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