Regional Sales Manager – Broker Sales

This is a fully remote position, open to applicants in Florida.

📋 Description

• Manage broker relationships throughout a territory that includes Tampa, Naples, and Lakeland.

• Analyze current broker and consultant connections to pinpoint the top 20 who can drive business within the next 90 days.

• Understand the Benefit Amount model and effectively position it against traditional insurance during broker discussions.

• Establish a consistent presence in the broker community of Tampa, St. Petersburg, and Clearwater through various meetings, events, and casual interactions.

• Evaluate and prioritize employer group opportunities within the 100–2,000 employee range identified by broker partners.

• Strengthen connections with general agencies and regional brokerages to ensure Sidecar becomes the go-to recommendation during renewals.

• Collaborate with underwriting and product teams to create competitive proposals customized for employer groups.

• Develop a consistent pipeline strategy across the entire territory, requiring 40% travel.

⛳️ Requirements

• Established connections with brokers and consultants in the Tampa Bay area that can be activated immediately.

• A minimum of 5 years in group benefits channel sales—whether on the carrier, GA, or TPA side—with a foundation built on trust, not just transaction volume.

• Strong understanding of self-funded or level-funded plan design.

• Capability to articulate why traditional insurance can result in financial losses for employers and employees.

• A relationship-first approach to sales.

• Active Florida Life and Health license or the ability to obtain one swiftly.

• Preferred: Experience with a general agency like BenefitMall or a regional benefits distributor.

• Preferred: Experience presenting the Benefit Amount concept to brokers and HR or CFO representatives of employers.

• Preferred: Background working with employer groups between 100 and 2,000 lives, with the ability to manage cases from start to finish.

• Preferred: Proven track record of ranking 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 available from day one, with Sidecar covering 100% of the premium for you and your dependents; options include an HSA-eligible plan or a $0 deductible plan.

• Dental and vision coverage from the first day, with Sidecar covering 100% of your premium and 80% for your dependents.

• 401(k) retirement plan.

• Paid vacation, company holidays, and paid parental leave.

• $50 monthly reimbursement for internet and $50 monthly for phone expenses.

• Opportunity to make a significant impact in a rapidly growing, mission-driven company that is transforming healthcare in the U.S.