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Hosted by Joe Di Grande · 🇺🇸 US · EN-US · 29 episodes
Established thought leaders with verified media credentials.
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 everyth
Joe Di Grande hosts The Customer UnSuccess Podcast, a business show with 29 episodes published.
We explore how to build customer success from scratch and make it visible to executives by speaking in outcomes, not activities. We lean on psychology to drive adoption, create champions, and pre‑pave ethical expansions
We unpack why generic 30-60-90 plans fall flat and how to turn them into customer coauthored blueprints tied to KPIs. Jess shares therapist-grade discovery tactics, persona-aware messaging, and how data plus boundaries c
We compare enterprise customer success with early-stage startup CS and get honest about chaos tolerance, ambiguity, politics, and fit. Maranda shares hiring exercises, interview tactics, and career moves that protect you
We unpack a “sure thing” renewal that fell apart, the hidden decision makers who swung the outcome, and why quiet QBRs signal danger. We also break down a high-stakes implementation sold ahead of product readiness and ho
We trace a marquee deal that imploded at handoff, then rebuild the path from close to value with practical fixes for alignment, multithreading, and fit. Along the way, we count the real cost to serve and explain why some
We unpack how saying yes too fast derails outcomes and how visible boundaries make better teams. Lindsey LeFaivre shares hard-won lessons from a 1,500-branching workflow misfire to a delivery-room out-of-office, turning
We trade war stories from diner counters and real estate closings to show how psychology, better playbooks, and value-add concessions defuse escalations and protect renewals. Rob shares Feel–Felt–Found, digital cancellat
We dig into how moving 70% of SMB customers from named CSMs to a pooled digital model exposed misaligned expectations created during sales and trial. We reframe scaled CS to start at acquisition, tie product to retention
We trace how a CS leader uncovered a flood of fake leads, rebuilt guardrails under investor pressure, and chose ethics over easy money—then connect those lessons to hiring, tooling, and scaling without losing the plot. T
Stephanie Blair, founder and CEO of Know and Flourish, shares profound insights from her experience leading sales and customer success teams across the US and UK. Her stories reveal how understanding each team member's u
The competitive landscape in SaaS is ruthless, with rivals actively targeting your existing customers who already have budget allocated and pain points identified. Customer Success teams must develop competitive awarenes
Brad Davis shares how your professional network directly correlates with career success in customer success, emphasizing that careers are team sports requiring consistent engagement rather than last-minute networking. •
Greg Daines, CEO of ChurnRx, exposes why heroic customer rescues are actually disaster stories and how focusing on customer satisfaction is often counterproductive to retention. • Rescue stories are often celebrated in C
Kat Brigham shares how SalesLoft's daily office hours program evolved from themed sessions to open forums, revealing that customers prefer flexibility over structure when seeking help. • Started with daily office hours o
Tiffany Parks shares her soul-crushing experience of having her carefully prepared loyalty program presentation dismissed as "boilerplate" by a CEO after working for three weeks on what she thought was a bespoke strategy
Marie Lunney shares insights from her experience building digital customer success programs, highlighting the pitfalls of focusing only on renewals rather than designing a complete customer journey. She discusses the imp
Anthony DeShazer shares how his protective approach to customer management earned him the reputation as "The VP of No" and how he transformed his leadership style to foster cross-functional collaboration. He reveals the
Communication in customer success hinges not on what you say, but what your customer hears, as Kevin Metzger discovered when a casual comment about contractual obligations spiraled into a three-month recovery process wit
Sri Ganesan shares how bringing intensity and professionalism to implementation projects can dramatically improve customer partnerships and outcomes. The RocketLane CEO details specific strategies for setting expectation
Aaron Hatton, digital CS program builder at PV Case, shares how parent-child account relationships in data infrastructure nearly derailed a customer success platform rollout. His experience reveals the critical importanc
Rachel Provan
Top 25 Customer Success Leader in the U.S, brain-based leadership coach · Provan Success
1 appearance on this show
Maranda Dziekonski
Senior Vice President of Customer Success · Datasembly
1 appearance on this show
Brad Davis
former MLS pro and US Men’s National Team player · United Methodist Church
1 appearance on this show
Sri Ganesan
co-founder and CEO · Freshworks
1 appearance on this show
Jess Szivos
Invisory
1 appearance on this show
Guy Galon
Obrela
1 appearance on this show
Lindsey LeFaivre
AchieveIt
1 appearance on this show
Rob Zambito
Success Scaled Consulting
1 appearance on this show
Madelyn DePrey
Aircall
1 appearance on this show
Jerry Van Vort
WUWTA
1 appearance on this show
Stephanie Blair
Know and Flourish
1 appearance on this show
Greg Daines
ChurnRX
1 appearance on this show
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The Customer UnSuccess Podcast is hosted by Joe Di Grande. The show is categorised under business and has published 29 episodes.
The Customer UnSuccess Podcast has published 29 episodes.
The Customer UnSuccess Podcast regularly covers business. It sits in the business category.
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Episodes of The Customer UnSuccess Podcast average 43 minutes. a focused format where a clear narrative arc and tight preparation matter most.
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