February 20, 2026
Why Onboarding Kills SaaS Retention

Sam Chlebowski, co-founder of LaunchBay, joined Jenny Vo on The SaaS Playbook for "Your Onboarding Is Killing Retention: The Post-Sale System SaaS Teams Keep Ignoring."
Jenny and Sam dig into why most SaaS companies lose customers before they ever see real value, and why the culprit usually isn't the product. Sam shares lessons from scaling client onboarding at Brighter Vision, four warning signs that an onboarding system is breaking, and why hiring more CSMs doesn't fix a systems problem.
The conversation also covers how onboarding shapes retention, referrals, and expansion, the differences between US and Australian SaaS adoption, and the North Star metric LaunchBay tracks internally to keep onboarding on track as a company scales.
Where to watch:
About the host
Jenny Vo hosts The SaaS Playbook, a podcast for B2B SaaS founders, operators, and growth leaders covering GTM strategy, leadership, product development, AI adoption, and customer success. She's also the founder of Hera Digital, an AI-driven sales automation agency for B2B software and service companies.


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