Profile
Garrett is a senior Customer Success executive with more than 15 years of experience leading high-impact post-sales operations, digital transformation, and enterprise customer engagement across SaaS, cybersecurity, and managed services. He combines deep technical fluency with strategic vision to help organizations improve retention, reduce churn, and align customer outcomes with business value. A builder at heart, Garrett is known for scaling high-performing CS teams, optimizing platforms like Gainsight and Salesforce, and leading through complexity in regulated, mission-critical environments.
Professional Background
Prior, Garrett was the Director of Enterprise Customer Success at Rapid7, where he led a $350M ARR portfolio and a team of 60+ CSMs across key verticals, including healthcare, finance, and technology. There, he increased SaaS cloud security retention by 46%, integrated tools like Gainsight and Gong, and drove enterprise-wide CS transformation efforts. Before that, he held senior roles at NaviSite, the Center for Health Information & Analysis, and CenturyLink, where he built scalable CS frameworks, led large-scale IT transformations, and managed regional P&Ls supporting over $100M in ARR. Garrett began his career as a network engineer supporting enterprise clients at IBM and Partners Healthcare, laying the technical foundation for his later leadership in service delivery and customer operations.
Education
Garrett has a Bachelor of Arts in Political Science from Boston College. He is ITIL v3 Foundation–certified and has completed executive programs in cybersecurity at MIT Sloan.
Furthermore
Garrett is a passionate explorer, whether he’s completing the Sydney Harbor Bridge Climb (despite his fear of heights), cage-diving with sharks off Hawaii (much to his family’s horror), or discovering hidden gems throughout New England. He’s always up for a new experience and meeting interesting people along the way. When he’s back on dry land, you’ll find him at live music shows, and he owns more concert shirts than he cares to admit.