Guild is hiring a Security Engineer. The Information Security team is looking to add a highly motivated and technically inclined individual to work as a Cloud Security Engineer. We are looking for a candidate that is comfortable working in an exciting and fast paced environment. This individual’s responsibilities will mainly focus on ensuring protection of Guild’s various cloud resources and environments. These efforts will ultimately allow Guild to fulfill its mission while also meeting business objectives and compliance requirements.

As a Security Engineer, you will:

• Identify security issues and risks with Guild’s systems and environments. Develop and execute remediation/mitigation plans that provide long term risk reduction.
• Collaborate with cross-functional engineering teams to integrate and advance security standards within a comprehensive enterprise application security program.
• You will serve as a strategic partner to engineering squads, providing expert guidance on the integration and remediation of findings from SAST, DAST, and SCA tools.
• You will design and enforce robust security architectures across the company’s AWS ecosystem.
• Architect and implement security controls for agentic AI systems, including identity, network, and runtime-level defenses (e.g., sandboxing, policy enforcement).
• Develop comprehensive threat models and conduct realistic threat simulations across Guild's offerings, including LLMs, AI agents, and MCP components.
• Develop and tune security policy within various security tools and platforms (CNAPP, EDR, Email Gateway, Vulnerability Management, SIEM, etc…).
• Maintain SOC-2 compliance and assist with audit/client related requests. Assist with incident response and investigation activities.
• Fulfill regular on-call responsibilities as part of a team rotation.

You are a strong fit for this role if you have:

Required Competencies

• Thorough understanding of Integrated Development Environment (IDE) and Continuous integration / Continuous Delivery (CI/CD) Pipeline tools and processes
• Proven experience with software development methodologies and secure coding practices
• 5+ years of industry experience in security engineering, with meaningful focus on cloud security and application security
• Excellent problem-solving and analytical skills. Strong communication skills, both written and verbal, for collaborating with technical and non-technical teams. 
• Ability to work independently, prioritize tasks, and manage multiple security projects simultaneously.

Preferred Competencies

• Solid understanding of LLMs, AI architecture patterns, machine learning models, and related technologies (e.g., MCP, RAG, agentic frameworks)
• Experience with container security, kernel-level hardening, and modern isolation techniques.
• AWS Certifications

We are committed to equal pay for equal work and believe in compensation transparency. All salary ranges are standardized nationwide and will not vary by region. This role offers a competitive total compensation package, including a base salary of $150,000 - $180,000 and stock options. Compensation offered will be based on a combination of factors such as experience, competencies, and internal equity.

Posting Date: May 6, 2026

Guild is seeking a Senior Software Engineer II to join our Member Experiences pillar, focused on enhancing the scalability, flexibility, and reliability of our client data onboarding and integration systems. In this role, you will design and deliver robust software solutions that serve the evolving needs of our Employer Partners and the employees they support.

We’re looking for a self-driven, product-minded engineer who thrives in fast-paced environments and is comfortable navigating ambiguity. You will collaborate cross-functionally with internal stakeholders to develop adaptable, high-impact systems that help our partners deliver seamless access to Guild’s education benefits and coaching services.

As a senior member of the team, you’ll contribute from day one; crafting high-quality, scalable solutions that can keep pace with Guild’s rapid growth and the dynamic volume of client and user needs.

As a Senior Software Engineer II, you will:

• Develop and maintain robust software systems that power core member experiences; ranging from user-facing applications to internal tools and supporting service layers; ensuring performance, maintainability, and adaptability.

• Partner with senior and staff engineers to design modular, observable, and secure architectures that scale with Guild’s growth and accommodate evolving business needs and high-volume client demands.

• Write clean, testable, and reusable code. Contribute to end-to-end development including testing, CI/CD pipelines, monitoring, and deployment, ensuring high availability and quality in releases.

• Lead by example in code quality, technical decision-making, and documentation practices. Create and contribute to design documents, architecture decision records (ADRs), and technical discussions that communicate trade-offs clearly.

• Work closely with product managers, designers, operations teams, and external client technical teams to translate business requirements into effective engineering solutions. Contribute to planning, estimation, and execution of product roadmap items.

• Use operational data; such as logs, metrics, and user feedback; to identify and implement enhancements in performance, reliability, and developer velocity. Take ownership of resolving issues and driving root cause analysis and sustainability.

• Improve internal development processes, tools, and workflows to enhance code quality, speed of delivery, and system security.

• Participate in on-call rotations and incident response. Provide constructive code reviews and mentorship to help elevate teammates and build a high-performing engineering culture.

You are a strong fit if you have:

• 5+ years of software development experience with: Python, TypeScript, Node.js, React, PostgreSQL, DynamoDB, and GraphQL

• Hands-on experience with: AWS services, including Lambda, Serverless Framework, Glue, API Gateway, and CDK or other Infrastructure-as-Code (IaC) tools

• A deep understanding of: the full software development lifecycle; from gathering technical requirements and selecting technologies to deploying and maintaining production systems

• AI Experience:  Utilizing AI-assisted development tools such as Cursor, GitHub Copilot, or similar; Experience integrating LLM APIs (e.g., OpenAI) and building AI-powered features, including assistants, summarization, RAG workflows, and vector search

Ideal Candidate Qualities:

• Demonstrated success working in a production AWS microservices environment

• Ability to write simple, clean, and maintainable code

• Brings thoughtful technical opinions, but remains open to new perspectives (“strong opinions, loosely held”)

• Willingness to take calculated risks and contribute vision and direction to both the team and Guild as a whole

• A mindset of continuous learning and improvement

• A genuine passion for Guild’s mission and long-term impact

• Excellent collaboration skills; able to work cross-functionally, share knowledge, and foster team alignment

We are committed to equal pay for equal work and believe in compensation transparency. All salary ranges are standardized nationwide and will not vary by region. This role offers a competitive total compensation package, including a base salary of $160,000 - $195,000 and stock options. Compensation offered will be based on a combination of factors such as experience, competencies, and internal equity.

