Trusted Captive Insurance Manager

Chris Gallo
Managing Director
Chris commenced his 35-year regulatory career as a Trainee in the State of Connecticut’s Financial Regulation Division. He steadily progressed through the experience and training requirements, culminating in obtaining his Certified Financial Examiner designation, and reaching the Insurance Accredited Financial Examiner position. Financial Regulation highlights include:
- A Swiss Financial Markets Supervisory Authority (FINMA) Rotation in Bern Switzerland,
- FINMA Rotation Presentation to the April 2013 NAIC’s Commissioners’ Roundtable Forum,
- Led supervisory college panel & discussion with Dutch National Bank (DNB) regulators
Being highly curious of the alternative risk markets, in 2013, Chris transferred to the newly formed Captive Division, where he reported directly to the Division Director. Captive Division highlights include:
- Devised and presented True Risk Based Captive Legislation to the Governor’s Office, and industry,
- Constructed Captive Division’s True Risk Based Examination process,
- Examiner in Charge for the Captive Division’s Report of Examinations,
- Responsible for Captive Division’s NAIC Self Evaluation Guide, Interim Annual & Accreditation Reviews
The one major lesson Chris learned from his career in insurance regulation was the critical importance of sustainable liquidity, and cash flow, in any enterprise. It is this understanding that has led Chris to pursue this second career to educate business owners on how a properly managed captive insurance company will allow such enterprise to not only survive, but to thrive, in any economic environment.
Chris received his Bachelor of Science Degree in Administrative Science from Central Connecticut State University in 1982, and his Certified Financial Examiner designation in 2012.
Chris resides in Knoxville, TN with the love of his life, his wife Serina, who together have been blessed with five children, and, to date, eight grandchildren.
Recent Industry News

The Courtroom Risk No One in Power Generation Can Afford to Ignore
In today’s energy landscape, power companies face not only the challenges of decarbonization, market volatility, and aging infrastructure but also a rapidly growing legal threat that demands board-level attention.

Captive Consolidation: Why Focused Management Matters More Than Ever
In today’s dynamic risk environment, captive insurance companies have become essential tools for businesses seeking more control over risk financing. By forming their own insurance entities, companies gain the ability to customize coverage, better manage costs, and achieve improved transparency across their risk programs. Captives are no longer just niche solutions—they’re strategic assets used by […]

CIC Services Files Second Lawsuit Against the IRS, Continuing Fight for Small and Mid-Sized Businesses
CIC Services, a Knoxville-based firm that helps small and mid-sized businesses form and manage captive insurance companies, has filed a second lawsuit against the Internal Revenue Service (IRS), challenging what it describes as a continued campaign of regulatory overreach that harms legitimate business owners. The complaint, filed in the U.S. District Court for the Eastern […]

New IRS Captive Rules Beg To Be Challenged
On January 14, just days before the end of the Biden Administration, the US Treasury continued its multi-decade-long attacks on Congressionally-authorized captive insurance arrangements by issuing a new final regulation relating to 831(b) small captive insurance companies: https://public-inspection.federalregister.gov/2025-00393.pdf. Unfortunately, the new rule very much resembles the originally proposed rule that received overwhelmingly negative feedback from […]