

The Customer UnSuccess Podcast
Joe Di Grande
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.
Episodes
Mentioned books

Jul 14, 2025 • 38min
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 analytics implementation success• True value comes from adapting to customer needs rather than standardizing implementations• The human element often derails data projects - even with solid analytics, decisions are influenced by feelings• Cross-functional collaboration is essential but challenging when different teams have competing metrics• Documentation of data definitions and governance prevents misalignment between departments• Soft skills like communication and empathy are as critical as technical skills in operations roles🎙️ Guest:Camela Thompson – Head of Marketing at RevOps Co-op and Co-host of the RevOps AF podcast https://www.linkedin.com/in/camela-thompson/ 🏢 Communities:RevOps Co-op –https://www.revopscoop.com/ 📚 Books & Frameworks:Nonviolent Communication by Marshall Rosenberg – https://amzn.to/4lN1CdJMindset by Dr. Carol Dweck – https://amzn.to/4kxBPVK🎧 Podcasts:RevOps AF – Co-hosted by Camela, https://www.revopscoop.com/learn/podcast🌐 Website https://www.joedoestechtouch.com/📰 Subscribe to the JDTT Newsletter – Get raw insights, no-fluff frameworks, and tech touch tactics straight to your inbox: https://www.joedoestechtouch.com/jdttnewsletter 🎙️ Be a Guest on the Podcast Have a CS horror story or digital-first strategy worth sharing? Submit to be a guest:https://www.joedoestechtouch.com/podcast 🔗 Connect with Joe on LinkedIn https://www.linkedin.com/in/josephdigrande📺 Watch Full Episodes on YouTube: https://www.youtube.com/channel/UCaH58ojbaWym4ej_PedQ4Fw_______________________________Tools:Logitech Creators Blue Yeti USB Microphone: https://amzn.to/4nHOFDNLogitech Brio 4K Webcam: https://amzn.to/3GtKsmxSony WH-1000XM4 Noise Cancelling Wireless Headphones: https://amzn.to/44Q0xv4Apple 2024 MacBook Pro Laptop: https://amzn.to/4lH6u3W

Jul 7, 2025 • 46min
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 focusing on business metrics rather than satisfaction scores• Low renewal rates were solved by simply notifying customers about contract expirations• Creating a separate CRM system was a mistake that created additional silos• Customer experience should be positioned as a growth engine, not just satisfaction• Adoption is critical to prevent products from being cut during tech stack consolidations• With Gen AI, they expanded localization to reach new markets like Arabic-speaking customers• Consistency in experience matters more than occasional "surprise and delight" moments• Experience is often the primary reason customers leave, not product functionalityFollow Andrew Carothers: https://www.linkedin.com/in/andrew-carothers/Shoutouts:Digital Hesitation by JB Wood & Thomas Lah (TSIA) – Book recommendation by Andrew; outlines how to operationalize digital customer experienceDigital Customer Success Podcast — https://digitalcustomersuccess.com/CX Passport Podcast –https://www.cxpassport.com/🌐 Website https://www.joedoestechtouch.com/📰 Subscribe to the JDTT Newsletter – Get raw insights, no-fluff frameworks, and tech touch tactics straight to your inbox: https://www.joedoestechtouch.com/jdttnewsletter 🎙️ Be a Guest on the Podcast Have a CS horror story or digital-first strategy worth sharing? Submit to be a guest:https://www.joedoestechtouch.com/podcast 🔗 Connect with Joe on LinkedIn https://www.linkedin.com/in/josephdigrande📺 Watch Full Episodes on YouTube: https://www.youtube.com/channel/UCaH58ojbaWym4ej_PedQ4Fw_______________________________Tools:Logitech Creators Blue Yeti USB Microphone: https://amzn.to/4nHOFDNLogitech Brio 4K Webcam: https://amzn.to/3GtKsmxSony WH-1000XM4 Noise Cancelling Wireless Headphones: https://amzn.to/44Q0xv4Apple 2024 MacBook Pro Laptop: https://amzn.to/4lH6u3W