Posting Date: May 4, 2026

*This role will stay open for a minimum of 3 days. 

Please note this is a remote role with preference for candidates based on Eastern or Central Time due to location of clients.

We are seeking a dynamic and strategic Senior Account Director (Healthcare) to drive new business acquisition for our organization by advocating for the strategic value of education benefits to enterprise healthcare organizations, including hospital systems, health insurers, and other Fortune 500 healthcare companies.

As a Senior Account Director, you will initiate and maintain senior-level client relationships, understand their unique business goals, and close net new business. You will navigate complex sales structures end-to-end, utilizing a variety of strategies such as prospecting, call planning, account planning, and organizational mapping to drive positive outcomes.

Key Responsibilities:

• Build relationships with C-suite executives and senior level leaders at enterprise healthcare organizations to identify opportunities and drive revenue growth
• Partner with internal teams (e.g., BDR, ABM) to prospect and maintain a robust pipeline of opportunities
• Use data-driven insights to craft tailored solutions that address operational, clinical, or administrative challenges in the healthcare sector
• Design and deliver customer-facing presentations and proposals focused on tangible outcomes and value
• Cultivate internal champions within accounts to ensure broad support and alignment on decision-making processes
• Work cross-functionally with internal partners to design tailored programs, deliver executive presentations, and scope projects aligned with healthcare organizations’ needs
• Lead contract negotiations for sophisticated, high-value deals
• Develop detailed account plans and executive briefing documents to guide account strategy and pipeline management
• Adapt strategies based on evolving offerings and market conditions

Ideal Candidate Qualifications:

• 7+ years of field sales experience at the enterprise level, preferably within healthcare or related industries
• Proven success managing and closing complex sales cycles within healthcare organizations or Fortune 500 accounts (bonus for experience selling to CHROs, HR, or C-level healthcare executives)
• Knowledge of healthcare organizations, employee benefits, or operational challenges within healthcare
• Experience navigating healthcare compliance requirements and regulations during the sales process
• Experience with large contract values ($1M+) and a consistent track record of exceeding quota
• Familiarity with selling into highly regulated industries, such as healthcare
• Exceptional organizational, consultative, and presentation skills, with a strategic mindset and a structured approach to client engagements
• Experience in a fast-paced, high-growth or ever-evolving environment
• Ability to create urgency with clients and internal stakeholders, paired with a persistent drive for results

We are committed to equal pay for equal work and believe in compensation transparency. All salary ranges are standardized nationwide and will not vary by region. This role offers a competitive total compensation package, including a base salary of $175,000 plus significant commissions eligibility as well as company stock options. Compensation offered will be based on a combination of factors such as experience, competencies, and internal equity.

Posting Date: Apr 29, 2026
*This role will stay open for a minimum of 3 days. 

Guild is hiring a Senior Account Director – Public Sector based in the above states to help advance the next frontier of workforce education and career mobility. As a key member of our Public Sector Team, you’ll play an important role in identifying, assessing, and helping operationalize growth opportunities that expand Guild’s reach—particularly through partnerships with innovative states and local municipalities to support outcomes-based workforce development initiatives.

This is a strategic and execution-oriented role with a strong emphasis on building and owning relationships. You’ll contribute hands-on to shaping early-stage public-sector opportunities—from research and discovery through pilots and early scaling—while collaborating closely with the Vice President of Public Sector and cross-functional partners. You’ll help bring new opportunities to life and support Guild’s mission by unlocking partnerships at the state and local level.

This role is well-suited for a strategic operator and relationship-builder who is comfortable with ambiguity, enjoys building from scratch, has experience managing complex public-sector accounts, and is passionate about expanding access to education and economic opportunity.

Key Responsibilities:

Market Research & Opportunity Identification

• Conduct market research to surface and assess new public-sector opportunities across funding ecosystems and priority geographies.
• Analyze regulatory environments, policy trends, and local, state, and federal funding programs to inform account strategy and market entry approaches.
• Support the development and testing of market hypotheses and opportunity concepts within assigned territories or accounts.
• Synthesize research findings into clear insights to inform account planning and growth strategy.

Account Development & Origination

• Partner with B2B Marketing and Public Sector leadership to help originate and shape new public-sector accounts and expansion opportunities (0→1 and early growth).
• Build and manage relationships with state and local stakeholders to understand needs, constraints, and alignment with Guild’s capabilities.
• Apply established frameworks to evaluate opportunity fit, strategic value, and scalability within the Guild ecosystem.
• Contribute to go/no-go assessments and prioritization decisions based on early signals of traction, feasibility, and mission alignment.

Opportunity Validation & Solution Design

• Lead or support early engagements, pilots, and proof points to validate demand, feasibility, and impact within public-sector accounts.
• Collaborate with funders, partners, and beneficiaries to refine value propositions and solution design.
• Support the development of business models and funding structures aligned with Guild’s impact and financial objectives for state and local buyers.

Go-To-Market Execution & Account Growth

• Partner cross-functionally (marketing, product, learning marketplace, government affairs, operations) to translate validated opportunities into executable go-to-market plans
• Help define and track key success metrics and leading indicators of account health and market traction, including revenue and total education spend.
• Support early GTM execution by sharing real-time market feedback and identifying where additional local engagement or advocacy may be required.

Cross-Functional Collaboration & Strategic Support

• Work closely with internal teams such as Finance, Legal, Policy, and Product to ensure public-sector opportunities are viable, compliant, and scalable.
• Contribute to structuring and managing strategic partnerships that support account growth.
• Provide clear, data-informed insights to senior leaders to support decision-making and prioritization.

