overview

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
Cancellation Policy:
1. All cancellations must be received in writing to registration@siia.org.
2. Written cancellations received before November 16, 2026, will be eligible for a 50% refund, less an administrative fee of 3%.
3. Written cancellations received between November 17 - November 24, 2026, will receive a 25% refund, less an administrative fee of 3%. 
4. Cancellations made after November 24, 2026, and all no-shows are NOT eligible for a refund. 
5. Substitutions are permitted for the 2026 Future Leaders Mentor Connection only and cannot be transferred to another event in 2026. 

Meet the Mentors

Click a mentor's name to learn more about their industry experience and background.

Dave Cardelle
Dave Cardelle, R.Ph.
Chief Strategy Officer
Advanced Medical Strategies
John Cooper
John Cooper
Senior Vice President - Affinity Markets
SevaRx, LLC
Jason Davis
Jason Davis
Strategic Executive Advisor, Sales and Revenue
The Phia Group, LLC
Erin Duffy
Erin Duffy
Senior Director of Business Development
Imagine360
Jeremy Freestone
Jeremy Freestone
SVP, Stop Loss Business Strategy
Symetra Life Insurance Company
Matt Hayward
Matt Hayward
Office President
Ryan Specialty Benefits
Jordan Smith
Jordan Smith
Practice Leader
Lumelight
Rachel Strauss
Rachel Strauss
Founder/CEO
PBM Princess, LLC
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Dave Cardelle
Dave Cardelle, R.Ph.
Chief Strategy Officer
Advanced Medical Strategies
David Cardelle, R.Ph., is AMS' Chief Strategy Officer. David joined AMS in June 2021 and is a Registered Pharmacist with an extensive 30+ year experience in the healthcare industry. Leveraging years of expertise and domain knowledge in the payment integrity (PI) industry, David worked with various health plans and companies to evaluate, advise and improve PI outcomes.

David's keen business acumen for strategic planning, depth of industry knowledge, and impressive track record in developing innovative payment integrity solutions will continue to transform the payment integrity industry and affordability.

He has worked in various key roles as a Provider, working in retail and hospital pharmacies, as a Payer, working for a large BCBS plan as well as a regional HMO in Cambridge, MA, and as an outsourced Payment Integrity Partner, working with dozens of health plans across the U.S.

Most of David's career has been dedicated toward developing and managing new, innovative payment integrity solutions for the Payer industry. He pioneered the first outsource audit service for specialty injectable overpayments as well as developed and managed Hospital Bill Review, DRG Validation, Home Infusion, Renal Dialysis, DME and Implant Audit and Recovery programs. Most recently, David helped to develop a unique transaction-based delivery model to help automate a variety of pre-submission payment accuracy solutions.

David has a BS in Pharmacy from the Massachusetts College of Pharmacy, Boston, MA.
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John Cooper
John Cooper
Senior Vice President - Affinity Markets
SevaRx, LLC
Player Coach at S&S Healthcare Strategies. Chief Growth Officer and Director of Sales & Innovation experience extends over 15 years with an impressive average annual year over year revenue growth. Key and unique experience with all areas of employee benefits from Administration and PBM to 340B and cross functional products. Career totality in this space of 20 years. Solid relationship based in the Broker, TPA and Program Manager areas of the distribution space. Adept at streamlining sales effectiveness and becoming a more efficient sales unit. Understand how to prioritize cost containment, CFO needs, HR needs and member experience. Experience with HMO, MCO, PPO health and prescription plans, PBM services and 340B for Covered Entities.

In the fast-evolving healthcare sector, my role involves pioneering product development and setting market trends. Leveraging expertise in financial risk management and customer retention, we've supported hospitals, employers, and carriers in constructing robust health insurance plans, driving change in how healthcare is delivered and purchased within our communities.
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Jason Davis
Jason Davis
Chief Revenue Officer
The Phia Group, LLC
Jason C. Davis is the Strategic Executive Advisor, Sales and Revenue at The Phia Group, LLC. Mr. Davis joined The Phia Group in 2014; prior to this, he was Vice President U.S. Markets for another cost containment company, where for nearly 10 years, he contributed at various levels of claim settlement, dispute resolution, R&D, product development, sales, and leadership.

Mr. Davis also founded JCDC in 2014, which is a cost containment company that catered to international payers with exposure in the U.S. In order to expand its reach into international markets, The Phia Group acquired JCDC in 2020. As such, Mr. Davis' network of industry partners, contacts, and clients is spread all over the world.

Jason or "Jay" (as he is so often called) is a self-professed and proud "nerd." He is a consistent contributor to industry periodicals and a regular speaker at conferences that address medical cost containment issues for multiple insurance industries. Jason loves to work hard, play hard, travel, and spend time with his wife, Kim, and their four children – Aleithea, Kairus, Xeidan, and Mohzen.
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Erin Duffy
Erin Duffy
Director of Business Development
Imagine360
With 15+ years in the benefits space, Erin is dedicated to honesty and relationship building. She started her career at Arthur J. Gallagher focusing on public sector employers and coaching clients to develop a thoughtful and intentional approach to health insurance. In 2016, Erin channeled her entrepreneurial spirit and joined a start-up, Gravie, where she worked with small and mid-sized companies to make benefits more approachable and affordable. Following her path to growth and helping organizations navigate healthcare, Erin joined Imagine360 in 2018. Here she works with employers, brokers, consultants, and third-party administrators (TPAs) to access a transparent cost-containment solution – reference-based pricing. She graduated with her MBA from DePaul University and undergraduate degree from Bradley University. Erin loves to travel, golf, exercise, and spend time with friends and family, and is currently pursuing her Pilates teacher certification.
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Jeremy Freestone
Jeremy Freestone
SVP, Stop Loss Business Strategy
Symetra Life Insurance Company
I am a senior insurance executive with over 20 years of experience leading complex, high-stakes businesses across actuarial, underwriting, pricing, claims, sales, and strategy.

