Leif O’Leary

Leif O'Leary is a seasoned software industry executive with over 25 years of leadership experience, currently serving as Chief Executive Officer at Alegeus since December 2020. O'Leary has held key positions in various companies, including Executive Partner at Waud Capital Partners, Member of the Board of Directors at ActiveViam, and Chief Executive Officer at Intralinks. O'Leary has a demonstrated track record in sales, operational excellence, and go-to-market strategy across multiple software sectors. Previous roles include Executive Vice President at Synchronoss Technologies, where accountability for a $300M business was managed, and several senior vice president roles at Parametric Technology Corporation, culminating in oversight of a $270M sales budget. O'Leary began a successful career in sales at ADP, consistently achieving top rankings and recognition. O'Leary holds a Bachelor of Arts degree in Political Science with a minor in Marketing from Boston College and attended Kimball Union Academy.