You are a strong fit for this role if you have:

• 7–10+ years of experience in account management, business development, strategy, consulting, or sales roles, ideally within government, workforce, education, or mission-driven sectors.
• Experience managing complex, multi-stakeholder accounts—particularly with public-sector or quasi-public entities.
• Demonstrated ability to help build and grow new accounts or programs from the ground up.
• Strong analytical and problem-solving skills, with experience supporting business cases, market analysis, or financial models.
• Experience supporting pilots, implementations, or new initiatives in ambiguous or evolving environments.
• Comfort engaging with senior-level external stakeholders, including government officials, funders, and mission-aligned partners.
• Strong communication skills with the ability to translate complex ideas into clear recommendations.
• Alignment with Guild’s mission to unlock opportunity through education and career pathways.

We are committed to equal pay for equal work and believe in compensation transparency. All salary ranges are standardized nationwide and will not vary by region. This role offers a competitive total compensation package, including a base salary of $175,000, plus variable compensation, commission, and stock options. Compensation offered will be based on a combination of factors such as experience, competencies, and internal equity.

Posting Date: April 15, 2026

*This role will be open for a minimum of 3 days.

Location: Remote (US) — must be available for 7am–4 pm Mountain Time shift OR 11am–8 pm Mountain Time shifts; geographic distribution across the US preferred 

Commitment: 40 hours/week

Type: Full-time

About Guild:

Guild partners with the country's largest employers to offer education and coaching as a benefit to their employees. Our coaches are at the heart of that mission — they're the human connection that helps working adults navigate real change in their lives. We support learners who are balancing jobs, families, and school, often for the first time, and our coaches make the difference between someone giving up and someone crossing the finish line by deploying empathy, accountability, and career services.

We're growing our coaching team and looking for experienced coaches (career and executive coaches) who are ready to bring their full practices to a mission-driven environment—and who want to do so at scale.

The Role:

As a Senior Guild Coach, you'll carry a caseload of learners enrolled through our employer partners, partnering with them to identify and accomplish goals that align with their academic and career aspirations. You'll bring your full coaching toolkit — advanced techniques, cultural competency, and a bias toward learner empowerment — while also contributing to the broader coaching team as a collaborator.

This is a role for coaches who are entrepreneurial by nature: people who've built or run their own practice, who don't need to be managed closely, and who are energized by figuring out what approaches to deploy to maximize the number of learners served annually. You'll be joining a team that's actively evolving — integrating AI-augmented coaching tools, refining how we measure impact, and pushing the boundaries of what it means to coach at scale without sacrificing quality.

What You'll Do:

Coach learners with depth and consistency

• Partner with learners to identify, refine, and accomplish goals aligned with their academic and career aspirations, using advanced coaching techniques and strategies
• Approach every conversation with a culturally aware lens, adapting your coaching practice to each learner's needs, values, preferences, and identity
• Manage your assigned caseload with strong organization and consistent outreach, ensuring no learner falls through the cracks
• Maintain accurate records of coaching sessions, learner progress, and outcomes to enable proactive, personalized support
• Continually develop and apply best practices that improve the experience — especially for our most under-resourced learners

Drive engagement and retention through smart use of data and tools

• Use tools and data to develop scalable strategies that generate high learner engagement and persistence
• Balance caseload management with broader leadership contributions across the department

Strengthen the coaching department through insights and expertise

• Collaborate with coaching leadership and cross-functional teams to identify trends and opportunities for process improvement
• Contribute to department-wide initiatives that enhance the efficiency and effectiveness of Guild Coaching
• Stay current on industry trends and best practices; bring outside perspective into how we coach

What We're Looking For:

Experience

• 3+ years of career coaching and/or executive coaching experience or 500+ hours of coaching experience
• Demonstrable track record supporting diverse, non-traditional clients — with the ability to adjust style and tactics to meet unique needs and support learner persistence
• Proven history of positive learner/client outcomes, with high goal achievement and strong feedback
• Experience collaborating with department or cross-functional leadership on strategic initiatives
• Proven track record of mentoring or coaching peers to success

Mindset and working style

• Possesses an independent, entrepreneurial spirit, potentially from managing a personal coaching practice; excels with high levels of autonomy and minimal supervision.
• Strong work ethic with personal accountability for performance and continuous improvement as both a leader and a coach: able to learn new skills, self-monitor, and self-correct
• Strong communication skills: able to give clear, actionable feedback and share ideas concisely
• Comfortable influencing at all levels, with strong stakeholder management and experience partnering with peers and leaders
• Committed to building equitable and inclusive environments for both learners and colleagues

Logistics

• Available to work 40 hours/week on a consistent basis
• Available for early Mountain Time shift (7am–4 pm MT) or late Mountain Time shift (11am–8 pm MT) — this is a firm requirement to serve our working adult learners
• US-based; we are intentionally building a geographically distributed team and welcome applicants from all regions

Additional Considerations

• Coaching or Career Services certification (preferred, not required)
• Experience with coaching in a tech-enabled or high-volume environment
• Familiarity with adult learner populations, workforce education, or career mobility programs

Why Guild:

• Mission that's tangible: you'll see and feel your impact on real people navigating real change
• A coaching team that takes craft seriously — we invest in your development and your ideas matter
• A dynamic environment with evolving tools, including AI-augmented coaching support, so you can focus your energy where it counts most
• Competitive compensation and benefits
• Flexibility to work remotely from anywhere in the US

We are committed to equal pay for equal work and believe in compensation transparency. All salary ranges are standardized nationwide and will not vary by region. This role offers a competitive total compensation package, including an hourly rate (non-negotiable) of $34.10 per hour, annual bonus potential and company stock options. 

Posting Date:

Tuesday, April 28

*This role will stay open for a minimum of 3 days. 

