Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and accessible for everyone. We know that to accomplish this lofty mission, we need driven people who will make things happen.

The passionate people who make up Sidecar Health’s team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent.

If you want to use your talents to transform healthcare in the United States, come join us!

About the Role

As an Sales Development Representative at Sidecar Health, you are the first reason an employer believes we're different - showing up with curiosity, energy, and a product that's genuinely worth getting excited about! We're reimagining how employers and their members experience healthcare, and that's a story worth telling.

This role is for someone who is passionate about the mission, thrives in a performance-driven environment, and wants to grow alongside a product that's changing lives.

What You’ll Do

• Prospect into target accounts through outbound calls, emails, LinkedIn outreach, and multi-touch sequences
• Hit daily and weekly activity expectations with consistency and urgency
• Conduct light discovery to qualify interest, fit, and buying readiness
• Book high-quality meetings that convert into real opportunities for our sales team
• Maintain clean data in Salesforce and follow the SDR playbook for messaging and sequencing
• Collaborate with Regional Sales Managers and the SDR Manager to refine outreach, improve conversion rates, and share learnings
• Bring energy and ownership — participate in call coaching, team huddles, and skill-building sessions
• Represent Sidecar Health with credibility, clarity, and a member-first mindset
• Deliver results: consistent meeting attainment, strong conversion quality, clean operational execution, and week-over-week improvement

What You'll Bring

• 1+ year of experience in an outbound SDR/BDR role or similar high-volume prospecting environment
• Strong communication skills and comfort reaching out to prospects through multiple channels
• Ability to manage structured daily activity while staying organized and resilient
• Familiarity with Salesforce, Outreach, and LinkedIn Navigator (or willingness to learn quickly)
• A growth mindset — coachable, driven, and committed to improving each week
• Track record (or clear potential) for hitting meeting goals, converting qualified leads, and contributing to pipeline
• Professional presence, attention to detail, and a genuine desire to build a career in sales

What You'll Get

• Competitive base salary ($60,000) with uncapped performance-based commission and equity
• Comprehensive Medical, Dental, and Vision benefits 
• A 401k retirement plan 
• Paid vacation and company holidays 
• Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S. 

Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and accessible for everyone. We know that to accomplish this lofty mission, we need driven people who will make things happen.

The passionate people who make up Sidecar Health’s team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent.

If you want to use your talents to transform healthcare in the United States, come join us!

About the Role

Our Member Care team is at the forefront of our business. Their role is easily the most important: supporting our members on their healthcare journeys. We're growing our team and looking for warm, passionate people to join us and help deliver the best experience in healthcare. Your job will be to help our members - to answer their questions, help them solve problems, and ensure they have access to the care they need. As a startup, there is no shortage of opportunities, responsibilities, and growth! You'll work alongside a dynamic team that is disrupting the healthcare industry and having a positive and meaningful impact on our members' lives every day. 

Job Responsibilities

• Handle inbound calls and chat boxes from our members in regard to Sidecar Health’s products and services 

• Provide excellent customer service in a timely and positive manner 

• Build rapport and maintain positive relationships with existing members to understand their needs and ensure a memorable member experience  

• Handle issues and complaints where appropriate  

• Maintain policies and standard operation procedures 

 Requirements

• Adaptable and resilient - you thrive in a fast-moving, ever-changing startup environment

• People-first communicator - you listen with empathy, connect easily, and meet members where they are

• Clear and confident in both written and spoken communication, with the ability to answer questions in the moment

• Detail-oriented problem solver - you spot the small things and think creatively to help members navigate their plans

• Education: High school diploma or equivalent required; bachelor’s degree preferred

• Bilingual in English and Spanish (preferred)

• Experience in healthcare or insurance (preferred)

• Available for one or more of these shifts options (Eastern Standard Time):

  • Monday–Friday: 10:00 AM – 6:30 PM

  • Monday–Friday: 11:00 AM – 7:30 PM

  • Monday–Friday: 11:30 AM – 8:00 PM

  • Monday–Friday: 8:00 AM - 12:00 PM and 4:00 PM - 8:00 PM

  • Saturday–Sunday: 9:00 AM – 5:00 PM and Monday–Wednesday: 10:30 AM -7:00 PM (Off Thursday & Friday)

What You'll Get 

• Competitive hourly wage ($19.00) 
• Fully paid Sidecar Health medical, dental, and vision - coverage for you and your whole family, on us
• A 401k retirement plan
• Paid vacation and company holidays
• Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S.

Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and accessible for everyone. We know that to accomplish this lofty mission, we need driven people who will make things happen.

The passionate people who make up Sidecar Health’s team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent.

If you want to use your talents to transform healthcare in the United States, come join us!

About the Role

This is a high-impact individual contributor role on our platform team, building large-scale data pipelines and distributed systems that power Sidecar Health's core product. You'll take full ownership of complex, ambiguous problems from architecture through production — designing, shipping, and running the systems you build. If you're a strong senior engineer who thrives on end-to-end ownership and wants your work to matter in healthcare, this is the role for you.

**MUST BE BASED IN CALIFORNIA**

What You'll Do 

• Design and own high-throughput, distributed data pipelines and platform infrastructure from concept through production
• Decompose large, ambiguous initiatives into structured, executable plans that the team can move on in parallel
• Write production-grade Python — strongly typed, well-structured, and built to last — not scripts or notebooks
• Optimize SQL at scale: query tuning, data modeling, and understanding execution plans
• Architect across boundaries — defining contracts between frontend, backend services, and infrastructure
• Be a technical resource and mentor for junior engineers, and partner directly with leadership on roadmap and technical decisions
• Instrument systems for observability — knowing what to monitor, not just how to read a dashboard

What You'll Bring 

• 5+ years of professional software engineering experience with full ownership of production systems
• Strong proficiency in Python (mypy, Pydantic, proper abstractions) and SQL at scale
• Deep experience building and operating distributed data pipelines and event-driven architectures
• Hands-on AWS experience: Lambda, SQS, IAM, CloudWatch, and cost-aware design
• Docker as a first-class practice
• Habitual, fluent use of AI tools (Claude, Cursor, etc.) as part of your daily workflow
• Observability experience with Datadog or equivalent
• Familiarity with FastAPI, Django, SQLAlchemy, Celery, or Infrastructure-as-Code (Terraform, CDK) is a strong plus
• Bachelor's or Master's degree in Computer Science, Information Systems, or a related field

The Reality

This is a startup. We move fast. We prioritize impact over polish. We expect:

• Bias for action — ship, learn, iterate
• Ownership — you design it, build it, run it
• Pragmatism — solve real problems, not theoretical ones
• Resilience — ambiguity comes with the territory

Healthcare is complex and broken. The work matters.

What You'll Get 

• Competitive salary, bonus opportunity, and equity package  
• Comprehensive Medical, Dental, and Vision benefits
• A 401k retirement plan
• Paid vacation and company holidays
• Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S.

Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and accessible for everyone. We know that to accomplish this lofty mission, we need driven people who will make things happen.

The passionate people who make up Sidecar Health’s team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent.

If you want to use your talents to transform healthcare in the United States, come join us!

About the Role

This is a high-impact individual contributor role at the core of our backend engineering team, building the services, APIs, and data systems that power Sidecar Health's platform. You'll own complex, performance-critical systems end-to-end — from design through deployment — and make the architectural decisions that keep us fast and reliable as we scale. If you treat every feature like your name is on it and want to build things that matter in healthcare, this is the role for you.

**MUST BE BASED IN CALIFORNIA**

What You'll Do 

• Design, build, and own scalable backend services and APIs that handle complex healthcare data and workflows
• Optimize database queries and data models to ensure system performance and reliability at scale
• Evaluate and articulate technical tradeoffs across system design, performance, and maintainability
• Integrate AI tools and agentic coding patterns into backend workflows where they add real value
• Write clean, well-tested, production-grade code with a high bar for quality
• Partner with product, data, and cross-functional stakeholders to translate requirements into robust technical solutions
• Contribute to engineering standards through code reviews, technical discussion, and better defaults

What You'll Bring 

• 5+ years of professional software engineering experience with strong backend ownership of production systems
• Deep expertise in Java and/or Python
• Proven experience with system design and the ability to articulate tradeoffs between architectural approaches
• Solid fundamentals in testing, debugging, performance optimization, and code review
• Habitual, fluent use of AI tools (Claude, Cursor, etc.) as part of your daily workflow
• Comfortable owning cloud deployments, preferably on AWS (EC2, Lambda, RDS, S3)
• Experience with CI/CD pipelines and DevOps practices
• Familiarity with data engineering frameworks — Airflow, dbt, Snowflake, or Dagster — is a strong plus
• Experience building AI agents is a plus
• Bachelor's degree in Computer Science or equivalent practical experience

The Reality

This is a startup. We move fast. We prioritize impact over polish. We expect:

• Bias for action — ship, learn, iterate
• Ownership — you design it, build it, run it
• Pragmatism — solve real problems, not theoretical ones
• Resilience — ambiguity comes with the territory

Healthcare is complex and broken. The work matters.

