Kenneth Gregg is our Founder and Chief Executive Officer. Prior to founding Orion180, he served as the President of Analytical Intelligence, LLC, an IT services company. From January 2007 to March 2011, he was President and Chief Executive Officer of Citon Group, Inc., an IT solutions company, where he created programs to cover catastrophic property risk while working closely with parties at Lloyd’s of London as an authorized cover holder. From 2002 to 2005, Mr. Gregg was the Executive Sales and Marketing Director for AXA Distributors, an insurance company, where he contributed to the company’s growth for two consecutive years. Prior to his role at AXA Distributors, Mr. Gregg worked at State Street Research from 2001 to 2002, where he was responsible for building an underperforming region into a sustainable profitable territory. Mr. Gregg’s early career involved roles as Vice President and National Relationship Manager for both Allianz and CNA, leading product distribution in the United States for those organizations. Mr. Gregg holds a Bachelor of Science in Economics and a Master of Business Administration in Finance from the University of Central Florida, and served honorably in the United States Marine Corps.
Prior to his retirement in June 2024, Mr. Bollinger served as a U.S. partner at Ernst & Young LLP for over 25 years, where he was the Global and U.S. lead executive for several of the firm’s most strategic insurance accounts, including Munich Re America, Inc., Alleghany Corporation, USI Insurance Services (a KKR portfolio company), and Horizon Blue Cross Blue Shield, and oversaw multinational audit transitions working with practices in Switzerland, Germany, Spain, Japan, and the United Kingdom. Earlier in his career, Mr. Bollinger worked extensively with U.S. and Bermuda entities, and also worked for Price Waterhouse and Coopers & Lybrand. Mr. Bollinger holds a Bachelor of Science in Accounting from Syracuse University. He is a certified public accountant licensed in New York and New Jersey.
Mr. Deshpande served as the Chief Information Officer of Humana Inc. (NYSE: HUM) from July 2021 to December 2024, after previously serving as its Chief Technology and Risk Officer. Before joining Humana Inc. in July 2017, Mr. Deshpande spent 17 years at Capital One in key leadership positions, most recently as Business Chief Risk Officer for the U.S. and International Card businesses. He previously served as Business Chief Risk Officer and Head of Enterprise Services for Capital One's Financial Services Division. Mr. Deshpande also led Marketing and Analysis in Capital One's Home Loans, Auto Finance and Credit Card businesses, with responsibilities for business strategy, credit, product and marketing. Mr. Deshpande holds a Bachelor of Technology with Honors from the Indian Institute of Technology - Kharagpur, a Master of Science in Aerospace Engineering from Virginia Tech, and a Master of Business Administration with High Honors from the University of Chicago.
Since January 2019, Mr. Deutsch has served as Chairman of Pelican Ventures, an insurance-focused investment firm, and currently serves as a board member of Ariel Re since November 2020, Mosaic Insurance Holdings Limited since February 2021, and as Chairman of Tango Specialty Insurance Services since May 2021. Mr. Deutsch served on the board of IQUW Holdings Bermuda Limited (now called Starr Bermuda Holdings Limited) from February 2021 to July 2026. In addition, he continues to serve on the board of IQUW Re Bermuda Limited since February 2021 and joined the board of Starr Insurance & Reinsurance Limited in August 2026. From May 2018 to December 2020, Mr. Deutsch served as a Managing Director at GE Capital, where he led efforts to reduce risk in long-term care and structured settlement annuity portfolios. From July 2014 to December 2017, he served as Chief Strategy Officer of Hamilton Insurance Group, a global insurance and reinsurance company, and concurrently served as Chief Executive Officer of Hamilton USA from October 2015 to October 2016. Prior to Hamilton Insurance Group, Mr. Deutsch served as Chief Executive Officer of Ironshore Inc., a Bermuda-based specialty insurance company, from January 2007 to March 2009. Earlier in his career, Mr. Deutsch served as Executive Vice President and Chief Financial Officer of CNA Financial Corporation (NYSE: CNA), a leading commercial insurance company, from August 1999 to October 2004. Prior to CNA, he served as President, Chief Financial Officer and Chief Actuary of Executive Risk Inc., a specialty insurance company, from June 1987 to July 1999. Mr. Deutsch began his career as a Senior Manager at Ernst & Young and subsequently served as a Vice President at Swiss Re. Mr. Deutsch holds a Bachelor of Science in Economics from the University of Pennsylvania, with a concentration in Insurance and Actuarial Science. He is a Fellow of the Casualty Actuarial Society and a past Associate of the Society of Actuaries.
Mr. McAlee served as Senior Vice President and Chief Financial Officer of Essent Group Ltd. (NYSE: ESNT) from April 2009 until June 2022, when he transitioned to Special Advisor to the Chief Executive Officer, a role he held until his employment with Essent Group Ltd. ended in December 2022. Mr. McAlee has over 25 years of experience in finance, accounting, controls and risk management. Prior to joining Essent Group Ltd., Mr. McAlee held a series of senior management positions at Sovereign Bancorp, Inc. from August 2002 to March 2009, including serving as its chief accounting officer, general auditor and chief enterprise risk management officer. Prior to joining Sovereign Bancorp, Inc., Mr. McAlee was a partner with Arthur Andersen LLP. Mr. McAlee holds a Bachelor of Science in Accounting from St. Joseph's University and is a certified public accountant.
Since 2022, Mr. Oberting has served as a strategic advisor to Rail Modal Group, a rail intermodal terminal transportation and logistics company. Prior to Rail Modal Group, Mr. Oberting served as President and Chief Executive Officer of Sirius International Insurance Group, Ltd., a global reinsurance company, from 2019 to 2021, and previously served as its Chief Financial Officer, Director and Audit Committee Chair from 2016 to 2019. Prior to joining Sirius International Insurance Group, Ltd., Mr. Oberting served as a Senior Partner of White Mountains Capital, Inc. from 2012 to 2016, was the founder and Managing Member of Oakum Bay Capital from 2008 to 2012 and served as Executive Vice President and Chief Financial Officer of Montpelier Re Holdings, Ltd. from 2004 to 2008. Mr. Oberting also served in various capacities at White Mountains Insurance Group from 1995 to 2004 and began his career as a trader at CS First Boston (Japan) from 1993 to 1995. Mr. Oberting holds a Bachelor of Arts in Economics from Dartmouth College.