Mike O'Brien is a digital government and AI transformation executive with over 20 years of experience driving P&L growth, client relationships, and large-scale modernization programs across Federal, State, and Local government.

As a Principal at Thoughtworks, Mike leads the State, Local and Education practice, serving as a trusted advisor to government and higher education CIOs, CTOs, and leadership on AI-first transformation strategies, cloud modernization roadmaps, and data platform architecture. In his first year, he built a $5B+ strategic pipeline and closed $20M in AI and digital modernization engagements — exceeding forecast by 30%. He authored “The Composable Agency,” a comprehensive thought leadership framework defining a new blueprint for autonomous public service, and scaled the Seamless Government Experience (SGX) platform in partnership with Google Cloud.

Prior to Thoughtworks, Mike served as Vice President at SMX (Smartronix), where he held full P&L ownership for a $160M/year division serving Federal and State clients. He captured over $500M in contract awards, grew the Commonwealth of Massachusetts account from $3M to $55M annually (1,730% growth), and led the largest cloud migration in Massachusetts history — the Healthcare Insurance Exchange implementation.

Earlier in his career, Mike held leadership positions at Clearpath Solutions Group, where he increased services and cloud revenue 300% and helped drive a successful PE acquisition by TH Lee; at Aquilent, where he won a $100M GSA Cloud Services BPA and achieved AWS Premier Partnership; and at Smartronix, where he captured major Federal deals including a 10-year MSA at the Federal Reserve. He started his career at AOL in 1996, where he was promoted nine times over 14 years to Technical Director leading a 100+ person global IT infrastructure organization.

Mike is also the founder of PropelAI, an AI-powered proposal generation platform for government contractors built on the APMP-aligned capture methodology, achieving 95%+ compliance requirement extraction and 87/100 quality scores on autonomous generation.

Mike lives in Purcellville, Virginia with his wife Megan and their sons John and Sam. When he's not working, you'll find him on the golf course, out on the water fishing and boating from his second home on the Little Wicomico River in Reedville, Virginia, or in the kitchen experimenting with a new recipe.