True Captive

About True Captive

True Captive Insurance is a national medical stop-loss captive serving employers with 50–1,000 employees. We believe in healthcare that’s personal and insurance that isn’t complicated.

Through a full-service suite that includes TPA placement, reinsurance coordination, powerful healthcare analytics, and consultative support for employers and their employees, we help groups take control of their healthcare plans and costs — often creating a level of expense visibility and engagement that doesn’t exist in traditional insurance models.

We’re passionate about making insurance simpler, more transparent, and more aligned with employer goals. We work with brokers, advisors, and member companies to deliver better healthcare outcomes and smarter insurance performance.

About the Role

We’re looking for a dynamic Sales Leader to help expand our national footprint and bring more employers into our captive community. You’ll lead sales strategy, manage and grow the sales team, and build strong partnerships with innovative companies and brokers who are ready to rethink their health plans.

You’ll thrive in this role if you're entrepreneurial, consultative, and energized by changing the way people think about insurance.

Key Responsibilities

• Lead and execute a national sales strategy to drive new captive membership.
• Cultivate and manage relationships with benefits consultants, brokers, and TPAs.
• Identify and pursue opportunities with employers seeking to self-fund or explore alternative funding models.
• Educate prospects and partners on the value of captives, True Captive’s model, and our member-first approach.
• Collaborate cross-functionally with underwriting, marketing, operations, and leadership to drive growth goals.
• Represent True Captive at industry conferences, webinars, and networking events.
• Manage, mentor, and support the existing sales team to ensure accountability, professional development, and alignment with company goals.
• Build a scalable sales infrastructure to support continued national growth.

What We’re Looking For

• 5+ years of experience in health insurance, benefits consulting, stop-loss, or captive sales.
• Strong understanding of self-funding, TPAs, and the broker landscape.
• Proven track record of consultative sales success.
• Confident communicator and relationship builder with executive presence.
• Mission-driven mindset: You’re passionate about transforming health insurance.
• Self-starter who thrives in a fast-growing, entrepreneurial environment.

Why True Captive?

• Join a team that’s not just selling insurance — we’re reimagining it.
• Work alongside people who care deeply about making healthcare better.
• Competitive compensation, performance incentives, and long-term growth potential.
• A culture that values innovation, autonomy, and integrity.

Let’s change the way companies think about insurance — together.