What You'll Get 

• Competitive salary, bonus opportunity, and equity package  
• Comprehensive Medical, Dental, and Vision benefits
• A 401k retirement plan
• Paid vacation and company holidays
• Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S.

Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and accessible for everyone. We know that to accomplish this lofty mission, we need driven people who will make things happen.

The passionate people who make up Sidecar Health’s team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent.

If you want to use your talents to transform healthcare in the United States, come join us!

About the Role

This is a high-impact individual contributor role where you'll own the full product experience — from the APIs that power our platform to the interfaces our members interact with every day. You'll work directly with product and design to ship features that make healthcare more accessible, and you'll use AI tools as a core part of how you build. If you move fast, care deeply about craft, and want your work to matter, this is the role for you.

**MUST BE BASED IN CALIFORNIA**

What You'll Do 

• Build and ship full-stack features end-to-end, from backend APIs to polished member-facing UI
• Design scalable systems and make deliberate architectural tradeoffs between performance, maintainability, and speed to ship
• Integrate AI tools and LLM APIs into product workflows where they add real value
• Write clean, well-tested, production-grade code with a high bar for quality
• Partner with product, design, and stakeholders across the business to translate requirements into great software
• Contribute to engineering standards through code reviews, technical discussion, and better defaults

What You'll Bring 

• 5+ years of professional software engineering experience with full-stack ownership of production systems
• Deep expertise in JavaScript/TypeScript
• Strong React and Next.js experience building modern, responsive web applications
• Solid fundamentals in system design, testing, debugging, and code review
• Habitual, fluent use of AI tools (Claude, Cursor, etc.) as part of your daily workflow
• Comfortable owning cloud deployments, preferably on AWS
• Bachelor's degree in Computer Science or equivalent practical experience

The Reality

This is a startup. We move fast. We prioritize impact over polish. We expect:

• Bias for action — ship, learn, iterate
• Ownership — you design it, build it, run it
• Pragmatism — solve real problems, not theoretical ones
• Resilience — ambiguity comes with the territory

Healthcare is complex and broken. The work matters.

What You'll Get 

• Competitive salary, bonus opportunity, and equity package  
• Comprehensive Medical, Dental, and Vision benefits
• A 401k retirement plan
• Paid vacation and company holidays
• Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S.

Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and accessible for everyone. We know that to accomplish this lofty mission, we need driven people who will make things happen.

The passionate people who make up Sidecar Health’s team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent.

If you want to use your talents to transform healthcare in the United States, come join us!

About the Role

We're seeking for a Director of Quality and Continuous Improvement who can lead from both ends of the strategy-to-execution spectrum. The role is structured around two distinct functions: (1) overhauling how we approach quality assurance, leveraging AI and speech analytics to shift from manual, sample-based review to continuous, intelligent insights; and (2) converting those signals into action across the organization — whether through training, documentation and SOPs, or broader cross-functional process improvement.

The right person for this role thrives in both the strategic and tactical – presenting quality trends and risks to executive leadership while rolling up their sleeves to drive improvement initiatives from insight to implementation understanding what “good” looks like and how to build the systems, tools, and team to get there.

Key Responsibilities

Quality Strategy & AI Evolution (40%)

• Own the Quality evolution roadmap, including the transition from manual, sample-based evaluation to AI-powered scoring, automated coverage, and always-on quality insights
• Leverage AI, speech analytics, and interaction data to surface actionable coaching and process improvement opportunities
• Design and maintain quality scorecards, evaluation criteria, and calibration standards – leading sessions calibration sessions to ensure consistency across evaluators and time
• Perform deep-dive analysis on quality trends, complaints, and outliers, generating executive-level reports with actionable insights

Converting Insight into Action (30%)

• Design feedback loops connecting quality insight to action – whether that’s coaching, training updates, documentation changes, workflow updates, or technology needs
• Conduct structured root cause analysis on critical failures, escalations, and member complaint trends
• Build business cases for improvement initiatives with clear ROI projections and measurable impact
• Pilot and test new processes, workflows, and member interaction scripts before scaling; create and maintain SOPs and documentation standards

Team and Stakeholder Leadership (30%)

