In this episode, Dannah Vaughan joins me for a grounded conversation about customer success, post-sales execution, and the real cost of losing the human touch in an increasingly automated world.
We explore why onboarding has improved while support continues to fail customers, how health scores should guide curiosity rather than dictate decisions, and why legacy customers demand real relationships, not automation. We also talk candidly about short CS leadership tenures, layoffs in tech, and the resilience required to keep building when the rules keep changing.
This is a practical, human-first look at what actually drives retention and expansion when tools, dashboards, and AI can only take you so far.
Episode Chapters
01:08 — Introduction
03:35 — Where post-sales promises meet reality
05:46 — Telecom lessons and the disappearing human
07:34 — The reality of AI, Automation, and the human element
13:37 — Where we really are with AI, is it a “toddler?”
17:56 — Dashboards, health scores, and seeing risk sooner
29:21 — Customer Success under CROs and what gets undervalued
35:59 — The avocado rotary phone and technology that still works!
39:54 — Career myth debunking
41:31 — Does It Hold Water?
45:54 — Chip Shots
Book Recommendation
Never Split the Difference: Negotiating As If Your Life Depended On It―Unlock Your Persuasion Potential in Professional and Personal Life by Chris Voss
Connect with Guest
LinkedIn: https://www.linkedin.com/in/dannahvaughan/
Website: https://rebelsofSaaS.com
Also mentioned on the show:
Podcast: Rebels of SaaS
🔗 Connect with Gary Marra:
· LinkedIn: https://www.linkedin.com/in/gary-marra/
· Marra CX Hub: https://marracxhub.com/
· YouTube: YCYS YouTube Page
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