Now Hiring - The Medicare Basics - Director of Property & Casualty Auto Insurance Sales in Clearwater, FL

Full description of the position

Launch & Scale a New Auto Insurance Division Location: In Person - Clearwater, Florida (Required) Reports to: Executive Leadership Compensation: Competitive base + performance based incentive + long term upside About the Company We are a tech forward, multi line insurance agency and financial services platform serving 300,000+ legacy customers nationwide. The organization operates across health, benefits, and financial products and is now expanding aggressively into Property & Casualty, beginning with Auto Insurance. This is not a maintenance role. This is a build, launch, and own opportunity within a technology enabled organization with real distribution, real data, and real scale. The Opportunity We are seeking a Director of Property & Casualty Auto Insurance Sales to create and lead a new Auto Insurance division from the ground up. This role owns strategy, execution, and results, including carrier partnerships, sales buildout, and monetization of an existing 300k+ customer base. This position is fully in person at the Clearwater office and works directly with executive leadership, product, marketing, and technology teams. What You Will Do * Launch a new Auto Insurance division from zero to scale * Design and execute the go to market strategy for selling auto insurance to 300k+ existing customers * Select, negotiate, and manage carrier partnerships and appointments * Build sales infrastructure including workflows, scripts, pricing strategy, and compliance * Leverage technology, data, and automation to drive conversion and efficiency * Hire, train, and manage sales leadership, agents, and operational support * Integrate Auto offerings into a broader multi line insurance ecosystem * Own revenue targets, conversion metrics, CAC, retention, and profitability * Establish forecasting, reporting, and performance dashboards * Operate day to day from the Clearwater office, setting culture, pace, and accountability Who You Are * Proven leader with deep experience in Property & Casualty Auto insurance sales * Demonstrated success building or scaling an insurance sales organization * Strong command of carrier economics, commissions, underwriting, and compliance * Experience monetizing large customer bases, inbound demand, or cross sell channels * Comfortable operating in a tech enabled, data driven environment * Execution focused, commercially sharp, and accountable * Licensed or licensable in required states * Willing and able to work in person in Clearwater, Florida What Makes This Role Different * Immediate access to 300,000+ existing customers * Greenfield ownership of a new revenue division * Technology and data already in place to scale quickly * Executive level visibility and influence * Ability to shape strategy, structure, and team from day one * Significant upside tied directly to performance Why This Role * Rare opportunity to build a P&C Auto division from scratch * Strong leadership commitment and capital support * Real distribution without startup risk * Opportunity to create long term value and career defining impact Job Types: Full-time, Permanent Pay: $125,000.00 - $155,000.00 per year Benefits: * Dental insurance * Health insurance * Paid time off * Vision insurance Application Question(s): * Have you built or scaled an Auto insurance sales organization (not just managed a steady-state book)? * Have you led carrier relationships for Auto (appointments, compensation schedules, underwriting guidelines, compliance)? * Do you have 5+ years of experience in Property & Casualty insurance with a focus on Auto? * What's the largest sales team you've built or led in Auto (agents/ICs/SDRs)? License/Certification: * 2-20 (Preferred) Work Location: In person