The company's 1999 annual report records that "Michael J. Saylor has served as President, Chief Executive Officer and Chairman of the Board of Directors since founding MicroStrategy in November 1989". The same filing notes he holds two bachelor's degrees from the Massachusetts Institute of Technology, in aeronautics and astronautics and in science, technology and society, and that before starting the company he worked at DuPont and at Federal Group.
He no longer runs the company day to day. The annual report for the year ended 31 December 2025, filed on 19 February 2026, lists him as "Michael J. Saylor, our Executive Chairman and Chairman of the Board", separately from Phong Le as president and chief executive, and he signs that report in the chairman's capacity.
The programme he is publicly associated with is the bitcoin treasury policy the board adopted in September 2020, under which bitcoin rather than cash serves as the company's primary treasury reserve asset.