
SIIA will connect many of its younger members with some of the top self-insurance industry leaders for small-group career mentoring sessions delivered through a dynamic virtual platform. We'll close out the event with a dedicated virtual happy hour for attendees to network with each other.
This will be a truly unique opportunity for our industry's rising stars to accelerate their career growth by speaking directly with those who have achieved significant success within a variety of companies and have supported SIIA's mission in various capacities.
With the virtual format, participation is easy and affordable.
This event is part of an ongoing membership engagement campaign developed by the SIIA Future Leaders Committee. The self-insurance industry has started to witness a significant generational change, with an increasing number of its long-time leaders transitioning into retirement. If you are a younger (under 40) self-insurance/captive insurance industry professional, this is a must-attend for you.
schedule*
| 1:00 p.m. - 1:30 p.m. | Welcome Remarks & Directions |
| 1:30 p.m. - 4:30 p.m. | Small Group Mentoring Sessions Small groups will rotate among designated mentors every 20-30 minutes for the duration of this time block. |
| 4:30 p.m. - 5:00 p.m. | Virtual Networking We will excuse the mentors, and the participants can take this time to network virtually with each other. |
*Eastern Standard Time
registration fees
The Mentor Connection Live Stream is designed for our Future Leaders that are under the age of 40 years old. Proof of age will be required during the registration process.
| Registration Type | Early-Bird By 11/16/2026 |
Regular After 11/16/26 |
|---|---|---|
| SIIA Member | $100 | $125 |
| SIIA Additional Member | $75 | $100 |
| Non-Member | $195 | $250 |
Click a mentor's name to learn more about their industry experience and background.
Dave Cardelle, R.Ph.
Chief Strategy Officer
Advanced Medical Strategies |
John Cooper
Senior Vice President - Affinity Markets
SevaRx, LLC |
Jason Davis
Strategic Executive Advisor, Sales and Revenue
The Phia Group, LLC |
Erin Duffy
Senior Director of Business Development
Imagine360 |
Jeremy Freestone
SVP, Stop Loss Business Strategy
Symetra Life Insurance Company |
Matt Hayward
Office President
Ryan Specialty Benefits |
Jordan Smith
Practice Leader
Lumelight |
Rachel Strauss
Founder/CEO
PBM Princess, LLC |