Regional Sales Manager – Broker Sales

Sidecar Health

. Own broker relationships across a territory spanning Tampa to Naples and Lakeland .

Posted 10/23/2026full-timeRemote • Florida • United StatesMid-LevelSeniorWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates strong relationship management skills with established broker and consultant connections in the Tampa Bay market, alongside deep fluency in self-funded and level-funded plan design. Proven ability to develop tailored proposals and manage employer group opportunities effectively.

Highest-signal resume keywords

Established Broker RelationshipsGroup Benefits Channel SalesSelf-Funded Plan DesignFlorida Life And Health LicenseEmployer Group Management

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills

Group Benefits SalesPlan DesignProposal DevelopmentPipeline ManagementCase Management

Soft Skills

Relationship-First Sales StyleTrust-Building

Certifications & Qualifications

Florida Life And Health License

Industry Keywords

Broker RelationshipsGeneral AgencyRegional BrokerageEmployer GroupsBenefit Amount Concept

About the role

Key responsibilities & impact

Own broker relationships across a territory spanning Tampa to Naples and Lakeland
Map existing broker and consultant relationships and identify the 20 who can move business in the next 90 days
Learn how the Benefit Amount model works and 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
Qualify and prioritize 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
Build a repeatable pipeline cadence across the full territory, with a 40% travel footprint

Requirements

What you’ll need

Established broker and consultant relationships in the Tampa Bay market that you could activate this week
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
Ability to explain why legacy insurance leaves money on the table for employers and employees
Relationship-first sales style
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
Nice to have: Familiarity with presenting the Benefit Amount concept to brokers and employer HR or CFO audiences
Nice to have: Exposure to employer groups ranging from 100 to 2,000 lives and ability to manage cases start to finish
Nice to have: History of finishing at or near the top of a regional leaderboard in a broker-distributed benefits product

Benefits

Comp & perks

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; choice of 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
401(k) retirement plan
Paid vacation, company holidays, and paid parental leave
$50 a month toward internet and $50 a month toward phone, reimbursed through expenses
Opportunity to make an impact at a rapidly growing, mission-driven company transforming healthcare in the U.S.