Regional Sales Manager, Broker Sales (Tampa)

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.
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, within your 40% travel footprint
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 or ability to obtain one quickly
Nice to have
Experience at a general agency such as BenefitMall or a regional benefits distributor, 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.
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.