Regional Sales Manager, Large Group Plans (Houston) - Sidecar Health

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