As the Director, IT, you will be the operational backbone of our technology ecosystem. Reporting to the Senior Director, IT, you will lead two critical pillars: IT Operations (Infrastructure & Backend) and IT Services (Employee Support & Experience). You aren't just "keeping the lights on"—you are architecting the infrastructure that supports a next-generation, AI-integrated workforce.

In this role, you will bridge the gap between high-level AI strategy and day-to-day technical stability, ensuring our internal systems are secure, scalable, and frictionless.

Key Responsibilities:

1. Strategic Leadership & Function Management
   • Define and execute the long-term roadmap for both IT Operations and IT Services, ensuring technology initiatives directly support business growth.
   • Provide high-level mentorship and professional development for the managers leading the Ops and Services functions.
   • Manage the IT budget, vendor partnerships, and SaaS license procurement/optimization in close collaboration with our APM team.
2. Cloud Infrastructure & "Agent" Readiness
   • Own the strategy for Cloud Identity & Access Management (IAM), ensuring a "zero-trust" approach to security.
   • Special Focus: Partner closely with the AI/Agent Engineering teams to architect the "Agent Infrastructure." You will ensure our internal AI agents have the secure, programmatic access they need to interact with our SaaS ecosystem and data layers.
3. Security, Compliance, and Governance
   • Serve as the primary owner for internal IT security posture (SSPM, endpoint protection, disaster recovery) in partnership with Infosec.
   • Lead IT’s role in compliance efforts (e.g., SOC2), ensuring all systems and access protocols meet rigorous audit standards.
4. Automation & Service Excellence
   • Drive a "zero-touch" philosophy for the employee lifecycle—automating onboarding and offboarding through deep integrations between HRIS (Workday), Identity (Okta/Azure), and our core SaaS applications.
   • Ensure the IT Services team maintains exceptional SLAs, providing a modern, "white-glove" support experience for a global workforce.
5. Incident Response & Operational Resilience
   • Own IT Incident Response: Serve as the primary point of escalation for critical service disruptions. You will establish the protocols for rapid identification, triage, and resolution to ensure minimal business impact.
   • Post-Incident Excellence: Drive a culture of "post-incident learning." You will oversee root-cause analysis (RCA) and blameless post-mortems to ensure we are continuously hardening our systems against future failures. 

Who You Are:

• The Experienced Leader: You have 7+ years in IT, with 3-5 years specifically leading other managers. You are an expert at empowering your leadership team to handle day-to-day operations while you focus on high-level technical and organizational strategy.
• Builder Instinct: You are excited by the "Agent Infra" challenge. You understand that the IT of 2026 involves managing both human users and AI agents.
• The Cloud Architect: You don't think in terms of servers; you think in terms of APIs, Integrations, and Identity. You have a proven track record of managing complex, SaaS-heavy environments.
• Automation-First Leader: You believe that if a manual task has to be performed twice, it should be automated. You have experience with workflow automation and IaC concepts.
• Modern Security Mindset: You treat security as a fundamental feature of great IT, not a hurdle. You are comfortable securing environments where both humans and AI agents are active users.

Qualifications:

• 7+ years of hands-on technical experience in IT infrastructure/operations, ideally in a growth-stage or mid-size SaaS/platform company
• 3+ years of people management experience in IT, including managing managers or multiple functional teams (ops + services)
• Strong foundation in identity and access management — Okta or equivalent
• Experience managing endpoint security, MDM strategy, network architecture, and ZTNA
• Working knowledge of NIST CSF, SOC 2, and SOX compliance requirements
• Proficient in scripting, API tools, and IT automation workflows
• Familiarity with the AI agent ecosystem: integration platforms, API authentication patterns, MCP servers, or similar agent-to-system connectivity tooling

Nice to Haves:

• Experience with Cloudflare Zero Trust, Twingate, or similar ZTNA platforms
• Hands-on experience with agent authentication patterns (OAuth for non-human identities, service accounts at scale)
• CISSP, CISM, or equivalent certification
• Experience with AI tooling governance — managing enterprise licenses, usage policies, and security controls for AI products

The Pillars You'll Lead:

• IT Operations (Core Platforms & Infrastructure): Focused on the "digital backbone"—SaaS orchestration, cloud identity (IAM), security engineering, and automated provisioning. This team ensures our cloud environment is secure, integrated, and scalable.
• IT Services (Employee Experience): Focused on the "user layer"—the service desk, hardware lifecycle management, and ensuring technology is an enabler, not a hurdle, for our employees.

Success in 6 Months Looks Like:

• You have established a high-velocity operational cadence across both the Operations and Services functions.
• The "Agent Infrastructure" roadmap is defined and being actively implemented in partnership with the AI team.
• You have completed a comprehensive optimization of our IAM and SaaS security workflows, significantly reducing manual overhead.

Why This Role Matters:

Every company is going to face the question of how AI agents interact with their enterprise systems. Most IT teams are still thinking about this as a future problem. At Guild, it's happening now — we have agents in production, an internal AI platform, and an executive team that's pushing the frontier. This role shapes how Guild builds the infrastructure for that future while keeping the fundamentals excellent.

Compensation:

We are committed to equal pay for equal work and believe in compensation transparency. All salary ranges are standardized nationwide and will not vary by region. This role offers a competitive total compensation package, including a base salary of $200,000-$225,000 PLUS variable (bonus) compensation eligibility and stock options. Compensation offered will be based on a combination of factors such as experience, competencies, and internal equity.

Posting Date: April 15, 2026
*This role will stay open for a minimum of 3 days. 

Guild is hiring a Principal Product Operations Manager for our Grow product area. This is the most senior individual contributor Product Operations role at Guild. This role sits at the intersection of product strategy, technical execution, and operational excellence - owning the systems, workflows, and delivery infrastructure that make Grow run, while leading high-impact strategic initiatives end-to-end alongside Engineering and Product leadership.

