Regional Sales Manager, Broker Sales (Tampa)

The role

The Regional Sales Manager will own broker relationships across a territory from Tampa to Naples and Lakeland. This channel sales role focuses on building trust with brokers and consultants to drive business.

What you will do

• Map existing broker and consultant relationships across the Tampa Bay to Naples corridor
• Meet with sales leadership and internal teams to understand the Benefit Amount model
• Establish a regular presence in the Tampa, St. Petersburg, and Clearwater broker community
• Qualify and prioritize employer group opportunities in the 100–2,000 employee range
• Deepen relationships with general agencies and regional brokerages
• Collaborate with underwriting and product teams to develop competitive proposals
• Build a repeatable pipeline cadence across the full territory

Required qualifications

• Established broker and consultant relationships in the Tampa Bay market
• 5 or more years in group benefits channel sales
• Deep fluency in self-funded or level-funded plan design
• 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 to brokers or employer HR or CFO audiences
• Exposure to employer groups ranging from 100 to 2,000 lives
• History of finishing at or near the top of a regional leaderboard in a broker-distributed benefits product

Benefits

• 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
• $50 a month toward your internet and $50 a month toward your phone, reimbursed through expenses

About the company

Sidecar Health is redefining health insurance with a mission to make excellent healthcare affordable and accessible for everyone. The team includes tech leaders, policy makers, and healthcare professionals looking to fix a broken system.