Founder | Managing Member
Wayne Jenkins is the founder and managing member of CaptiveOne Advisors LLC. He started CaptiveOne to focus on the captive insurance strategy for mid-size businesses. After 20 years of working in the insurance and financial planning industries, namely, designing asset preservation and wealth accumulation plans for business owners and medical practitioners, he moved his focus solely to provide business owners and professionals a solution of customized insurance that secondarily provides economic, tax and estate planning benefits, namely, a captive insurance company. CaptiveOne Advisors offers a turnkey solution to business owners—making it easy to add captives to the mix of insurance and financial business strategies.
In just three years time, CaptiveOne Advisors has had a significant impact on the U.S. domestic captive marketplace. Wayne’s ability to build a team of in-house captive experts and his knowledge of the needs of business owners has catapulted CaptiveOne into the forefront of captive providers.
Wayne Jenkins is known for his accomplishments in the insurance industry in general. He has been recognized for sales and financial planning by industry leaders many times throughout the years. He is licensed to practice in 36 states. Earlier in his career, his degree in computer sciences led him to develop numerous innovative insurance-related software products and to own several successful companies related to insurance sales tracking and the insurance e-consumer.
Jason Byers is the President of CaptiveOne. He is responsible for managing and overseeing day to day operations at CaptiveOne. He comes to CaptiveOne with a Bachelor of Science in Engineering Science from the University of Florida, and a Masters in Bioengineering from the University of Pennsylvania, and holds a Certificate in Engineering Management from Drexel University.
Jason comes to the CaptiveOne team with 6 years of experience in the insurance industry as the Director of Product Development for the iCan Benefit Group. Prior to iCan, Jason was engaged in the elite Operations and Leadership Development Program (OLDP) at Lockheed Martin. During his tenure he served as a Process Engineer, Manufacturing Engineer, Engineering Planner, Test Engineer, and completed a Lean and Six Sigma Green Belt. His strong analytical and engineering background adds a unique skill set to the operations area.
Diane Sugimoto, CPA
Chief Financial Officer
Diane Sugimoto, CPA is the Chief Financial Officer for CaptiveOne. She is a Florida licensed Certified Public Accountant with over 35 years of experience in guiding companies’ capital efficient, profitable growth and maximizing their value. Diane adds a macro financial and operational perspective, resulting in an organization’s ability to assess top level strategy and achieve lean growth. At a micro level, her deep understanding of entity design, measurements and reporting, and business and financial modeling, combined with her unique proficiency in integrating systems and business culture is an essential asset in driving a project’s overall success.
Diane has played a primary role in comprehensive strategic planning, budgeting, data analysis, and risk management. She has effectively guided all major financial transactions, including acquisitions, partnerships, and investments. Diane has leveraged her advanced technical knowledge and broad business experience to create the strategic architecture, infrastructure, and financial design to build solid, compliant, profitable rapid-growth companies. Having been involved in a broad range of highly regulated industries, including insurance and healthcare, Diane has successfully overseen the creation and implementation of innovative operational concepts, programs and techniques that turn corporate strategies and consumer trends into market share.
Diane earned her Bachelors of Science degrees in both Marketing and Finance and a Master’s in Accounting with a specialty in Internal Controls, from Florida International University (FIU). She currently serves on Boards of Directors of the FIU School of Integrated Science and Humanities, and the Florida International University Research Foundation, Inc.
Chief Operating Officer
Director of Client Services | Co-founder
Bryan Jenkins is a co-founder and director at CaptiveOne. He specializes in creating and implementing business processes and strategies.
Bryan is an active member of the World Organization of Web Masters as well as AIGA – the Professional Organization for Design.
