PGR: Leadership change · Company disclosure

Item 5.02 Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers. (b) On June 17, 2026, The Progressive Corporation (the “Company”) announced that Patrick K. Callahan intends to retire from his role as Personal Lines President in January 2027. After that time, Mr. Callahan intends to continue contributing to the Company’s success by advising the executive team on topics of strategic importance. The terms of that arrangement are under discussion. In connection with the orderly transition of the Personal Lines President role, on July 4, 2026, Lori Niederst, the Company’s CRM President, will be promoted to a newly created role of Chief Personal Lines Officer, overseeing both the Personal Lines business and the CRM operations. In addition, on July 4, 2026, Heather Day, the Company’s General Manager, Customer Experience Strategy, will become the Company’s next CRM President. The Company’s press release announcing Mr. Callahan’s retirement and other management changes is attached hereto as Exhibit 99.2. (c) This disclosure amends and supplements the Company’s Current Report on Form 8-K, filed on May 12, 2026. On June 11, 2026, the Compensation and Talent Committee (the “Committee”) of the Company’s Board of Directors approved, effective July 4, 2026, Andrew J. Quigg’s annual compensation package as the Company’s Vice President and Chief Financial Officer (“CFO”), which includes an annual salary of $700,000 and a Gainshare target percentage of 150% of salary. Additionally, the Committee approved granting equity awards to Mr. Quigg on July 20, 2026, comprised of a $100,000 time-based restricted stock unit (“RSU”) award and a $1,200,000 performance-based (performance versus market) RSU awa