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The Customer UnSuccess Podcast
Joe Di Grande
22 episodes
2 weeks ago
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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Business
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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 •...
Show more...
Business
Episodes (20/22)
The Customer UnSuccess Podcast
Digital CS, Done The Hard Way w/ Madelyn DePrey Global VP of Customer Success @ Aircall
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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2 weeks ago
37 minutes

The Customer UnSuccess Podcast
From Fake Leads to Firm Ethics: Rebuilding Trust w/ Jerry Van Vort VP of CS @WUWTA
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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1 month ago
43 minutes

The Customer UnSuccess Podcast
Leading Without a Playbook w/ Stephanie Blair
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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1 month ago
35 minutes

The Customer UnSuccess Podcast
The Silent Competitor: How One Client Deployed a Rival Solution Under the Radar w/ Kristi Faltorusso
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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1 month ago
38 minutes

The Customer UnSuccess Podcast
From Farmhouse Tables to Digital Community: An Entrepreneur's Journey w/ Brad Davis of Success Panda
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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1 month ago
46 minutes

The Customer UnSuccess Podcast
Rescue Stories: The Hidden Dangers of CS Heroics w/ Greg Daines CEO @ ChurnRX
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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2 months ago
53 minutes

The Customer UnSuccess Podcast
Scaling Office Hours: The Art of Failing Fast w/ Kat Breeggemann Founder of Katalyst CX
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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2 months ago
30 minutes

The Customer UnSuccess Podcast
Navigating C-Suite Personalities: A CSM's Survival Guide w/ Tiffany Parkes from User Interviews
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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2 months ago
42 minutes

The Customer UnSuccess Podcast
Beyond the Money Ask: Building Customer Engagement for Successful Renewals w/ Marie Lunney
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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2 months ago
45 minutes

The Customer UnSuccess Podcast
The Helicopter CCO: Breaking Silos & Building Trust w/ Anthony DeShazor
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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2 months ago
49 minutes

The Customer UnSuccess Podcast
The Trust Tightrope: Rebuilding Customer Confidence After a Misstep w/ Kevin Metzger
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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3 months ago
39 minutes

The Customer UnSuccess Podcast
Intensity and Professionalism: The Keys to Implementation Success w/ Sri Ganesan
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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3 months ago
44 minutes

The Customer UnSuccess Podcast
When Your Data Structure Derails Digital Customer Success w/ Aaron Hatton
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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3 months ago
42 minutes

The Customer UnSuccess Podcast
Your Go-To-Market Teams Are Speaking Different Languages w/ Camela Thompson
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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3 months ago
37 minutes

The Customer UnSuccess Podcast
Building Customer Experience that Drives Business Value w/ Andrew Carothers from Cisco
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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4 months ago
45 minutes

The Customer UnSuccess Podcast
Shiny Objects Don't Solve Problems: A Honest Look at CS Technology w/ Sally Stoewe
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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4 months ago
45 minutes

The Customer UnSuccess Podcast
Happy Isn't Enough: Why Satisfied Customers Still Churn w/ Alex Glick from Outreach.io
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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4 months ago
41 minutes

The Customer UnSuccess Podcast
Hidden Pitfalls of CS Platform Implementations w/ Marley Wagner, EverHealth
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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5 months ago
36 minutes

The Customer UnSuccess Podcast
Saving the $2.2 Million Deal w/ De'Edra Williams from DeepHow
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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5 months ago
38 minutes

The Customer UnSuccess Podcast
Beyond Relationships: What Really Prevents Churn w/ Justin Chappell
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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5 months ago
31 minutes

The Customer UnSuccess Podcast
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 •...