• Partner with the Member Services leadership team to define and execute a multi-year Quality Assurance and Continuous Improvement strategy aligned to company growth objectives
• Build, lead, and develop a team of QA analysts and continuous improvement practitioners including certification pathways, analyst development tracks, and Green/Black Belt mentorship
• Represent operational excellence in cross-functional forums, present findings, risks, and recommendations to executive leadership
• Champion a continuous improvement culture across Member Services, partnering with Operations, Technology, Product, Training, and Compliance on integrated initiatives
• Ensure compliance with healthcare regulations (HIPAA, CMS, state requirements), partner with Legal and Compliance teams on audit readiness, and lead corrective action plans

Required Qualifications

• 8-10 years of progressive experience in process excellence, quality management, or operational improvement, with 3-5 years in leadership roles
• Bachelor’s degree in business administration, Operations Management, Healthcare Administration, or related field
• Demonstrated application of methodology in a contact center or healthcare services environment
• Direct experience with quality monitoring, scorecards, contact center analytics, and coaching leaders with documented performance outcomes
• Hands-on experience directing or implementing AI-powered quality tools, speech analytics platforms, or automated scoring systems
• Demonstrated ability to translate quality analytics into business recommendations for executive audiences
• Understanding of healthcare regulations: HIPAA, ACA, CMS, and state insurance compliance requirements
• Strong executive presence with excellent facilitation, coaching, and communication skills across all organizational levels
• Analytical mindset with experience in statistical analysis and converting data into actionable operational decisions
• Bias toward action, rapid iteration, and an entrepreneurial approach to problem-solving

Preferred Qualifications

• Lean Six Sigma Green Belt or Black Belt strongly preferred
• Additional certifications in COPC, Project Management (PMP), or Change Management
• Experience in high-growth healthcare technology or insurtech with contact center operations background
• Familiarity with Genesys Cloud, or CRM-integrated quality tools

What You'll Get

• Competitive salary, bonus opportunity, and equity package 
• Comprehensive Medical, Dental, and Vision benefits 
• A 401k retirement plan 
• Paid vacation and company holidays 
• Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S. 

Sidecar Health adopts a market-based approach to compensation, where base pay varies depending on location and is further influenced by job-related skills and experience. 

Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and accessible for everyone. We know that to accomplish this lofty mission, we need driven people who will make things happen. 

The passionate people who make up Sidecar Health’s team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent. 

If you want to use your talents to transform healthcare in the United States, come join us!

About the Role

Sidecar Health is transforming how employers and their members experience healthcare — through transparent cash pricing, no provider networks, and meaningful cost savings. As we accelerate our enterprise growth, we are looking for a VP of Strategic Accounts to lead that charge. Reporting directly to the CEO, this individual will own our enterprise sales strategy and execution at a pivotal moment for the company, with a pipeline of national accounts already in active evaluation.

What You'll Do

• Develop and execute a comprehensive enterprise sales strategy to drive new business growth
• Set and achieve ambitious revenue targets, with a focus on net-new client acquisition
• Identify and pursue opportunities within jumbo and national employer groups
• Build and scale a repeatable, high-performing sales process
• Build and maintain strong relationships with brokers, consultants, and enterprise employer clients
• Partner with clients to understand their unique needs and work with internal teams to tailor solutions accordingly
• Serve as a trusted advisor on health plan solutions and benefits strategy
• Stay informed about industry trends, competitor offerings, and regulatory changes
• Collaborate with product and marketing teams to refine offerings based on market feedback and client insights
• Partner with finance, operations, and member experience teams to ensure seamless client onboarding and ongoing support
• Provide input on pricing strategies, service enhancements, and value propositions

What You'll Bring

• 10+ years of experience in health insurance or employee benefits sales, with a strong focus on jumbo/national employer groups
• Proven track record of securing enterprise clients and driving significant revenue growth
• Strong network within the broker/consultant community and with benefits leaders at large organizations
• Exceptional communication, negotiation, and relationship-building skills
• Deep understanding of health plan products, self-funded and ASO models, and benefits administration
• Strategic thinker with the ability to balance long-term vision and short-term execution
• Experience in a high-growth, entrepreneurial environment is a plus
• Bachelor's degree required

What You'll Get 

• Competitive salary, uncapped incentive bonus, and equity package   
• Comprehensive Medical, Dental, and Vision benefits 
• A 401k retirement plan 
• Paid vacation and company holidays 
• Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S. 

Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and attainable for everyone. We know that to accomplish this lofty mission, we need driven people who will make things happen.

The passionate people who make up Sidecar Health’s team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent.

If you want to use your talents to transform healthcare in the United States, come join us!