Responsibilities

Strategic Product Initiative Leadership

• Lead high-impact, cross-functional product initiatives end-to-end - from aligning teams and clarifying technical trade-offs to driving execution and measuring outcomes.
• Translate product strategy into concrete execution plans by working closely with Engineering leaders on architecture boundaries, dependencies, sequencing, and technical trade-offs.
• Own launch and release readiness across all stakeholders: teams are informed, equipped, and ready before anything ships.

Operational Design, Optimization, and Impact

• Develop and refine operational systems, tools, and AI-enabled workflows to enhance the efficiency of Product, Engineering, Design, and Data teams.
• Conduct regular audits of Grow’s R&D processes to identify friction, map system dependencies, and drive scalable improvements with clear operational standards.
• Build and maintain operational playbooks, escalation frameworks, and governance models.
• Establish operating cadences for Grow, with a bias toward reducing coordination overhead and protecting time for high-value work.
• Design and continuously evolve the end-to-end product delivery system for Grow - intake, prioritization, planning cadences, release readiness, and delivery standards.
• Define and own delivery performance metrics and dashboards; use data to identify trends, diagnose systemic issues, and validate impact of improvements.

AI Prototyping and Automation

• Identify where AI can be embedded across the product development lifecycle.Design and test AI-assisted workflows; validate impact before scaling broadly.
• Model responsible, high-leverage AI use for the broader P&E org.

Tool Evaluation

• Assess tooling gaps, lead vendor conversations, and ensure tools are appropriate, integrated, and adopted across Grow.

Cross-Functional Alignment

• Facilitate alignment across Product, Engineering, Design, Data, GTM, EPS, and Operations - ensuring priority clarity and seamless execution.
• Establish feedback loop infrastructure so customer, partner, and operational signals reach the roadmap systematically.
• Build communication norms and shared artifacts that scale across teams and reduce coordination overhead.

What We’re Looking For

• Systems thinking and technical acumen. You design operational systems that scale and understand how changes ripple across teams and platforms. Credible in rooms with engineers and architects - you understand architecture trade-offs, data flows, service dependencies, and when to go deep vs. zoom out to cross-team sequencing.
• AI-forward mindset. You have real opinions about where AI should and shouldn’t be applied in a product development lifecycle - and you’ve built or prototyped something with it. You don’t treat AI as a feature; you treat it as a lever.
• Ownership, not coordination. You drive outcomes. You step into gaps rather than route around them. When something is unclear, you make it clear.
• Executive communication. You distill operational and technical complexity for a VP without losing precision with an Engineering Director. You know what to escalate, what to absorb, and how to frame both.

Qualifications

• 12+ years of experience in Product Operations,Technical Program Management, Product Management, or a related role on Product Teams.
• Proven track record of designing and scaling product delivery systems across multiple teams or product areas.
• Experience leading cross-functional product initiatives end-to-end with accountability for outcomes.
• Hands-on experience designing or prototyping AI-assisted tools and workflows - not just familiarity with AI tools.
• Strong analytical mindset - you define metrics, build dashboards, and use data to drive decisions, not just report on them.
• Expertise with agile methodologies and associated tooling (Jira, Confluence, etc.).
• Experience operating autonomously at senior IC or staff level with demonstrated influence across engineering and product leadership.

We are committed to equal pay for equal work and believe in compensation transparency. All salary ranges are standardized nationwide and will not vary by region. This role offers a competitive total compensation package, including a base salary of $180,000 - $215,000, a bonus and stock options. Compensation offered will be based on a combination of factors such as experience, competencies, and internal equity.

Posting Date: April 21

*This role will stay open for a minimum of 3 days. 

*Please note this role is based in Denver, CO*

This role sits at the center of how Guild uses data to drive business decisions. As Senior Analyst, you'll own the KPI monitoring and insight generation that our executive team relies on to run the business, while also building the AI-powered tools and automated workflows that will enhance how the Analytics team operates for years to come. You'll bridge the gap between raw data and real decisions, partnering with Finance, Employer Partner Services, Product, and Marketing to ensure leaders can interpret, trust, and act on data with confidence. If you're excited about doing serious analytical work and building scalable systems that multiply the team's impact, this role was designed for you.

Outcomes Expected to Achieve:

• Executive-grade KPI intelligence: Leaders across the organization have a reliable, proactive source of truth on business performance, with clear interpretation of trends, risks, and forward-looking signals
• AI-powered analytics at scale: The Analytics team and its cross-functional partners spend less time on manual, recurring work because you've built tools and automations that handle it
• Analytical enablement across the org: Business teams can independently contextualize and act on data because you've made forecasts, metrics, and insights accessible and interpretable

Skills/Competencies required:

• SQL proficiency: you're comfortable writing complex queries across multi-table data models; dbt and Omni (or comparable BI tools) experience strongly preferred
• Applied AI fluency: hands-on experience building AI-powered tools or automating analytics workflows, not just familiarity with the concepts
• Executive communication: ability to distill complex findings into clear, confident recommendations for non-technical audiences
• Builder's mindset: you proactively identify opportunities to automate, scale, and improve how data is used; you don't wait to be asked
• Stakeholder partnership: comfortable consulting with cross-functional partners on scope, feasibility, and tradeoffs; can manage competing priorities and expectations
• Quantitative rigor: 4+ years in analytics, data science, or a related field, with comfort working across complex, multi-source datasets

Here's what you will do in this role to achieve these outcomes:

