Meet the Mentors
SIIA is pleased to announce the following list of mentors who have confirmed their participation. As you will see, they represent all segments of the self-insurance marketplace (group health, captives & workers’ compensation) and each of them have been very successful in their respective careers as well as being highly involved with SIIA in various capacities. Additional mentors may be announced closer to the date, so please check back periodically to see the latest line-up.
Advantage Insurance Management (USA) LLC
Les entered the insurance business in 1977. He held senior positions with FM Global, AIG, CNA, Zurich and Willis prior to joining Advantage Insurance Management (USA) LLC. He holds a Bachelor of Mechanical Engineering (with Distinction) from Carleton University, Ottawa, Canada, and an MBA from York University, Toronto, Canada.
As Chairman of Advantage Insurance Management (USA) LLC, Les is responsible for developing Advantage’s captive insurance and related businesses globally, including its direct underwriting activity at Lloyd’s reinsured by Advantage Property & Casualty Company SPC. In his role as Managing Director of Willis Global Captive Practice, Les was responsible for the profit and growth of “The Americas” Practice with offices in Barbados, Vermont, Cayman, Bermuda and Hawaii. He is Past Chairman of the Captive Insurance Companies Association (CICA), is on the Program Committee of the World Captive Forum and Chairman of the Self Insurance Information Association (SIIA).
Charles C. Caldwell
Midlands Management Corporation
Mr. Caldwell has over fifty years of experience in the insurance industry, the majority of which have been in management positions of managing general agencies. Mr. Caldwell founded Midlands Management Corporation in 1990 and currently serves as its CEO and President. He was responsible for planning and developing Midlands from the start-up phase and continues to be the driving force in the development of new programs and in the tremendous growth Midlands has experienced. Mr. Caldwell is active in the management of a large book of primary and excess workers’ compensation business and is experienced in captive formation and reinsurance negotiation. He is recognized as an authority in self-insured workers’ compensation and insurance pools, has participated as a speaker in numerous insurance seminars, and currently serves on SIIA’s Workers’ Compensation Committee. He has received various insurance industry awards in recognition of his efforts on behalf of the property and casualty insurance industry by his involvement in trade associations, professional societies and the promotion of education-al and civic duties. Mr. Caldwell is a longstanding Coverholder at Lloyd’s of London and former member of Lloyd’s.
Director, Business Development
Windsor Strategy Partners, Inc.
Pat Campola is a Principal at Windsor Strategy Partners, Inc. as well as President of Campola Consulting and Intermediary Services. Pat has 30 years of senior management experience in the insurance industry. He is Past President of several organizations that include Alden Risk Management Services, a John Alden Insurance Co. subsidiary, Lincoln Re. Risk Management Services, a Lincoln National Insurance Co subsidiary, and John Alden International.
Jerry Castelloe founded Castelloe Partners, LLC in January 2015. As a foundation for his consulting practice, Jerry has used his expertise, relationships and experiences in the self-funding industry to assist clients with a variety of strategic endeavors. He has assisted a variety of clients, including employers, high performance networks, cost management specialists and claims administrators with strategic planning management, product development, talent identification, mergers and acquisitions, and ACA compliance.
Jerry gained valuable experience in all aspects of healthcare and self-funding during 31 years of leadership at CoreSource, Inc., a large national Third Party Administrator. During his tenure at CoreSource, Jerry provided leadership to all functional and geographical areas. Most recently, as Regional President, he led the SouthEast region and was responsible for business development, client management and administration for the clients in the region. In addition, Jerry provided strategic consulting advice to several of CoreSource’s major national clients, including the establishment and relationship management of CoreSource’s State High Risk Pool strategy.
Richard J. Fleder
President and CEO
ELMC Risk Solutions, LLC
Which he co-founded in 2013. ELMC is the latest venture in a series of successful insurance related entities he has created including Comprehensive Benefits (CBSC), in 1978, and Thesco Benefits, LLC, in 1995. Since 2013 Richard has built ELMC through the acquisition of best-in-class MGUs with funding partnership from the international investment firm J.C. Flowers & Co. Richard is a graduate of Franklin & Marshall College. He is a member of the Board of Directors of Unimerica Insurance Company of New York (Executive Committee member). Richard is a past member of the HMO Board of Directors of Oxford Health Plans and the National Advisory Councils of Aetna, CIGNA, HealthNet, and UnitedHealthcare. He is a former member of the Legislative Council of NAHU and the founder of the Empire State Healthcare Coalition.
Senior Vice President, National Health Care Practice
Risk Strategies Company
Liz brings to Risk Strategies over 25+ years of insurance and reinsurance experience. She is skilled in health, life, disability, the worksite market and a wide range of accident products, on both a group and individual basis. Well known for her talent in advising and collaborating with clients on growth strategies, product diversification and risk management techniques, Liz is equally recognized for her strong relationships within global reinsurance markets.
Liz started her career in 1982 at General Reassurance, the former life division of General Re, as an Account Manager in the Financial Reinsurance Unit and last held the position of Vice President of Treaty Operations for all individual and group life, accident and health lines of business for its successor company, Life Reassurance Corporation of America, subsequently acquired by Swiss Re.