Jun 30, 2025 • 46min
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 requirements are often underestimated during the buying process• Account hierarchy inconsistencies between CRM, CS platforms, and billing systems create major integration problems• Health scores can be misleading when definitions aren't aligned across teams• AI tools like ChatGPT can help CSMs work more efficiently with existing systems before investing in new platforms• CSPs should participate in defining use cases and personas before implementation begins• Involving individual contributors in tool selection creates better buy-in and practical solutions• Examining capabilities of existing tools often reveals untapped potential that solves immediate problemsStart with the tools you already have and fully understand their capabilities before purchasing new solutions. Involve your team in the process, and only invest in new technology when you're actually ready for implementation.Follow Sally on LinkedIn: https://www.linkedin.com/in/sallystoewe/Shoutouts:https://www.marijaskobepilley.com/podcasthttps://www.masterclass.com/🌐 Website https://www.joedoestechtouch.com/📰 Subscribe to the JDTT Newsletter – Get raw insights, no-fluff frameworks, and tech touch tactics straight to your inbox: https://www.joedoestechtouch.com/jdttnewsletter 🎙️ Be a Guest on the Podcast Have a CS horror story or digital-first strategy worth sharing? Submit to be a guest:https://www.joedoestechtouch.com/podcast 🔗 Connect with Joe on LinkedIn https://www.linkedin.com/in/josephdigrande📺 Watch Full Episodes on YouTube: https://www.youtube.com/channel/UCaH58ojbaWym4ej_PedQ4Fw_______________________________Tools:Logitech Creators Blue Yeti USB Microphone: https://amzn.to/4nHOFDNLogitech Brio 4K Webcam: https://amzn.to/3GtKsmxSony WH-1000XM4 Noise Cancelling Wireless Headphones: https://amzn.to/44Q0xv4Apple 2024 MacBook Pro Laptop: https://amzn.to/4lH6u3W

Jun 16, 2025 • 42min
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 aligned with business outcomes• Complacency is dangerous especially with enterprise accounts – there is no "ramp time" luxury• Cross-functional relationships and internal political capital critically impact your ability to advocate for customers• Adoption metrics alone don't drive renewals – they must connect to business outcomes executives care about• Building a network of mentors and professional relationships is crucial for career growth in customer success• Challenging leadership assumptions when necessary establishes you as the true voice of the customerFollow Alex on LinkedIn: https://www.linkedin.com/in/alexander-glick/🌐 Website https://www.joedoestechtouch.com/📰 Subscribe to the JDTT Newsletter – Get raw insights, no-fluff frameworks, and tech touch tactics straight to your inbox: https://www.joedoestechtouch.com/jdttnewsletter 🎙️ Be a Guest on the Podcast Have a CS horror story or digital-first strategy worth sharing? Submit to be a guest:https://www.joedoestechtouch.com/podcast 🔗 Connect with Joe on LinkedIn https://www.linkedin.com/in/josephdigrande📺 Watch Full Episodes on YouTube: https://www.youtube.com/channel/UCaH58ojbaWym4ej_PedQ4Fw_______________________________Tools:Logitech Creators Blue Yeti USB Microphone: https://amzn.to/4nHOFDNLogitech Brio 4K Webcam: https://amzn.to/3GtKsmxSony WH-1000XM4 Noise Cancelling Wireless Headphones: https://amzn.to/44Q0xv4Apple 2024 MacBook Pro Laptop: https://amzn.to/4lH6u3W

Jun 9, 2025 • 37min
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, and infrastructure compatibility• Consult with marketing teams who have previously integrated with your CRM• Include the future platform administrators in the decision-making process• Hire administrative talent before finalizing platform selection when possible• Start with small pilot programs when implementing new processes• Build relationships with cross-functional teams to ensure alignmentFollow Marley on LinkedIn: https://www.linkedin.com/in/marleywagner/🌐 Website https://www.joedoestechtouch.com/📰 Subscribe to the JDTT Newsletter – Get raw insights, no-fluff frameworks, and tech touch tactics straight to your inbox: https://www.joedoestechtouch.com/jdttnewsletter 🎙️ Be a Guest on the Podcast Have a CS horror story or digital-first strategy worth sharing? Submit to be a guest:https://www.joedoestechtouch.com/podcast 🔗 Connect with Joe on LinkedIn https://www.linkedin.com/in/josephdigrande📺 Watch Full Episodes on YouTube: https://www.youtube.com/channel/UCaH58ojbaWym4ej_PedQ4Fw_______________________________Tools:Logitech Creators Blue Yeti USB Microphone: https://amzn.to/4nHOFDNLogitech Brio 4K Webcam: https://amzn.to/3GtKsmxSony WH-1000XM4 Noise Cancelling Wireless Headphones: https://amzn.to/44Q0xv4Apple 2024 MacBook Pro Laptop: https://amzn.to/4lH6u3W

