Customer Success, Automation, and the Cost of Losing the Human Touch with Dannah Vaughan
Wed Jan 21 2026
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 Chapters01:08 — 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 RecommendationNever 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 GuestLinkedIn: 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
📣 🎧 Please Listen & Subscribe
💡 Don’t forget to subscribe and leave a review if you enjoyed the episode!
👉 Follow Your Customer, Your Success for more insights on customer experience, leadership, and business strategy.
Want to be a guest on Your Customer, Your Success?
Send Gary Marra a message on PodMatch here:
https://www.podmatch.com/hostdetailpreview/1726154102094403cb5558fc4
#CX #CustomerSuccess #ClientExperience #Leadership #FractionalLeadership #GrowthStrategy #TeamAlignment #Podcast #BusinessLeadership #CustomerExperience
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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 Chapters01:08 — 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 RecommendationNever 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 GuestLinkedIn: 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 📣 🎧 Please Listen & Subscribe 💡 Don’t forget to subscribe and leave a review if you enjoyed the episode! 👉 Follow Your Customer, Your Success for more insights on customer experience, leadership, and business strategy. Want to be a guest on Your Customer, Your Success? Send Gary Marra a message on PodMatch here: https://www.podmatch.com/hostdetailpreview/1726154102094403cb5558fc4 #CX #CustomerSuccess #ClientExperience #Leadership #FractionalLeadership #GrowthStrategy #TeamAlignment #Podcast #BusinessLeadership #CustomerExperience