In 1992, Liz joined Towers Perrin, where she became a Principal and held the position of Vice President responsible for business development in the Risk & Financial Services’ Life, Accident and Health Reinsurance Practice.
Liz is currently the Chair of the SIIA International Committee and a former Director of SIIA, holds an MBA from the University of Connecticut, a Bachelor of Science Degree in Pre‐Med from Boston College, and professional designations as a Chartered Financial Consultant (ChFC), a Chartered Life Underwriter (CLU), a Health Insurance Associate of America (HIA), a Certified Employee Benefit Specialist (CEBS), and a Fellow of the Life Management Institute (FLMI).
Cofounder & co-CEO
Laura Hirsch is a visionary and innovative senior executive who has more than 30 years of experience in self-funding business strategy, private labeled business process outsourcing (BPO) services, mergers & acquisitions, operational excellence and business development.
President and CEO
Health Plans, Inc.
As President, Deb leads the company's diversification growth strategy and represents the organization to parent company, Harvard Pilgrim Health Care (HPHC). Deb works with the board of directors and senior management of both companies to develop long-range goals, strategies, plans, and organizational policies.
Deb has held a number of senior executive positions over the past two decades and was a key participant during our acquisition by HPHC in 2005. Her experience and skills have directly impacted product marketing, business development, sales revenues and strategic planning, and the company’s recent risk management growth endeavors.
Deb joined Health Plans in 1993 to build our self-funded sales team as regional sales executive, serving as development architect as Health Plans transitioned operations to primarily administer self-funded health plans. Deb has since served numerous roles in the sales area including Vice President of Sales and Marketing. As Senior Vice President, Deb’s other responsibilities included Care Management and Health strategies, Reporting and Analytics, and Operations.
Earlier in her career, Deb served as an Underwriting Manager for R.E. Moulton, Director of Marketing at Mt. Vernon Associates, and was a member of the sales team at Blue Cross/Blue Shield Massachusetts.
She works closely on HPHC’s self-insured line of business strategy, serves on the Executive Leadership Committee for HPHC and is a Government Relations Committee Member for the Self Insurance Institute of America, Inc. (SIIA).
Deb holds a Bachelor of Science degree in Health Care Administration.
President and Chief Executive Officer
Since 2008, Lisa has been President and CEO for Renalogic. Lisa is responsible for overseeing and directing all strategic initiatives as they relate to People, Process and Product, while ensuring the strength of our organizational health. Lisa places a high priority on our ability to demonstrate and carry out the Renalogic mission and vision. She has been instrumental in leading the development of core values that reflect our commitment to our clients and to the industry. Lisa consistently works to create a diverse and satisfying work experience for our growing employee base. A second generational family-owned company, Lisa has been with Renalogic since its inception in 2002. She encourages and leads the disruptive entrepreneurial spirit for positive change that continues to drive the evolution of Renalogic today.
Lisa has been a longstanding member of SIIA (Self-Insurance Institute of America, Inc.) and was instrumental in promoting Renalogic, as she was one of the first cost containment consultants for SIIA Diamond members. She is also a long standing member of HCAA (Health Care Administrators Association) and an active advocate and supporter within the self-insured community to help promote industry initiatives. Lisa graduated from the University of Massachusetts Dartmouth and is a highly respected leader for change management in the health care industry.
Head of TPA & Payer Solutions and Workers’ Compensation
Prodigy Health Group
Mark Schmidt is the head of TPA & Payer Solutions, which includes Meritain Health, American Health Holding, First Health and Aetna Signature Administrators specialty businesses, and Workers’ Compensation.
Mark joined Aetna in 2007 to lead the insurer’s Strategic Resource Company (SRC), which provides limited health and related employee benefits to part-time and hourly contract workers. In 2009, he joined the Local Employers and Customers segment where he served as a local market head with oversight and responsibility for the Arkansas, North Carolina, South Carolina and Tennessee markets.
Prior to Aetna, Mark spent 13 years with CoreSource, the last 10 years as president. While serving as president at CoreSource, he also held the role of executive vice president for Trustmark, the parent company of CoreSource, leading both its operations and large group medical business. Additionally, Mark served two terms on the Board of Private HealthCare Systems (PHCS) including one term as chairman. Prior to his time at CoreSource, he spent 12 years in various financial roles with multiple insurance companies.
Harry Tipper, III
Chief Operating Officer – Insurance
CaptiveOne Advisors LLC
Harry Tipper, III currently is the Chief Insurance Operating Officer for CaptiveOne Advisors LLC (a financial services firm focused on and with the expertise required to assess, develop, and manage captive insurance and reinsurance companies successfully). Harry previously was a founder of and former President and Chief Executive Officer of Lyon’s Gate Reinsurance Company, Ltd. (“Lyon’s Gate Re”) a Class III, Bermuda reinsurance company licensed under the Act and the Segregated Accounts Act to offer reinsurance and segregated account (or rent-a-captive) cells and served on the Board of Directors of Su Vino Holdings, Inc. (an insurance and reinsurance consulting firm affiliated with ISG Group, Ltd.).