**Must reside in California for consideration**

About the Role

As a Lead Product Manager at Sidecar Health, you will own critical member-facing product areas and drive the strategy, development, and launch of innovative features that enable members to shop for care more effectively. You’ll lead complex initiatives that improve how members search for care, understand costs, and make informed healthcare decisions.

In this role, you will partner closely with engineering, design, and business leaders to define product vision, set roadmap priorities, and deliver high-impact solutions that improve member experience and drive company growth. You will operate with significant autonomy while helping shape product direction across teams.

What You'll Do 

• Lead product strategy and execution for key member-facing experiences that help members find high-quality, cost-effective care
• Define and own product roadmaps, aligning initiatives with company goals and member needs
• Drive discovery and ideation for new capabilities that improve healthcare shopping, transparency, and personalization
• Map and deeply understand member healthcare journeys to identify opportunities for product innovation
• Use data, experimentation, and user insights to inform product decisions and measure success
• Partner with engineering leaders to scope initiatives, define MVPs, and deliver high-quality solutions through Agile development
• Lead a cross-functional pod of engineers and designers to ship impactful product improvements
• Influence product direction across teams and collaborate with product leadership on longer-term platform strategy
• Establish strong product practices, documentation, and processes that improve team efficiency and execution

What You'll Bring 

• Bachelor’s or Master’s degree in Computer Science, Information Systems, Business Administration, or a related field
• 5+ years of experience in product management, with a focus on search engines or data analytics platforms
• Expertise in user-facing applications, with a strong sense of design and user experience
• Proficiency in SQL for independent data analysis and investigation
• Deep understanding of Agile development and Scrum methodology
• Strong analytical, troubleshooting, and problem-solving abilities
• Skill in breaking complex problems down into MVPs for faster implementation
• Ability to translate technical requirements for broad business audiences
• Talent for structuring and clarifying complex, ambiguous situations
• Experience working cross-functionally and influencing multiple stakeholders
• Experience in a fast-paced, growth-stage startup environment is a plus
• Excellent written and verbal communication skills
• Passion for a data-driven, results-oriented culture

What You'll Get 

• Competitive salary, bonus opportunity, and equity package  
• Comprehensive Medical, Dental, and Vision benefits
• A 401k retirement plan
• Paid vacation and company holidays
• Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S.

In taking a market-based approach to compensation, base pay may vary depending on location. Additionally, base pay may vary considerably depending on job-related skills and experience. The current expected salary range for this position is: $160,000 - $180,000. 

Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and accessible for everyone. We know that to accomplish this lofty mission, we need driven people who will make things happen.

The passionate people who make up Sidecar Health’s team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent.

If you want to use your talents to transform healthcare in the United States, come join us!

What You’ll Do

• Own and scale Sidecar Health’s broker growth strategy in your region - equipping brokers and GAs with the knowledge, tools, and confidence to win
• Build deep, trusted relationships with brokers, GAs, and distribution partners, becoming a go-to expert in your market
• Identifying high-potential distribution partners to invest in and grow with over time
• Serve as the face of Sidecar Health locally, representing us at broker events, industry meetings, and community gatherings
• Identify, test and refine new go-to-market and growth strategies, sharing insights to shape national sales efforts
• Consistently meet or exceed sales goals while delivering an exceptional partner experience
• Bring competitive intelligence and market insights to inform product and strategy decisions

What You’ll Bring

• 4+ years of sales experience within healthcare, benefits, or adjacent industries such as PBM, ancillary benefits, stop-loss, PEO, payroll, dental, vision, or B2B software
• Experience calling on brokers and/or agencies preferred, but not required
• Bachelor’s degree 
• Proven ability to generate and develop new opportunities, including self-sourced leads, without relying on pre-existing broker networks
• Strong relationship-building and influencing skills in a consultative, trust-based sales environment
• Track record of meeting or exceeding growth or revenue goals
• Experience using market data and competitive insights to prioritize efforts and improve performance
• Comfort with targeted outreach, networking, and in-market presence—prioritizing long-term partnerships over high-volume call activity
• Willingness to travel up to 40% within Texas to build and deepen regional relationships

What You'll Get

• Competitive base salary with uncapped performance-based commission and equity
• Comprehensive Medical, Dental, and Vision benefits
• 401(k) retirement plan
• Paid time off and company holidays
• Clear opportunity to build, own, and grow a book of business at a fast-scaling company redefining healthcare insurance in the U.S.
• A seat at the table in shaping how Sidecar Health goes to market as we scale