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Sidecar Health is transforming health insurance by making excellent healthcare affordable and accessible. The company is seeking 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 focused on building deep trust with brokers and consultants in the local community. Rather than direct employer outreach, you'll become so embedded in the broker ecosystem that Sidecar is the first call brokers make when clients are frustrated with legacy insurance or approaching renewal.
Key responsibilities include:
- Mapping existing broker and consultant relationships across the Tampa Bay to Naples corridor and identifying the 20 most capable of moving business within 90 days
- Meeting with Sidecar's sales leadership and internal teams to understand the Benefit Amount model and positioning against legacy insurance
- Establishing regular presence in Tampa, St. Petersburg, and Clearwater broker communities through meetings, events, and touchpoints
- Qualifying and prioritizing employer group opportunities in the 100–2,000 employee range surfaced through broker partners
- Deepening relationships with general agencies and regional brokerages to make Sidecar a default recommendation at renewal
- Collaborating with underwriting and product teams to develop competitive proposals tailored to employer groups
- Building a repeatable pipeline cadence across the full territory with a 40% travel footprint
The role offers competitive base salary with uncapped performance-based commission and equity package. Benefits include 100% premium coverage for medical, dental, and vision for employee and dependents, 401(k), paid vacation and parental leave, and $50/month internet and phone reimbursement.
Requirements:
- Established broker and consultant relationships in the Tampa Bay market that can be activated immediately
- 5+ 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 ability to explain why legacy insurance leaves money on the table
- Relationship-first sales style where brokers proactively call you with problems
- Active Florida Life and Health license or ability to obtain one quickly
Nice to have:
- Experience at a general agency such as BenefitMall or regional benefits distributor
- Familiarity with presenting the Benefit Amount concept to brokers and employer audiences
- Exposure to employer groups ranging from 100 to 2,000 lives with demonstrated case management ability
- History of finishing at or near the top of a regional leaderboard in broker-distributed benefits products
