Regional Sales Manager – Broker Sales

Job not on LinkedIn

🔥 3 minutes ago

🐊 Florida – Remote

🐊 Florida – Remote

⏰ Full Time

🟡 Mid-level

🟠 Senior

🤑 Sales

🦅 H1B Visa Sponsor

This company has sponsored H1B visas in the past.

👻 Ghost score 10%

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Sidecar Health

WebsiteLinkedInAll Job Openings

201 - 500 employees

Founded 2018

🏥 Healthcare

💼 Consulting

🛡️ Insurance

Healthcare • Consulting • Insurance

Sidecar Health is a health insurance company that provides comprehensive major medical insurance with upfront pricing and no network restrictions or referral requirements. Their goal is to put employees in control of their healthcare by giving them a clear budget for care and allowing them to choose any doctor without surprise costs. They emphasize access to prescriptions without limitations and protection for unplanned care. Sidecar Health also offers transparent pricing and the option for members to save money if they find providers who charge less than their plan pays. Their offerings include individualized access plans and employer plans, ensuring members always have a choice of qualified doctors.

📋 Description

• 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

• 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

• 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.