Sidecar Health - Regional Sales Manager, Broker Sales (Tampa)
Requirements
• 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 • 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 • 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.
Responsibilities
• 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
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