• Monitor business KPIs, identify risks and trends proactively, and deliver data visualizations and narrative insights that drive meaningful engagement with executive-level stakeholders
• Partner with the Forecasting & Financial Analytics team to bridge forecast outputs to day-to-day decision-making, enabling cross-functional teams to interpret and act on data with confidence
• Build and deploy AI-powered analytic solutions - automated reporting pipelines, repeatable Skill frameworks, and scalable tools - that reduce manual effort across the Analytics team and its partners
• Consult with stakeholders on reporting feasibility and scope; produce metrics and data structures that best meet their actual decision-making needs
• Deliver ad hoc analyses on Guild's business trends, member behavior, and learner and employer outcomes
• Write and maintain complex SQL, work within dbt models, and leverage Omni to surface and communicate data; partner with Data Engineering on data quality and schema requirements
• Evaluate and implement emerging AI tools and techniques to improve analytic workflows and stay current on the applied AI landscape
• Translate data on member experience, learner outcomes, and employer outcomes into external-facing thought leadership that supports business growth

You are probably a strong candidate for this role if you've accomplished:

• Built or automated an analytics workflow - reporting, alerting, or data pipeline - that meaningfully reduced recurring manual work for yourself or your team
• Delivered an analysis or data narrative to senior or executive stakeholders that influenced a strategic decision
• Applied AI tools or techniques in a practical analytics context. Not just experimented, but shipped something that stuck
• Worked across multiple complex data models and navigated ambiguous, multi-table datasets to produce reliable outputs
• Translated technical findings into clear recommendations that non-technical audiences could act on

We are committed to equal pay for equal work and believe in compensation transparency. All salary ranges are standardized nationwide and will not vary by region. This role offers a competitive total compensation package, including a base salary of $120,000 - $140,000 and stock options. Compensation offered will be based on a combination of factors such as experience, competencies, and internal equity.

Posting Date:

Thursday, April 23, 2026

*This role will stay open for a minimum of 3 days. 

Guild is seeking a highly skilled and proactive Senior Tax Manager to lead and manage our tax operations, with a strong emphasis on indirect taxes, including sales and use tax and local tax compliance. The ideal candidate will have comprehensive knowledge of general tax principles, proven experience in tax provision preparation under ASC 740, and exposure to M&A tax implications. This individual will be instrumental in working with third-party tax advisors, advising management on emerging tax issues, responding to ad hoc internal requests, and contributing to tax planning and optimization strategies.

Key Responsibilities

Indirect Tax Management

• Oversee all sales and use tax compliance, including registrations, filings, audits, and reconciliations.
• Manage local tax requirements, ensuring timely and accurate reporting across jurisdictions.
• Coordinate with third-party providers for accurate sales tax calculations, exemption certificate management, and jurisdictional compliance.

Tax Provision & Compliance

• Lead the quarterly and annual tax provision process in accordance with ASC 740, including calculation, documentation, and internal reporting.
• Ensure all federal, state, and local tax returns are prepared accurately and timely, in coordination with external tax service providers.
• Maintain tax balances in the general ledger and support the financial reporting team as needed.

Tax Advisory & Planning

• Monitor tax legislation and regulatory changes; evaluate the impact on the business and communicate potential risks/opportunities to leadership.
• Support tax planning efforts, including identification and analysis of opportunities for tax savings and process efficiencies.
• Provide tax input for mergers and acquisitions, including due diligence, structuring, and post-acquisition integration.

Cross-Functional Collaboration

• Act as the key liaison with external tax advisors, auditors, and consultants to ensure the accuracy and integrity of tax positions.
• Partner with Accounting, Legal, Finance, and Business Operations teams to assess the tax implications of business decisions.
• Lead or participate in special projects and ad hoc tax-related requests from senior management.

Qualifications

Required:

• 10+ years of tax experience with a blend of public accounting and industry roles preferred.
• Bachelor’s degree in Accounting, Finance, or related field.
• CPA, MST, or equivalent credential.
• In-depth knowledge of sales & use tax and other indirect taxes.
• Hands-on experience with ASC 740 tax provision preparation.
• Strong project management and organizational skills.
• Ability to communicate complex tax matters to both technical and non-technical stakeholders.

Preferred:

• Experience working with third-party tax software/tools (e.g., Avalara, Vertex, OneSource).
• Exposure to M&A tax structuring and due diligence.
• Familiarity with international indirect tax concepts (a plus but not required)

We are committed to equal pay for equal work and believe in compensation transparency. All salary ranges are standardized nationwide and will not vary by region. This role offers a competitive total compensation package, including a base salary of $180,000 - $200,000 and variable compensation (bonus) eligibility along with stock options. Compensation offered will be based on a combination of factors such as experience, competencies, and internal equity.

Posting Date: April 14, 2026

*This role will stay open for a minimum of 3 days.  

Principal Technical Program Manager - GROW

Guild is hiring a Principal Technical Program Manager for Grow Product, the most senior individual-contributor Technical Program Management role at Guild. In this role, you will drive execution across the technical foundations that support our multi-product organization while helping build the TPgM discipline from the ground up. This role combines deep technical leadership with program execution: leading critical company-wide initiatives, influencing architectural decisions across Guild’s technical stack, and shaping what technical program management means as we scale.

Responsibilities

• Assess the current state of Grow Product across business objectives, stakeholder needs, and delivery inhibitors, and translate findings into a long-term, multi-team execution roadmap in close partnership with Product and Engineering.
• Translate product strategy into concrete technical solutions and execution plans by working closely with engineering leaders to clarify architecture boundaries, dependencies, sequencing, and technical trade-offs.
• Own execution of the articulated roadmap by aligning teams, proactively managing dependencies, and ensuring predictable, high-quality delivery.
• Own launch and release readiness across all stakeholders, ensuring teams are informed, equipped, and ready before anything ships.
• Operate with full ownership across products, and programs. Proactively identify risks, blockers, decision gaps, and opportunities, resolving them directly or ensuring clear ownership and accountability.
• Help shape the TPgM craft at Guild by modeling technical excellence, strong ownership, and sound execution judgment, and by contributing to the standards and operating model as the function scales.
• Establish and evolve the operating cadences for Product and Engineering, including how teams plan, review, and align, with a bias toward reducing coordination overhead and protecting time for high-value work.
• Mentor TPgMs and Product and Engineering leaders, establish best practices, and scale program leadership capabilities across the Guild P&E organization.
• Champion AI adoption by identifying opportunities to embed AI into the Product Development Lifecycle and modeling effective, responsible use of AI tools.

