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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
Sidecar Health is an Equal Opportunity employer committed to building a diverse team. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status or disability status.
What you need to know about the Boston Tech Scene
Boston is a powerhouse for technology innovation thanks to world-class research universities like MIT and Harvard and a robust pipeline of venture capital investment. Host to the first telephone call and one of the first general-purpose computers ever put into use, Boston is now a hub for biotechnology, robotics and artificial intelligence — though it’s also home to several B2B software giants. So it’s no surprise that the city consistently ranks among the greatest startup ecosystems in the world.
Key Facts About Boston Tech
- Number of Tech Workers: 269,000; 9.4% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: Thermo Fisher Scientific, Toast, Klaviyo, HubSpot, DraftKings
- Key Industries: Artificial intelligence, biotechnology, robotics, software, aerospace
- Funding Landscape: $15.7 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Summit Partners, Volition Capital, Bain Capital Ventures, MassVentures, Highland Capital Partners
- Research Centers and Universities: MIT, Harvard University, Boston College, Tufts University, Boston University, Northeastern University, Smithsonian Astrophysical Observatory, National Bureau of Economic Research, Broad Institute, Lowell Center for Space Science & Technology, National Emerging Infectious Diseases Laboratories
