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PODCAST

The Customer UnSuccess Podcast

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

business

All Episodes

37:05

Digital CS, Done The Hard Way w/ Madelyn DePrey...

The Customer UnSuccess Podcast ·

2025/10/20

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, and use enrichment and scoring to focus human effort. • abrupt shift from named CSMs to pooled model for SMBs • misaligned sales promises creating a broken handoff • product-led trial design to reduce high-touch conversion • capturing use cases and goals during onboarding •...

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43:50

From Fake Leads to Firm Ethics: Rebuilding Trust w/...

The Customer UnSuccess Podcast ·

2025/10/06

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. The stories move from legal lead ops to cannabis lab testing, all through the lens of trust and customer value. • discovering affiliate-driven fake leads and broken credit policies • installing KPIs, tools, and training in a headless CS org • pushing product safeguards and par...

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35:54

Leading Without a Playbook w/ Stephanie Blair

The Customer UnSuccess Podcast ·

2025/09/29

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 unique motivations and adapting leadership styles across different cultural contexts can transform team performance. 🎙️ Guest: Stephanie Blair 📣 Find Stephanie: LinkedIn: https://www.linkedin.com/in/blairstephanie/ Know & Flourish: https://www.knowandflourish...

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38:50

The Silent Competitor: How One Client Deployed a...

The Customer UnSuccess Podcast ·

2025/09/22

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 awareness to avoid being blindsided at renewal time. • Competitors view your customers as prime targets since they've already secured budget and demonstrated willingness to invest • CSMs often operate with less competitive awareness than sales teams, leaving them vulnerable to blinds...

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46:23

From Farmhouse Tables to Digital Community: An...

The Customer UnSuccess Podcast ·

2025/09/15

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. • Brad's entrepreneurial journey began with Cincinnati Farmhouse Tables, teaching him valuable business lessons • Success Panda was born from identifying the need for centralized CS resources and meaningful professional connections • The platform uses a $2-$4 microtransaction m...

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53:35

Rescue Stories: The Hidden Dangers of CS Heroics w/...

The Customer UnSuccess Podcast ·

2025/09/08

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 CS culture but indicate systemic failures and rarely result in long-term retention • Data shows zero correlation between customer satisfaction and retention—happy customers leave at the same rate as unhappy ones • Customers who experience problems actually stay more than twice...

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30:37

Scaling Office Hours: The Art of Failing Fast w/ Kat...

The Customer UnSuccess Podcast ·

2025/09/01

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 open to all customers regardless of size or segment • Themed office hours failed because customers joined whichever session was happening soonest • Scaled to 13 weekly sessions across global time zones to accommodate customers worldwide • Tracked attendance data through Zoom-S...

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42:25

Navigating C-Suite Personalities: A CSM's Survival...

The Customer UnSuccess Podcast ·

2025/08/25

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. The conversation explores the challenging journey of transitioning from mid-market to strategic CSM roles and the importance of navigating different personality types. • Making the jump from mid-market to strategic CSM while changing companies creates unique challenges • De...

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45:11

Beyond the Money Ask: Building Customer Engagement...

The Customer UnSuccess Podcast ·

2025/08/18

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 importance of aligning executives around customer success, creating internal workflows before customer-facing automation, and remembering that meaningful engagement requires multiple touchpoints throughout the customer lifecycle. • Focusing exclusively on renewal automation can ...

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49:32

The Helicopter CCO: Breaking Silos & Building Trust...

The Customer UnSuccess Podcast ·

2025/08/12

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 journey from gatekeeping to enabling teams through a mindset shift from "No" to "Yes, and" thinking. • Taking customer ownership to harmful extremes created organizational friction • Solving customer confusion by requiring all teams to get "passports" to customer land • Shift...

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39:24

The Trust Tightrope: Rebuilding Customer Confidence...

The Customer UnSuccess Podcast ·

2025/08/04

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 with an enterprise client. • Customer's SSL certificate expired causing application issues • According to contracts, certificate renewal was customer's responsibility • Kevin's off-the-cuff remark about contract terms damaged relationship • Previously excellent customer service ...

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44:12

Intensity and Professionalism: The Keys to...

The Customer UnSuccess Podcast ·

2025/07/28

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 expectations, improving communication, and catching issues before they become dealbreakers. • Intensity means the ball is always in your court - never waiting on customers without following up • Catch problems early through milestone-based CSAT surveys to identify even "three-star" expe...

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42:30

When Your Data Structure Derails Digital Customer...

The Customer UnSuccess Podcast ·

2025/07/21

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 importance of cross-functional collaboration when establishing digital customer success programs and the challenges of defining who your customer truly is. • Working with complex data structures where the entity paying for software differs from the entity using it • Importance of invo...

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37:53

Your Go-To-Market Teams Are Speaking Different...

The Customer UnSuccess Podcast ·

2025/07/14

Camela 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 often focus on internal KPIs rather than achieving customer objectives • Alignment between marketing, sales, and other departments is crucial for an...

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45:51

Building Customer Experience that Drives Business...

The Customer UnSuccess Podcast ·

2025/07/07

Data 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 function created alignment challenges • Getting access to customer data took three years due to departmental silos • The most effective approach was focu...

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45:50

Shiny Objects Don't Solve Problems: A Honest Look at...

The Customer UnSuccess Podcast ·

2025/06/30

Sally 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 customer journeys • Many organizations purchase tools without proper data readiness or team alignment • Implementation timelines and resource requ...

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41:46

Happy Isn't Enough: Why Satisfied Customers Still...

The Customer UnSuccess Podcast ·

2025/06/16

Customer 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 see ROI, while frustrated customers might renew if they recognize business value • Success plans are only valuable when continuously referenced and ...

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36:45

Hidden Pitfalls of CS Platform Implementations w/...

The Customer UnSuccess Podcast ·

2025/06/09

Marlee 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 platforms • Involve RevOps early in platform evaluations to avoid technical mismatches • Consider three critical data aspects: validity, access...

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38:54

Saving the $2.2 Million Deal w/ De'Edra Williams from...

The Customer UnSuccess Podcast ·

2025/06/02

De' 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 customer listening, and aligning solutions with specific business outcomes. • Building a rigorous renewal process that starts 6-12 months before contrac...

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31:48

Beyond Relationships: What Really Prevents Churn w/...

The Customer UnSuccess Podcast ·

2025/05/26

Customer 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 to strengthen connections • Ensure smooth information transfer from sales to implementation to customer success • Multi-thread relationships withi...

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22 results

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