What We’re Looking For

Technical Acumen and Cross-System Reasoning

• Working technical foundation with the ability to understand architecture, service boundaries, data flows, and technical trade-offs
• Demonstrated systems thinking: ability to reason about how changes ripple across teams and systems, and to think in sequences (e.g., dependency readiness, integration timing, and rollout order), not just individual projects
• Able to identify what needs to be measured and why, ensuring product data is trusted and actionable, and using data to surface risks and drive decisions
• Knows when to go deep and when to go broad, able to dive into technical details when a program is at risk, and zoom out to cross-team sequencing when alignment is the bottleneck

Ownership mindset and trust-building

• Proven track record of owning outcomes, not tasks.
• Proactively steps into ambiguity and execution gaps rather than routing around them.
• Builds credibility with Product and Engineering partners by understanding the “why,” anticipating issues, and acting as a true execution partner

Communication and Collaboration

• Communicates with precision across audiences — translates technical complexity for executives without losing credibility with engineers and architects
• Drives alignment in ambiguous, multi-stakeholder environments by creating clarity around decisions, owners, and sequencing
• Establishes feedback loop infrastructure that ensures customer, partner, and operational insights are systematically captured and inform product and roadmap decisions
• Establishes communication norms and shared artifacts that scale across teams and reduce coordination overhead

Qualifications

• 12+ years of experience on software teams as a Technical Program Manager, Engineering Manager, Product Manager, or similar role.
• Experience driving and delivering complex tech programs or products from inception to delivery
• Experience operating autonomously across multiple teams and functions, demonstrated critical thinking, and thought leadership
• Communication experience at executive level and experience influencing senior leadership and technical management teams to develop systems, solutions, and products
• Experience establishing work relationships across multi-disciplinary teams and multiple partners in different time zones
• Experience working with product teams to build and deliver end-to-end customer focused products with technical knowledge of the underlying platforms and technologies

We are committed to equal pay for equal work and believe in compensation transparency. All salary ranges are standardized nationwide and will not vary by region. This role offers a competitive total compensation package, including a base salary of $180,000 - $215,000, a bonus and stock options. Compensation offered will be based on a combination of factors such as experience, competencies, and internal equity.

Posting Date: March 2, 2026

*This role will stay open for a minimum of 3 days. 

We are seeking a strategic, data-driven, and creative Senior Marketing Manager - Guild Academy to lead high-impact marketing initiatives that drive brand awareness, customer acquisition, engagement, and revenue growth for Guild’s Academy product; B2B marketing to a Senior HR or L&D Enterprise buyer. This role will own key marketing programs end-to-end — from strategy and planning through execution and performance optimization — and partner cross-functionally to deliver measurable business outcomes.

The ideal candidate blends strong business acumen with hands-on execution, thrives in fast-paced environments, and has experience influencing senior stakeholders across functions.

Key Responsibilities

Strategy & Planning

• Translate product business requirements into marketing goals - with an emphasis on pipeline creation - in partnership with Marketing Operations, Product Marketing and channel teams (events, digital, social, etc.)
• Drive optimization recommendations and build performance mindset across the collective teams 

Campaign & Program Leadership

• Serve as ‘marketing quarterback’ with functional disciplines (thought leadership, content, events, etc.) to execute and optimize campaign and programs
• Partner with Operations team to prioritize metrics and drive performance outcomes
• Contribute to messaging strategy (with PMM) and ensure brand consistency across touchpoints
• Drive monthly and quarterly reviews to senior leadership team

Stakeholder & Team Leadership

• Build strong trusted partnerships with the key product leadership: PMM, Solution Consultants, Product and Sales 
• Influence and align cross-functional partners
• Champion best practices in marketing operations, experimentation, and execution
  
  

Qualifications

Required

• 6–10+ years of performance marketing experience
• Proven experience leading multi-channel marketing programs
• Strong strategic thinking and business acumen
• Demonstrated ability to translate data into insights and action
• Experience partnering closely with Sales and/or Product teams
• Exceptional project management and prioritization skills
• Excellent written and verbal communication skills
• Exceptional influence skills across business and marketing leaders
• Experience working in medium-sized or high-growth companies and/or digital marketing agencies

Preferred

• Experience using and/ or developing and executing go-to-market strategies for AI-enabled products
• Experience in similar categories of Talent Management/ Learning space
• Bachelor’s degree in Marketing, Business, Communications, or related field (MBA a plus)

We are committed to equal pay for equal work and believe in compensation transparency. All salary ranges are standardized nationwide and will not vary by region. This role offers a competitive total compensation package, including a base salary of $125,000-$150,000 PLUS variable (bonus) compensation eligibility and stock options. Compensation offered will be based on a combination of factors such as experience, competencies, and internal equity.

Posting Date: March 6, 2026
*This role will stay open for a minimum of 3 days. 

Guild is hiring a Senior Product Analytics Data Scientist. 

The Opportunity

Guild's product organization is at an inflection point—and we need a data scientist who can ensure we're building the right things, measuring what matters, and proving impact. As our Senior Product Analytics Data Scientist, you'll be the strategic analytics partner for Grow Core and Payments Network, with expanding scope into Academy and Navigator. Your work will directly shape product strategy by ensuring leaders have the insights they need to focus investments on high-return solutions, validate that launches actually drive impact, and create objective accountability across the business. Without this role, our product and engineering efforts risk operating without understanding how our work affects members and the bottom line. This is your chance to change that.

