Management Team
Jessica Buss has served as the Chief Executive Officer of Open Lending since March 2025. Ms. Buss has served on our board of directors since August 2020 and has served as chairman of our board of directors since July 2023. Ms. Buss previously served as the chief executive officer of Argo Group International Holdings, Ltd, a subsidiary of Brookfield Wealth Solutions Ltd. (NYSE, TSX: BNT) from November 2023 until March 2025. She was previously the President, U.S. Insurance, of Argo Group prior to its acquisition by Brookfield from August 2022 until November 2023. Previously, Ms. Buss served as the president and chief executive officer of GuideOne Insurance Company from 2017 until her resignation in April 2022, and prior to that, she was senior vice president—Commercial and Specialty Lines at State Auto Insurance Companies. Ms. Buss held several other positions during her tenure at State Auto, including chief operating officer and chief financial officer of the company’s specialty subsidiary, and senior vice president of Specialty. Prior to joining State Auto, Ms. Buss was a member of a three-person team that raised the capital for the formation and start-up operations of Rockhill Holdings, a niche property and casualty business that was purchased by State Auto in 2009. She was also the chief financial officer for Citizens Property Insurance Corporation. In 2016, Ms. Buss was named one of Insurance Business’ Elite Women of the Year. Ms. Buss has a bachelor’s degree in accounting from the University of Wisconsin and a Master of Business Administration from the University of Florida.
Massimo Monaco has served as the Chief Financial Officer of Open Lending since August 2025. Prior to joining Open Lending, Mr. Monaco was Chief Financial Officer of Arc Home LLC, a residential mortgage lender from December 2018 to July 2025. From December 2016 to December 2018, he served as the Chief Financial Officer at American Financial Resources, a national residential mortgage lender. Before that, he held various senior finance roles at PHH Corp., a public company specializing in residential mortgage and fleet leasing. Mr. Monaco received a Bachelor of Arts degree and a Master of Business Administration degree from La Salle University.
Michelle Glasl has served as the Chief Operating Officer since March 2025. Prior to her appointment as Chief Operating Officer, Ms. Glasl served as the Head of Operations of Argo Group International Holdings, Ltd. a subsidiary of Brookfield Wealth Solutions Ltd. (NYSE, TSX: BNT), from November 2023 to March 2025. From September 2022 to November 2023, Ms. Glasl served as SVP of Strategy and Business Development at Argo Group. Prior to that, she served as Chief Information Officer at GuideOne Insurance from June 2017 to June 2022. She previously served as Vice President of Technology at State Auto from February 2009 to June 2017. Ms. Glasl has a Bachelor of Science degree from the University of Wisconsin - Milwaukee.
Ben Massey has served as the General Counsel and Corporate Secretary of Open Lending since November 2025. He previously served as Assistant General Counsel of Open Lending from January 2024 until November 2025 and as Corporate Counsel – Securities and Governance of Open Lending from October 2022 until December 2023. Prior to joining Open Lending, Mr. Massey was an attorney with Simpson Thacher & Bartlett LLP from June 2019 until September 2022. Mr. Massey holds a Bachelor of Arts degree in Politics from Princeton University and a J.D. from the University of Virginia School of Law.