute to projects and program enhancements, vendor RFPs, and key initiatives like Annual Open Enrollment.
• Partner with the Benefits team to meet priorities and escalate when needed.
• Create employee communications for assigned programs.
• Maintain ~60% onsite presence, with flexibility during peak periods.

Role Overview 

The Sales Commissions team is looking to hire an experienced, highly motivated Senior Commission Systems and Data Analyst, to help shape the future of the CarGurus commission team. This role will partner with the commission team in driving decision-making and results through detailed analysis and data modeling. Reporting to the Director of Sales Incentives, this specialized role will closely collaborate with the Go-To-Market (GTM) team, along with other departments, to support the company’s strategic objectives while maintaining accurate and predictable commission processes. 

The successful candidate will specifically demonstrate a strong aptitude for interpreting, analyzing, and optimizing complex commission systems, and independently identifying opportunities for system enhancements. Technical problem-solving, prioritization, and attention to detail are critical.  This position offers multiple opportunities to showcase systems analysis and technical skills.

As a core member of the Commission team, this person will be responsible for supporting our commission administration, processes and reporting deliverables.

What You'll Do

• Manage and maintain Captivate IQ software, overseeing the commission team’s operations, processes, and related procedures.
• Ensure timely and accurate calculation and distribution of commission payments with an analytical mentality and close attention to detail.  
• Utilize Captivate to streamline processes and improve accuracy.
• Develop and automate dashboards, stack rank, plan health, and other reports using best-practice reporting processes.
• Assist with modeling and reporting for all commission deliverables.
• Ensure SOX compliance and manage SOX and accrual reporting.
• Respond to ad hoc analyses, special projects, and other similar or related duties as required or requested.
• Manage commission cases, ensuring timely resolution and communication.
• Provide Captivate IQ technical support and training to all stakeholders
• Create, develop, and implement repeatable business, operational, and financial processes, partnering closely with the commission team, to identify key areas of improvement for maximum efficiency.
• Own end-to-end Customer Growth and Retention (CGR) operations in Salesforce, including monitoring the SO CGR queue, validating and updating CGR records (existence, negative deltas, cancellations, ownership), performing weekly and quarter-open/close audits, and ensuring CGR data is accurate and complete for payouts.
• Serve as the CGR policy and process point of contact for Sales, reviewing CGR-related inquiries, applying CGR policy across Accounts/Opportunities/CGR objects, communicating rationale to reps and managers, and escalating complex issues to Sales Operations/EA as needed.

What You'll Bring

• Bachelor’s degree in finance, accounting, business administration, or a related major required.
• Minimum 4-5 years of relevant experience, ideally working closely with commission management, sales operations, or finance, preferably in a global context.
• Technical experience with Captivate IQ or a similar commission tool is strongly preferred.
• Hands-on Salesforce experience (accounts, opportunities, and custom objects), including data updates, queue management, and basic audits.
• Experience supporting sales incentive/commission or quota-crediting processes, including interpreting and applying policy in rep-facing communications.
• Proficiency in Excel, Google Sheets, Salesforce, or similar tools.
• Ability to project manage multiple tasks and priorities in a fast-paced environment.
• Consistently demonstrate behaviors that reflect initiative, intelligence, strong attention to detail, and integrity in striving for continuous improvement.
• Excellent written and oral communication skills, including the ability to present ideas and suggestions clearly and effectively.
• Ability to work independently.

Role overview

CarGurus is seeking an Associate Corporate Counsel to join our Legal team and support a dynamic, fast-growing technology company. This role will focus primarily on labor & employment matters, while also contributing to litigation and claims management as well as broader regulatory compliance efforts. 

This is an exciting opportunity for a thoughtful, business-minded attorney who enjoys solving complex problems, partnering closely with stakeholders, and delivering practical legal guidance that drives smart decision-making. You will play a meaningful role in supporting our People & Talent organization and helping CarGurus navigate an evolving legal landscape with confidence and integrity.

What you'll do

• Provide day-to-day legal advice on labor & employment matters, including hiring, discipline, performance management, terminations, leaves of absence, accommodations, and employee relations issues.
• Advise on compliance with federal, state, and local employment laws (e.g., wage and hour, discrimination, harassment, retaliation, leave laws).
• Deliver clear, practical, and timely legal advice to senior leaders within the People & Talent organization, demonstrating sound judgment, confidence, and the ability to translate complex legal concepts into actionable business guidance.
• Draft, review, and update employment-related documents, including offer letters, employment agreements, separation agreements, policies, and handbooks.
• Partner closely with the People & Talent team on investigations, policy interpretation, and risk mitigation.
• Support employment-related aspects of corporate initiatives, including reorganizations and M&A activity.
• Monitor legal developments and help implement practical compliance strategies and training.
• Strategic management of employment and commercial litigation, including coordinating with outside counsel.
• Conduct early case assessments to determine risk and drive cost-effective resolutions.
• Support discovery, document preservation, internal fact investigations, and case strategy.
• Conduct active oversight of legal spend and outside counsel efficiency.
• Support responses to government inquiries and subpoenas.
• Monitor relevant law and regulations to enable a proactive compliance posture.
  
  

What you'll bring

• J.D. from an accredited law school and active bar membership in at least one U.S. jurisdiction.
• 3-5 years of relevant labor & employment experience, including experience advising business clients and managing employment-related disputes.
• Strong working knowledge of U.S. federal, state, and local employment laws and regulations.
• Experience supporting or managing litigation matters.
• Prior in-house experience at a technology company or within a high-growth, fast-paced environment is a plus.