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Join the Inaugural Class of Roundstone Captive Academy

Roundstone Captive Academy is a hands-on experience for growth-minded producers ready to break out of the benefits status quo. Master one of the industry’s most powerful funding strategies and accelerate your career.

RCA_2025_Logo

Join the Inaugural Class of Roundstone Captive Academy

Roundstone Captive Academy is a hands-on experience for growth-minded producers ready to break out of the benefits status quo. Master one of the industry’s most powerful funding strategies and accelerate your career.

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Stand Out from the Crowd

With roughly 12 million commercial members leaving their current plans by 2030 for more innovative alternatives — you’re getting a serious advantage in a competitive market. From understanding how the model works to navigating conversations with CFOs, we’ll equip you with the real-world insights and tools to confidently lead with a smarter self-funded option.

Why Attend?

This isn’t your average insurance workshop. It’s built for advisors and account managers like you—ambitious, curious, and ready to win.

Network with top producers

Engage directly with Roundstone's experts

Leave with a game-changing differentiator

What to Expect

What’s Included:

First Day

Tuesday, August 12

4:30 PM - 6:00 PM

Check-in at Fidelity Hotel

6:00 PM – 6:20 PM

Meet in lobby & head to Guardians Game

6:40 PM – 9:00 PM

Game & Dinner with Roundstone Team

Second Day

Wednesday, August 13

7:00 AM – 8:15 AM

Breakfast

8:15 AM – 8:50 AM

Travel to Roundstone HQ

9:00 AM – 11:45 AM

Bootcamp Pt 1

11:30 AM – 1:00 PM

Lunch & Business Break

1:00 PM – 3:00 PM

Bootcamp Pt 2

3:00 PM – 3:15 PM

Event Concludes

Complete Your Registration

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Roundstone is the original employer health insurance innovator for the middle market. We help small and midsize organizations to offer competitive health benefits at a lower cost by self-funding health insurance through our group medical captive. The Roundstone Captive enables companies to self-insure safely by pooling hundreds of employers together to share risk and save money. With easy onboarding and personalized support every step of the way, the Captive offers control, flexibility, transparency, and returns all savings back to employers where they belong. We believe in aligning with the employers’ best interests and remain committed to our mission – quality, affordable healthcare and a better life for all. 

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