Amanda S. Luby
General Counsel and Executive Vice President
Amanda S. Luby is General Counsel and Executive Vice President of CaptiveOne Holdings, LLC and its affiliates (“CaptiveOne”). Prior to joining CaptiveOne in March 2017, Amanda was a partner at one of Florida’s largest and oldest firms, Shutts & Bowen, LLP. With an extensive track record in claims assessment and processing, Amanda has been a national speaker on insurance coverage issues in the construction and agricultural industries. She also served as national general or local counsel for several international or large, privately held corporations while working at Shutts & Bowen, and brings to CaptiveOne a diverse breadth of experience that bridges corporate, transactional, litigation, and product development proficiencies. Amanda earned her Juris Doctor from the University of Kentucky with several honors and her Bachelor of Sciences Degree (Business) from the Oklahoma State University Department of Agricultural and Natural Resources, also with honors.
Harry Tipper, III
COO - Insurance
Harry Tipper, III is Chief Operating Officer of Insurance at CaptiveOne. He is the 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 segregated account (or rent-a-captive) cells. Between 2000 and the formation of Lyon’s Gate Re in 2004, Harry oversaw a boutique consulting practice, affiliated with REcoverRE, LLC in Connecticut, where he assisted clients to improve business development, underwriting, and administrative activities and served as an expert witness in reinsurance litigation and arbitration. He began his career in 1973 in the Underwriting Department of the National Council on Compensation Insurance (“NCCI”). In 1975, he joined the New York office of General Reinsurance Corporation as a Casualty Facultative underwriter in 1975 and quickly advanced to a senior underwriting and officer position in its Home Office Facultative Division (in Connecticut). In 1988, Harry, serving as a Vice President, participated in the formation of the General Re subsidiary Genesis Underwriting Management Company and oversaw the formation and/or acquisition of its subsidiaries and affiliated companies. The Zurich-American Insurance Group recruited him to Illinois in 1993 to originate a business unit to secure Zurich-American’s place in the self-insurance and "ART" business, where he served as Senior Vice-President. In 1997, the Duncanson & Holt Group in New Jersey asked him to join its senior management team tasked with turning around its North American Reinsurance Division and serving as its Underwriting Director for facultative and treaty, Workers’ Compensation, Occupational Accident, and Casualty reinsurance business, a position that he held until Duncanson & Holt’s sale in early 2000.
Harry holds a Bachelor of Arts from Cornell University’s College of Arts and Sciences (awarded in 1973) and a Master of Business Administration in International Finance from New York University’s Stern School of Business (awarded in 1980). He has written and lectured extensively, conducting workshops and briefings for numerous trade associations including International Association of Accident Boards & Commissions, the Risk & Insurance Management Society, and the Self-Insurance Institute of America. He, also, has been a lecturer with university continuing education and executive development programs and for local, state, and federal governmental agencies in both the United States and Canada. He is certified arbitrator with ARIAS-US, was Chair of the Self-Insurance Educational Foundation, and a former Director of the Bermuda Captive Owners Association.
Paul Chabarek, ACAS, MAAA
Vice President and Actuary
Paul Chabarek, ACAS, MAAA serves CaptiveOne as Vice President and Actuary. His actuarial career began with over a decade in the home office of The Travelers in Hartford, CT. Several other roles followed, including four Chief Actuary positions and consulting. He is an Associate of the Casualty Actuarial Society, with credit for one of the three remaining exams required for Fellowship in the Casualty Actuarial Society, and a Member of the American Academy of Actuaries. He is proud to have been selected to join the team of captive experts being built by Founder Wayne Jenkins.
Paul has a wealth of experience in many different property/casualty lines of business, both commercial and personal. His wide-ranging background is an asset to CaptiveOne clients as it includes loss projections, reserving, pricing, profitability analysis, financial reporting, forecasting, product development, and other related disciplines encompassing most aspects of insurance operations.
Paul earned his bachelor’s in mathematics, Magna Cum Laude, from the State University of New York in three years.
