Bob Brennan, executive coach, is an esteemed director and former CEO with a strong background in technology and startups.

Bob Brennan

  • Former Chairman/CEO


Bob Brennan


Bob Brennan is an esteemed director and four-time CEO with a strong background in software and technology startups.  He brings his clients extensive experience navigating disruptions to legacy business models, team formation, fundraising, and M&A. Brennan has a proven track record of building leaders, as at least half a dozen of his direct reports have gone on to become CEOs. His areas of expertise include SaaS, cloud computing, and leading through transformation. 

Career History

Bob Brennan currently serves as Chair for Fairwinds and BitSight. He also serves as Chair of the Comp & Talent Committee for ThoughtWorks and a director for Transifex. Additionally, he serves as an advisor and mentor at EForAll and BECMA, both associated with helping underrepresented groups achieve entrepreneurial aspirations and attract capital for their businesses. Previously, Brennan was an Executive Director for CA Technologies after being Chairman and CEO of Veracode, which was acquired by CA in March 2017. He also served as a board member for Click (acquired by SFDC), CloudHealth (acquired by VMWare), and Copanion, Inc. (acquired by ADP).

Prior to joining Veracode, Brennan was CEO of Iron Mountain, an S&P 500 company focused on information protection with 20,000 employees in 38 countries. Iron Mountain was an early innovator in data storage, information protection, and chain of custody security. During his time as CEO, Iron Mountain’s revenue grew from $1.8B to $3.2B, including a SaaS business that grew from approximately $30M to $225M

Previously, Brennan was Chairman and CEO of Connected Corporation, a pioneer in SaaS storage which was acquired by Iron Mountain. Connected was an early adopter of the recurring revenue business model and what is known as SaaS today. In this role, Brennan built a high-performing team that went on to run big components of Iron Mountain. About a half dozen of his directs have gone on to become CEOs. Veracode- successor- a woman of color who sold the company for 2.5B – John Clancy – runs providence.

Earlier in his career, he was General Manager for Network and Service Management at Cisco, where he was recruited to run the business during its transition to becoming a public company during the Dot Com craze. He also served as the CEO of American Internet, which was acquired by Cisco.


Brennan holds a B.A. in Psychology from Manhattan College. While he enjoys stereotypical leisure pursuits, he’s not any good at them, so he spends his time focused on helping people who ask for his help. He and his wife, Andrea, live in Sherborn with their dog, Desi, and are grateful that their two adult sons live in the area.