S1E2: Scaling Customer Success from $1M to $300M+ ARR w/ John Gleeson The Leen Playbook

John Gleeson is the Managing Partner of Success VP, a pre-seed and seed-stage focused fund that invests and supports founders with their post sales journey. John is a leader within the post-sales world. He served as the Vice President of Customer Success at Motive Inc. (Series F) where for over five years he led his team through incredible hyper-growth, from less than $1 Million in ARR to over $300 Million, serving over 130,000 customers, supporting a team of 150 and creating nearly 3 Billion in Enterprise Value. Prior to Motive, John was the first hire at Affinio where he built the first Sales function before leading Customer Success.

Episode Notes:


How does John define Customer Success (2:22)
Unraveling the path from Head of Customer Success to VP of Customer Success (5:30)
Scaling Customer Success within a hyper-growth startup: From $1M to over $300M (14:44)
Measuring the impact of Customer Success (23:03)
Insider Insights: Best Practices from John's journey in scaling Customer Success (30:14)
Examining Post-Sales trends through the lens of an venture capitalist (35:00)