Louis J. Estrema
Director of Risk Assessment
Louis J. Estrema is Director of Risk Assessment at CaptiveOne. Lou coordinates clients’ need for risk analyses with the underwriting and actuarial teams. Lou is a highly qualified risk management specialist with over 35 years in the insurance, reinsurance and risk management industries. He has spent his career working with clients in the identification, quantification and mitigation of risk including risk transfer to both traditional and non-traditional markets. Before joining CaptiveOne, Lou was director and client relationship senior account executive with ABS Consulting, EQECAT, Inc. in Hackensack, N.J. providing clients practical, rational and holistic risk management systems and solutions. His clients included, but were not limited to, Bermuda reinsurers, primary insurance companies, reinsurance brokers and financial institutions. Before that, Lou worked at Gallagher RE, Inc. (formerly John P. Woods Co., Inc.), a subsidiary of Arthur J. Gallagher & Co., one of the world's largest insurance brokerage and risk management services firms that provide a full range of retail and wholesale property/casualty (P/C) brokerage and alternative risk transfer services globally. Lou served as senior vice president, reinsurance broker. Earlier in his career, Lou served as vice president at Applied Insurance Research, Inc. in Boston and at Guy Carpenter & Co., Inc. in New York. Lou was on the formation team for Mid-Ocean, the first Bermuda-based catastrophe reinsurers. He is a member of the International Society of Catastrophe Managers.
CJ Ehrenberg is the Creative Director at CaptiveOne. He is responsible for graphic design, web services, video production, brand continuity and all other creative communications. He attended Florida Atlantic University and Palm Beach State College and has a degree with focus in Graphic Design.
In 2010 CJ was awarded first place in the 25th Annual Art Exhibition at The Art Gallery at Eissey in Palm Beach Gardens, Florida, for a painting titled “Color Designed” which showcased a strong understanding of layout and composition, relationships of colors, and figure-ground relationships.
In 2012 CJ was given the privilege of becoming a part of The Florida Atlantic Graphic Design Program after only one portfolio submission showcasing his previous works in the fields of design fundamentals, typography, layout and composition, color design, figure drawing, and craftsmanship.
In 2014 CJ was invited to join the exclusive graphic artists community, Dribbble. Upon joining, his design “Icebreaker” was recognized as the #1 debuted piece for over a week.
Michael S. Bernstein
Michael S. Bernstein heads up Underwriting at CaptiveOne. Mike ensures that all accounts are rated and issued according to the CaptiveOne standards, and that the Client’s insurance needs are properly addressed. He brings over 30 years’ experience in the Insurance Industry to CaptiveOne, primarily developing and managing Underwriting Products and Programs. Mike’s specialized expertise is in the areas of Professional Liability and Medical Malpractice coverages. His career has overseen all facets of underwriting; including profitability, production, management, budgeting P&L, and reinsurance placement. Mike has lead organizations successfully through the startup phase and managed turnarounds of underperforming divisions and products
Most recently Mike was President of the Professional Programs lines at Admiral Insurance Company, where he started up the Programs Group. This included building out the back office, developing product forms and rates, and marketing the products to Agents. The majority of Mike’s career was spent at various profit centers of AIG, in increasingly senior roles. This includes the management of the Healthcare Programs Division of the Lexington Insurance Company, where Mike grew the book of business from $28 mm to almost $200 mm in a few short years. Mike is a member of a number of insurance organizations, including the Professional Liability Underwriting Society (PLUS), Target Markets and the John Street Insurance Association.
Executive Vice President
Jim brings 30 years of experience as an entrepreneur to his role as Executive Vice President of CaptiveOne. Jim directs CaptiveOne’s sales and marketing group and the company’s new product development efforts. He originally joined CaptiveOne as an independent sales representative 2013. Prior to joining CaptiveOne, he served as CEO of a start-up technology company (GeoToll, Inc.), and was an owner and CEO of one of the largest orthopedic bracing/DME businesses in the South East (Florida Bracing Centers, Inc.). During his tenure as CEO of FBC, he was responsible for driving a four-fold increase in the company’s revenue over six years while maintaining industry-leading profitability. Earlier, Jim purchased and profitably grew a hotel construction business from $3MM in annual sales to over $20MM in two years and exited through a sale to partners. He spent the first 15 years of his career in consulting engineering where he successfully founded three consulting businesses and exited each through a sale to larger entities or an employee buyout. He graduated from the Colorado School of Mines with a Bachelor of Science degree in Geophysical Engineering.
Director of Technology
V.P. Business Development
April De Los Reyes
Miranda Van Kol
Venue Manager Coordinator