Here are the outcomes you will be expected to achieve:

• Focus product investments on the highest-return solutions by providing actionable insights that inform roadmap prioritization
• Validate that product launches actually drive impact through rigorous experimentation and causal inference
• Create objective measures of accountability by defining and operationalizing KPIs that align business and mission incentives
• Enable a self-sufficient, data-driven product culture where leaders can access the insights they need without bottlenecks

Here's what you will do in this role to achieve these outcomes:

• Proactively influence product strategy and roadmap decisions through narrative insights and recommendations
• Define logical KPI driver trees in partnership with Senior Directors of Product Management that drive aligned incentives
• Own and lead analytical standards for the product organization—driving rigor across experimentation, causal inference, and descriptive analytics using Optimizely, Segment, and Fullstory
• Deliver dashboards and workflows that consistently provide value, articulate performance, and support prioritization decisions
• Consult with stakeholders on the feasibility and scope of reporting requests, enabling self-service whenever possible
• Translate ambiguous questions into concrete analysis with clear narratives for non-technical audiences
• Manipulate and analyze complex datasets using Snowflake, dbt, Databricks, and Looker/Omni
• Partner with Data Engineering to flag data quality issues, request new events/metrics, and define data requirements for existing and new products

You are probably a strong candidate for this role if you've accomplished:

• Partnered directly with product leaders to define KPIs and measurement frameworks that shaped roadmap decisions
• Designed and analyzed A/B tests or other causal inference methods that validated (or invalidated) product bets
• Built dashboards or reporting infrastructure that product teams actually used for ongoing decision-making—not one-off analyses
• Translated messy, ambiguous business questions into structured analyses with clear, actionable takeaways
• Identified data quality issues or gaps and worked cross-functionally to resolve them

Here are the skills/competencies you have that will be needed to achieve the expected outcomes:

• Strong proficiency in SQL and experience with modern data tools (Snowflake, dbt, Databricks, Looker or similar)
• Expertise in experimentation design, causal inference, and statistical rigor
• Ability to define meaningful KPIs and connect them to business outcomes through logical frameworks
• Experience with product analytics tooling (Optimizely, Segment, Fullstory, Amplitude, or similar)
• Strong communication skills—able to craft clear narratives for non-technical stakeholders
• Consultative mindset: you scope requests, push back when needed, and deliver what stakeholders actually need
• Comfort with ambiguity and the ability to structure problems independently

We are committed to equal pay for equal work and believe in compensation transparency. All salary ranges are standardized nationwide and will not vary by region. This role offers a competitive total compensation package, including a base salary of $120,000 - $140,000 and stock options. Compensation offered will be based on a combination of factors such as experience, competencies, and internal equity.

Posting Date: January 27, 2026

*This role will stay open for a minimum of 3 days. 

Guild is seeking a Senior Software Engineer to build scalable, reliable systems that empower our Employer Partners to administer education benefits and integrate employee data with Guild’s platform. You’ll play a pivotal role in developing tools and services that streamline eligibility processing, policy management, and data onboarding—ensuring employees get the most out of Guild’s career opportunity programs.

This role is ideal for product-minded engineers who are excited by cross-functional collaboration, thrive in a modern AWS serverless environment, and enjoy solving data and systems design challenges at scale.

As a Senior Software Engineer, you will:

• Design and build robust, scalable systems that power data onboarding, eligibility workflows, and benefit policy administration.
• Develop backend services, APIs, ETL pipelines, and internal tools using serverless architecture (AWS Lambda, Glue, S3, API Gateway).
• Create clean, testable, maintainable code in TypeScript/Node.js and Python following best practices and established patterns.
• Ensure system observability, security, and performance using tools like Datadog and CloudWatch.
• Collaborate closely with engineers, product managers, designers, internal ops, and customer technical teams to deliver high-impact features.
• Write and maintain comprehensive tests (unit, contract, BDD, and end-to-end) and support CI/CD pipelines for consistent delivery.
• Participate in Agile ceremonies and on-call rotations, with a focus on production readiness, system health, and issue resolution.
• Contribute to system architecture decisions, technical documentation, and mentoring of junior developers.
  
  

You are a strong fit if you have:

• 5+ Years Hands-on Experience with: TypeScript/Node.js, Python, React, PostgreSQL, DynamoDB, GraphQL, REST APIs.
• Experience with AWS tools: Lambda, Glue, API Gateway, S3, EventBridge, SQS, Secrets Manager, CDK, Serverless Framework.
• Knowledge of: ETL pipeline development, CSV/API data ingestion, data transformation, event-driven architecture.
• Testing & Tooling: Jest, Pact, Cypress, Gherkin, CI/CD pipelines, infrastructure as code (AWS CDK/CloudFormation).
• AI Experience: Experience integrating LLM APIs (e.g., OpenAI) and building AI-powered features such as virtual assistants, summarization tools, vector search, or retrieval-augmented generation (RAG) workflows. Proficient in using AI-assisted development tools (e.g., GitHub Copilot, Cursor) with a solid understanding of their application in production-grade environments.
• Strong communication, collaboration, and documentation skills.
• Ability to balance technical decisions with business goals and deliver pragmatic solutions.
• A passion for Guild’s mission to unlock opportunity through education and upskilling.

We are committed to equal pay for equal work and believe in compensation transparency. This role offers a competitive total compensation package, including a base salary of $150,000 - $180,000, and stock options. Compensation offered will be based on a combination of factors such as experience, competencies, and internal equity.

Posting Date: September 9th, 2025
*This role will stay open for a minimum of 3 days.