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 ...
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Joe Di Grande Podcasts

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The Silent Competitor: How One Client Deployed a Rival Solution Under the Radar w/ Kristi Faltorusso
38:50
38:50
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38:50The 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 awareness to avoid being blindsided at renewal time. • Competitors view your customers as prime targets since they've already secured budg…
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From Farmhouse Tables to Digital Community: An Entrepreneur's Journey w/ Brad Davis of Success Panda
46:23
46:23
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46:23Brad 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. • Brad's entrepreneurial journey began with Cincinnati Farmhouse Tables, teaching him valuable business lessons • Success Panda was …
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Rescue Stories: The Hidden Dangers of CS Heroics w/ Greg Daines CEO @ ChurnRX
53:35
53:35
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53:35Greg 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 CS culture but indicate systemic failures and rarely result in long-term retention • Data shows zero correlation between customer s…
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Scaling Office Hours: The Art of Failing Fast w/ Kat Breeggemann Founder of Katalyst CX
30:37
30:37
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30:37Kat 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 open to all customers regardless of size or segment • Themed office hours failed because customers joined whichever session was hap…
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Navigating C-Suite Personalities: A CSM's Survival Guide w/ Tiffany Parkes from User Interviews
42:25
42:25
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42:25Tiffany 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. The conversation explores the challenging journey of transitioning from mid-market to strategic CSM roles and the importance of …
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Beyond the Money Ask: Building Customer Engagement for Successful Renewals w/ Marie Lunney
45:11
45:11
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45:11Marie 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 importance of aligning executives around customer success, creating internal workflows before customer-facing automation, and remembe…
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1
The Helicopter CCO: Breaking Silos & Building Trust w/ Anthony DeShazor
49:32
49:32
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49:32Anthony 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 journey from gatekeeping to enabling teams through a mindset shift from "No" to "Yes, and" thinking. • Taking customer ownership t…
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The Trust Tightrope: Rebuilding Customer Confidence After a Misstep w/ Kevin Metzger
39:24
39:24
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39:24Communication 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 with an enterprise client. • Customer's SSL certificate expired causing application issues • According to contracts, certificate rene…
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Intensity and Professionalism: The Keys to Implementation Success w/ Sri Ganesan
44:12
44:12
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44:12Sri 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 expectations, improving communication, and catching issues before they become dealbreakers. • Intensity means the ball is always in your cour…
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1
When Your Data Structure Derails Digital Customer Success w/ Aaron Hatton
42:30
42:30
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42:30Aaron 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 importance of cross-functional collaboration when establishing digital customer success programs and the challenges of defining who your cu…
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1
Your Go-To-Market Teams Are Speaking Different Languages w/ Camela Thompson
37:53
37:53
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37:53Camela Thompson, Head of Marketing at RevOps Co-op and co-host of the RevOps AF podcast, shares how a major analytics implementation nearly collapsed when the focus shifted from customer value to delivery timelines. • Different definitions of attribution lead to misalignment in go-to-market analytics implementations • Standard onboarding metrics of…
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1
Building Customer Experience that Drives Business Value w/ Andrew Carothers from Cisco
45:51
45:51
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45:51Data access is the fuel for customer experience initiatives and was a three-year battle at Cisco, requiring persistent effort to overcome departmental silos. Andrew Carruthers shares insights from his 17 years at Cisco, where he led digital CX strategy during their transition from hardware to software. • Lack of corporate mandate for the CS functio…
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Shiny Objects Don't Solve Problems: A Honest Look at CS Technology w/ Sally Stoewe
45:50
45:50
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45:50Sally from Customer Obsessing Consulting shares insights on why CS technology implementations fail despite good intentions and how teams can better prepare for new tools. • Every tech company uses between 57-110 tools, creating significant tech sprawl challenges • Project management capabilities are crucial but undervalued skills for CSMs handling …
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1
Happy Isn't Enough: Why Satisfied Customers Still Churn w/ Alex Glick from Outreach.io
41:46
41:46
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41:46Customer satisfaction doesn't guarantee retention, and challenging conversations are often essential for genuine success. Strategic CSM from Outreach.io, Alex Glick shares his experiences losing an enterprise account just months into a role and how it reshaped his entire approach to customer success. • Happy customers still churn when they don't se…
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1
Hidden Pitfalls of CS Platform Implementations w/ Marley Wagner, EverHealth
36:45
36:45
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36:45Marlee Wagner, Head of Customer Success Programs & Strategy at EverHealth, shares a cautionary tale about a failed CS platform implementation due to overlooked data infrastructure incompatibilities, and provides crucial advice for evaluating customer success platforms. • Carefully examine your data infrastructure compatibility when evaluating new p…
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1
Saving the $2.2 Million Deal w/ De'Edra Williams from DeepHow
38:54
38:54
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38:54De' Edra Williams, Chief Customer Officer of DeepHow, shares how her team turned a potential $2.2 million customer churn into a full renewal with expansion by mobilizing cross-functional resources and developing a strategic intervention plan. This customer success recovery story demonstrates the importance of proactive renewal planning, deep custom…
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1
Beyond Relationships: What Really Prevents Churn w/ Justin Chappell
31:48
31:48
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31:48Customer success isn't just about building relationships – it's about understanding your customers' strategic outcomes and helping them achieve measurable business results. • Building relationships without connecting to business outcomes leaves accounts vulnerable to churn • Track customer data meaningfully and use it in authentic, non-cheesy ways …
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1
Default to Action: Why Your First Try Will Probably Fail - w/ Dillon Young
41:57
41:57
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41:57What happens when leadership doesn't understand the fundamental differences between customer success and sales? Dillon Young, founder of Lifetime Value Media and host of the Daily Stand-Up podcast, shares hard-won wisdom from 15 years in customer success on this revealing episode of Customer Unsuccess. At the heart of many CS struggles is a critica…
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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…
…
continue reading