The Customer UnSuccess Podcast
By Joe Di Grande
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Episodes: 29
Description
Tired of Customer Success conversations that sound like they were written by a vendor's PR team?
The Customer [Un]Success Podcast cuts through the noise to expose what’s actually broken in Customer Success, and other GTM roles, and what to do about it. Hosted by Joe Di Grande, a digital CS, Tech Touch, and RevOps leader with experience at companies like Business Insider, Ceros, and eMarketer, this podcast brings raw, unfiltered conversations with post-sale leaders who’ve been in the trenches.
We talk about what happens when CS playbooks fail, when sales overpromises, and when retention depends on more than just relationships. Each episode dives into real-world stories, honest mistakes, and tactical strategies to fix what’s broken from scaling with automation to aligning cross-functional teams, driving NRR, and surviving in today’s efficiency-first SaaS world.
Whether you’re in CS, CX, RevOps, or GTM, this is the podcast for people who are done pretending everything’s fine.
| Episode | Date |
|---|---|
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How To Win Over The C‑Suite and Turn Champions Into Heroes w/ Rachel Provan CEO of Provan Success
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Apr 06, 2026 |
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Stop People-Pleasing, Start Outcome-Pleasing w/ Jess Szivos VP of Customer Success at Invisory
|
Mar 23, 2026 |
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Chaos Threshold: Startup CS Vs Enterprise w/ Maranda Dziekonski Chief Customer Officer at Fexa
|
Mar 09, 2026 |
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From Surprise Non-Renewal To Sales-CS Alignment w/ Guy Galon Chief CS & Revenue Leader at Obrela
|
Feb 23, 2026 |
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The True Cost Of A Bad-Fit Customer And How To Walk Away w/ Shari Srebnick
|
Feb 09, 2026 |
|
Saying Yes Too Much Hurts Results w/ Lindsey LeFaivre VP of Customer Success at AchieveIt
|
Jan 26, 2026 |
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How We Turn Angry Clients Into Loyal Advocates w/ Rob Zambito CEO of Success Scaled Consulting
|
Jan 12, 2026 |
|
Digital CS, Done The Hard Way w/ Madelyn DePrey Global VP of Customer Success @ Aircall
|
Oct 20, 2025 |
|
From Fake Leads to Firm Ethics: Rebuilding Trust w/ Jerry Van Vort VP of CS @WUWTA
|
Oct 06, 2025 |
|
Leading Without a Playbook w/ Stephanie Blair
|
Sep 29, 2025 |
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The Silent Competitor: How One Client Deployed a Rival Solution Under the Radar w/ Kristi Faltorusso
|
Sep 22, 2025 |
|
From Farmhouse Tables to Digital Community: An Entrepreneur's Journey w/ Brad Davis of Success Panda
|
Sep 15, 2025 |
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Rescue Stories: The Hidden Dangers of CS Heroics w/ Greg Daines CEO @ ChurnRX
|
Sep 08, 2025 |
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Scaling Office Hours: The Art of Failing Fast w/ Kat Breeggemann Founder of Katalyst CX
|
Sep 01, 2025 |
|
Navigating C-Suite Personalities: A CSM's Survival Guide w/ Tiffany Parkes from User Interviews
|
Aug 25, 2025 |
|
Beyond the Money Ask: Building Customer Engagement for Successful Renewals w/ Marie Lunney
|
Aug 18, 2025 |
|
The Helicopter CCO: Breaking Silos & Building Trust w/ Anthony DeShazor
|
Aug 12, 2025 |
|
The Trust Tightrope: Rebuilding Customer Confidence After a Misstep w/ Kevin Metzger
|
Aug 04, 2025 |
|
Intensity and Professionalism: The Keys to Implementation Success w/ Sri Ganesan
|
Jul 28, 2025 |
|
When Your Data Structure Derails Digital Customer Success w/ Aaron Hatton
|
Jul 21, 2025 |
|
Your Go-To-Market Teams Are Speaking Different Languages w/ Camela Thompson
|
Jul 14, 2025 |
|
Building Customer Experience that Drives Business Value w/ Andrew Carothers from Cisco
|
Jul 07, 2025 |
|
Shiny Objects Don't Solve Problems: A Honest Look at CS Technology w/ Sally Stoewe
|
Jun 30, 2025 |
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Happy Isn't Enough: Why Satisfied Customers Still Churn w/ Alex Glick from Outreach.io
|
Jun 16, 2025 |
|
Hidden Pitfalls of CS Platform Implementations w/ Marley Wagner, EverHealth
|
Jun 09, 2025 |
|
Saving the $2.2 Million Deal w/ De'Edra Williams from DeepHow
|
Jun 02, 2025 |
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Beyond Relationships: What Really Prevents Churn w/ Justin Chappell
|
May 26, 2025 |
|
Default to Action: Why Your First Try Will Probably Fail - w/ Dillon Young
|
May 20, 2025 |
|
Customer [Un]Success - Teaser
|
May 09, 2025 |