Regional Sales Manager, Broker Sales

Job overview

The Regional Sales Manager, Broker Sales role is based in Tampa, FL, and covers a territory from Tampa to Naples and Lakeland. Compensation is described as a competitive base salary with uncapped performance-based commission and equity; numeric pay is not specified. Sidecar Health’s mission is to make excellent healthcare affordable and accessible. The manager builds broker and consultant relationships, develops a territory pipeline, and qualifies employer-group opportunities. The role works with internal sales, underwriting, and product teams to position proposals and expand access to Sidecar Health’s insurance offering.

What you'll do

• Map broker and consultant relationships across the territory
• meet with sales leadership and internal teams to understand and position the Benefit Amount model
• establish a presence in Tampa, St. Petersburg, and Clearwater broker communities
• qualify employer-group opportunities
• deepen relationships with agencies and brokerages
• collaborate with underwriting and product teams on proposals
• build a repeatable pipeline cadence across the territory.

What we're looking for

Skills & competencies

regional sales manager

broker sales

full-time

tampa fl

tampa-to-naples territory

lakeland

health insurance

broker relationships

group benefits

40% travel

uncapped commission

equity package

Work arrangement

• Weekend coverage required

Benefits & perks

• Medical coverage from day one, dental and vision coverage, 401(k), paid vacation, company holidays, paid parental leave, and monthly internet and phone reimbursements.

Why this role

The role requires approximately 40% travel, established Tampa Bay broker relationships, five or more years of group benefits channel sales experience, and an active Florida Life and Health license or ability to obtain one quickly.

About the employer

Sidecar Health is hiring for this role. Industry: Insurance Agencies and Brokerages. Sector: 52.