Team

Tom is a 27-year veteran in the commercial specialty P&C program arena, with experience working at both carriers and program administrators. Tom is currently President at Totalis Program Underwriters, a brand that includes 20 distinct programs representing $950 million in annual gross written premiums. Prior to Totalis, Tom owned and operated EverGuard Insurance Services, Inc., a program administrator specializing in the restaurant, bar and tavern industry. Prior to that, Tom was the CEO and owner of another program administrator, Gillingham & Associates, Inc., the leading underwriter of outdoor recreation and hospitality businesses in the US. Tom sold Gillingham & Associates to Philadelphia Insurance Company in 2008 and remained on as president until 2010 to successfully oversee a smooth transition of the business. Tom graduated from Baylor University in 1997, where he studied marketing and risk management. He is Advisory Board President of the Target Markets Program Administrators Association and has served in an advisory board capacity for philanthropic organizations and for the Colorado chapter of Young Presidents’ Organization (YPO).

John began his insurance career in 1988 and progressed to hold leadership roles for several national insurance companies over the next two decades, including Great American, GE Capital, Guaranty National, Kemper, Arch and Asurion. In 2006, John joined Gillingham & Associates as a partner and COO. The company was sold in 2009, and that same year John co-founded iMGA, where he continues to serve as Chairman of the Board. John acquired EverGuard Insurance Services in 2012, and subsequently acquired other MGU businesses to expand EverGuard’s market position. John continues working as a President of EverGuard and as Managing Director of Totalis Program Underwriters, with oversight responsibility for 20 MGU programs and more than $950 million of annual premium, in addition to merger and acquisition activities.

Dan joined Totalis Program Underwriters as Senior Vice President in January 2021. Prior to that he was the CUO of Clear Blue Insurance Group where he underwrote numerous programs and MGA opportunities. His insurance expertise spans across multi-line commercial P&C business with core competencies that touch upon: Account Underwriting, Actuarial, Auditing, Rate/Rule/Form Development, Statutory Compliance, Pricing, (ERM) Enterprise Risk & CAT Management, Loss Control, Claims, and P&L Analytics. He has also served a wide variety of commercial industries including outdoor recreation, marine, transportation, moving & storage, manufacturing, municipalities, landscapers, staffing, mining, aviation & satellite, small commercial and more. In his role at Totalis, Dan is responsible for the Outdoor Insurance Group (OIG) while also assisting in the oversight of a “Best Practices” management approach across all existing programs and insurer relations with the goal of long-term sustainability. Dan holds a Certified Insurance Counselor (CIC) designation, and both a Master of Business Administration & Bachelor of Science in Business Marketing from Miami University.

Nate has been a Totalis leader since the beginning. He and his partners sold their international insurance, cross-border Mexico program business to Totalis, and he continues to successfully run that program business. As the Digital leader for Totalis, Nate drives digital strategy with an emphasis on enhancing technology advancements and focusing on standardization, scale and growth. He brings extensive digital experience in managing IT teams and change control processes, optimizing key carrier relationships, and new program creation. Prior to working with Totalis, Nate was the Head of Digital Transformation with NFP Property and Casualty Services, Inc, where he helped them guide and drive the overall digital strategy for all of P&C. Nate was born in Canada, has lived in Mexico and is now based in the US. He is fluent in Spanish. Nate earned his Bachelor of Science in marketing (Spanish and international business minors) while playing basketball at the University of Idaho. He also earned his MBA from Northern Arizona University.

Stephen brings nearly 20 years of experience in insurance, reinsurance, underwriting and operations across the retail and MGA segments. He currently serves as Managing Director of Insurance Specialty Group (ISG), which became part of Totalis Program Underwriters through acquisition in 2020. Since joining ISG in 2010, Stephen has overseen all underwriting and operational activities. 

Prior to ISG, he spent nearly five years at Marsh in Atlanta, working in casualty brokerage within the Global Risk Management division. He holds dual bachelor’s degrees in risk management and insurance and entrepreneurship from Florida State University and remains active in several Florida State associations. 

Stephen is licensed as a Property and Casualty insurance producer in most states and has proudly served on the board of the Voila Foundation since 2016. 

Melody joined Totalis Program Underwriters in 2025 as Vice President to help manage and facilitate all program objectives and initiatives. Prior to Totalis, Melody spent more than two years as Director of Underwriting and Insurance Partnerships at Procore, creating and managing all aspects of underwriting and building strategic partnerships across the entire insurance ecosystem. Melody began her career at DBH Resources/Aon as Director of Operations in construction risk management. She then spent 10 years as part of Cove Programs Insurance Services, serving as Vice President of US Operations, US Compliance Officer, Underwriter and Claims Advocate for the renowned construction MGA. Melody has held operational management, loss mitigation, regulatory compliance and underwriting roles in the worldwide insurance industry since 2006. Melody attended and received both her bachelor’s and Juris Doctor from the University of Southern California. 

Jonathan has been providing actuarial and analytical services to the P&C insurance sector for 20 years. He is Chief Actuary and leads the P&C Actuarial and Analytics team at Totalis Program Underwriters. Jonathan has worked for various national insurance companies. Prior to joining Totalis, he was the Chief Pricing Actuary for Arch Insurance Company. He has extensive risk quantification experience in personal, commercial and specialty lines of business, including providing solutions for program businesses, risk management clients, complex structures and the development and implementation of predictive models. Jonathan is a graduate of Gustavus Adolphus College with a bachelor’s in applied mathematics and statistics and is a Fellow of the Casualty Actuarial Society and a member of the American Academy of Actuaries.

Regina Riedel is a seasoned insurance executive with more than 25 years of experience in underwriting and operational leadership within the managing general agency space. As the current Vice President of operations for Totalis Program Underwriters, she leads key strategic initiatives focused on building scalable operating models, improving underwriting and employee experiences, while supporting the integration and growth of Totalis businesses. 

Prior to joining Totalis, Regina served as Vice President of operations for Insurance Specialty Group, where she played an instrumental role in designing and executing the firm’s long-term operational strategy. 

Regina holds a Bachelor of Business Administration in risk management and insurance and a Master of Business Administration. She also holds the Chartered Property Casualty Underwriter designation.