Currently, I serve as Senior Vice President leading Symetra's Stop Loss Business, where I lead a $1.5B, sustainably profitable specialty health risk portfolio with full P&L responsibility. My role spans underwriting and pricing discipline, claims operations, reinsurance strategy, product development, distribution, and technology modernization.

Over the past several years, I have focused on building durable, profitable growth in an increasingly volatile medical cost environment – strengthening pricing governance, improving portfolio segmentation, and leading multi-year transformations across underwriting, claims, and data/analytics. I am deeply involved in deploying AI-enabled underwriting and claims automation to improve risk selection, cycle time, and customer outcomes.

My leadership style emphasizes disciplined decision-making, long-horizon thinking, and building high-trust, high-performance teams in regulated, high-consequence environments.

Earlier in my career, I came up through actuarial leadership, which continues to shape my approach to strategy, risk management, and capital efficiency.

I am a Fellow of the Society of Actuaries and a member of the American Academy of Actuaries.

Outside of work, I am passionate about technical scuba diving, aviation, and classical music – pursuits that reinforce preparation, discipline, and mastery.
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Matt Hayward
Matt Hayward
Office President
Ryan Specialty Benefits
I am the Office President at Ryan Specialty, a leading provider of self-funded employee benefit plans and stop-loss insurance. With national experience across all aspects of self-funding and over 20 years of direct sales experience in the health benefits sector, I have a deep understanding of the challenges and opportunities facing employers and producer partners in an ever-changing market.

My mission is to deliver best-in-class stop-loss coverage, cost containment solutions and comprehensive strategy, to protect financial risk and enhance employee well-being.

I work collaboratively with our underwriters, clinicians, and service teams, as well as with our broker, TPA, and vendor partners, to create innovative and customized strategies that meet the diverse needs of our clients.

I also leverage our investments in AI technology and preferred carrier arrangements to optimize our performance and outcomes. I am passionate about building long-term relationships and mutual trust with our partners and clients, and I enjoy sharing my expertise and insights through publications and presentations.
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Jordan Smith
Jordan Smith
Practice Leader
Lumelight
Jordan O. Smith is a benefits compliance consultant, entrepreneurial co-founder, and Practice Leader at Lumelight. With more than 15 years of leadership experience spanning the nonprofit, higher education, startup, financial, and legal sectors, Jordan has held senior roles including Chief Operating Officer, Chief Compliance Officer, and Principal Consultant.

Jordan is recognized not only for his subject-matter expertise, but also for his ability to build organizations, lead teams, and scale operations in complex regulatory environments. He has advised executives, boards, and industry leaders on compliance strategy, risk mitigation, and operational excellence. Beyond Lumelight, Jordan is a co-founder and partner in multiple ventures and Chairs the Board of Directors for Gateway House, a nonprofit supporting individuals living with severe mental illness.

A graduate of Wofford College, Jordan lives in Greenville, SC. He remains active in his community through Westminster Presbyterian Church, where he volunteers as a Youth Advisor and sings baritone in the Sanctuary Choir. Outside of work, he enjoys traveling, reading, practicing yoga, and exploring the Swamp Rabbit Trail.
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Rachel Strauss
Rachel Strauss
Founder/CEO
PBM Princess, LLC
Rachel Strauss is the Founder and CEO of PBM Princess, LLC, a healthcare consulting firm dedicated to improving access, education, and advocacy in the most overlooked corners of care – especially those impacting women. With over two decades of experience in the health insurance and pharmacy benefit space, Rachel has helped employers, startups, and patient-centered innovators bring their solutions to market and drive change across the healthcare ecosystem.

Rachel began her career as employee #11 at a regional PBM, eventually helping it scale into a national powerhouse. Along the way, she became a nationally awarded sales executive and later pivoted to executive leadership, overseeing strategic development and partnerships.

Today, through PBM Princess, she works with companies on go-to-market strategy, cost-containment solutions, and benefit plan redesign – bringing clarity to complex systems and ensuring patients aren't left behind. Her clients include third-party administrators, digital health platforms, and mission-driven PBMs, but her advocacy runs deeper than business. As a woman navigating perimenopause herself, Rachel is passionate about shifting the cultural narrative around midlife health. She believes menopause should be met with support, not stigma – and she's committed to helping employers, healthcare leaders, and communities respond with care that actually meets women's needs.

In addition to her consulting work, Rachel hosts the Insfluencers podcast, sits on multiple nonprofit boards, and is a sought-after speaker on pharmacy benefits, women's leadership, and healthcare innovation. She's known for her signature style of simplifying what feels impossible – and connecting people, platforms, and ideas to make healthcare more human.

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