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 looking for a Regional Sales Manager based in Tampa, FL to own broker relationships across a territory spanning Tampa to Naples and Lakeland. This is a channel sales role — your job is to be so embedded in the local broker community that Sidecar is the first call brokers make when a client is frustrated with their legacy insurance bill or heading into renewal. You won't knock on employer doors; you'll build the trust with brokers and consultants that makes the business come to you.

*Must be comfortable with up to 40% travel across the Tampa Bay to Naples area *

What You’ll Do

• Map your existing broker and consultant relationships across the Tampa Bay to Naples corridor and identify the 20 who can move business in the next 90 days
• Meet with Sidecar's sales leadership and internal teams to understand how the Benefit Amount model works and how to position it against legacy insurance in broker conversations
• Establish a regular presence in the Tampa, St. Petersburg, and Clearwater broker community through meetings, events, and informal touchpoints
• Begin qualifying and prioritizing employer group opportunities in the 100–2,000 employee range surfaced through broker partners
• Deepen relationships with general agencies and regional brokerages so Sidecar becomes a default recommendation at renewal
• Collaborate with underwriting and product teams to develop competitive proposals tailored to employer groups whose members want more choice and the ability to get money back
• Build a repeatable pipeline cadence across the full territory, covering Tampa north to Lakeland and south to Naples

What You Bring

• Established broker and consultant relationships in the Tampa Bay market that you could activate this week, not someday
• 5 or more years in group benefits channel sales — carrier, GA, or TPA side — with a track record built on trust rather than transaction volume
• Deep fluency in self-funded or level-funded plan design and the ability to explain why legacy insurance leaves money on the table for employers and their employees
• A relationship-first sales style: brokers call you with problems, you don't have to chase them for meetings
• Active Florida Life and Health license

Nice to have

• Experience in a role where broker distribution was the core of your daily work 
• Familiarity with presenting the Benefit Amount concept — fixed, transparent reimbursement tied to local cost of care — to brokers and employer HR or CFO audiences
• Exposure to employer groups ranging from 100 to 2,000 lives with demonstrated ability to manage cases start to finish
• History of finishing at or near the top of a regional leaderboard in a broker-distributed benefits product

What You’ll Get

• Competitive base salary with uncapped performance-based commission and an equity package
• Medical coverage from day one, with 100% of the premium paid by Sidecar for you and your dependents. Choose an HSA-eligible plan or a $0 deductible plan
• Dental and vision coverage from day one, with 100% of your premium covered, and 80% covered for your dependents
• A 401(k) retirement plan
• Paid vacation, company holidays, and paid parental leave
• Stay connected: $50 a month toward your internet and $50 a month toward your phone, reimbursed through expenses
• The opportunity to make an impact at a rapidly growing, mission-driven company transforming healthcare in the U.S.