Jun 2, 2025 • 39min
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 contract end dates• Implementing a red-yellow-green forecasting system with clear intervention triggers• Mobilizing cross-functional "red teams" for at-risk accounts below 40% renewal probability• Sometimes breaking up with customers is necessary when product-market fit is lacking• Maintaining candor and trust even when parting ways can lead to future opportunities• Customer success must embrace revenue metrics (ARR, NRR, customer lifetime value)• Creating strong partnerships across sales, marketing, and product teams• Focus on solving customer problems: making money, saving money, or saving time• Understanding the value of referrals and brand evangelism from satisfied customersFor more insights on customer success strategies, follow De'Edre Williams on LinkedIn and check out her Star Trek-themed newsletter that breaks down customer success concepts.Find De'Edra on Linkedin: https://www.linkedin.com/in/deedraswilliams/🌐 Website https://www.joedoestechtouch.com/📰 Subscribe to the JDTT Newsletter – Get raw insights, no-fluff frameworks, and tech touch tactics straight to your inbox: https://www.joedoestechtouch.com/jdttnewsletter 🎙️ Be a Guest on the Podcast Have a CS horror story or digital-first strategy worth sharing? Submit to be a guest:https://www.joedoestechtouch.com/podcast 🔗 Connect with Joe on LinkedIn https://www.linkedin.com/in/josephdigrande📺 Watch Full Episodes on YouTube: https://www.youtube.com/channel/UCaH58ojbaWym4ej_PedQ4Fw_______________________________Tools:Logitech Creators Blue Yeti USB Microphone: https://amzn.to/4nHOFDNLogitech Brio 4K Webcam: https://amzn.to/3GtKsmxSony WH-1000XM4 Noise Cancelling Wireless Headphones: https://amzn.to/44Q0xv4Apple 2024 MacBook Pro Laptop: https://amzn.to/4lH6u3W

May 26, 2025 • 32min
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 within customer organizations to protect against stakeholder turnover• Never confuse customer satisfaction with customer success – they aren't the same thingFollow Justin on LinkedIn: https://www.linkedin.com/in/justchappell/🌐 Website https://www.joedoestechtouch.com/📰 Subscribe to the JDTT Newsletter – Get raw insights, no-fluff frameworks, and tech touch tactics straight to your inbox: https://www.joedoestechtouch.com/jdttnewsletter 🎙️ Be a Guest on the Podcast Have a CS horror story or digital-first strategy worth sharing? Submit to be a guest:https://www.joedoestechtouch.com/podcast 🔗 Connect with Joe on LinkedIn https://www.linkedin.com/in/josephdigrande📺 Watch Full Episodes on YouTube: https://www.youtube.com/channel/UCaH58ojbaWym4ej_PedQ4Fw_______________________________Tools:Logitech Creators Blue Yeti USB Microphone: https://amzn.to/4nHOFDNLogitech Brio 4K Webcam: https://amzn.to/3GtKsmxSony WH-1000XM4 Noise Cancelling Wireless Headphones: https://amzn.to/44Q0xv4Apple 2024 MacBook Pro Laptop: https://amzn.to/4lH6u3W

May 20, 2025 • 42min
Default to Action: Why Your First Try Will Probably Fail - w/ Dillon Young
What 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 critical misunderstanding: sales operates in the realm of expectations while customer success deals with experiences. As Dillon explains, "In sales, it's all about expectations. You can sell a dream because customers have no basis for understanding what you can actually deliver." But when renewal time approaches, customers have accumulated a year of real experiences with your product, making empty promises worthless.This disconnect creates painful scenarios where CS teams are left managing disappointed clients who realize they're not getting what they were sold. Dillon shares a powerful story about confronting leadership over a top-performing salesperson who consistently sold "vaporware" - wasting implementation resources and guaranteeing eventual churn. Despite the obvious damage to the company's reputation and customer retention, leadership hesitated to address the issue because of short-term revenue targets driven by investor demands.The conversation explores practical strategies for success despite these challenges. Both hosts advocate for a "default to action" approach - starting with small, imperfect solutions rather than attempting to build comprehensive systems from scratch. As Dillon suggests, "If replacing a tool later would be relatively simple, don't spend more than 30 minutes deciding which one to implement." This philosophy prevents analysis paralysis and keeps teams moving forward through experimentation.Ready to transform your approach to customer success? Subscribe to Customer Unsuccess for more candid conversations about what doesn't work in CS—and how to turn those failures into your greatest opportunities for growth.🌐 Website https://www.joedoestechtouch.com/📰 Subscribe to the JDTT Newsletter – Get raw insights, no-fluff frameworks, and tech touch tactics straight to your inbox: https://www.joedoestechtouch.com/jdttnewsletter 🎙️ Be a Guest on the Podcast Have a CS horror story or digital-first strategy worth sharing? Submit to be a guest:https://www.joedoestechtouch.com/podcast 🔗 Connect with Joe on LinkedIn https://www.linkedin.com/in/josephdigrande📺 Watch Full Episodes on YouTube: https://www.youtube.com/channel/UCaH58ojbaWym4ej_PedQ4Fw_______________________________Tools:Logitech Creators Blue Yeti USB Microphone: https://amzn.to/4nHOFDNLogitech Brio 4K Webcam: https://amzn.to/3GtKsmxSony WH-1000XM4 Noise Cancelling Wireless Headphones: https://amzn.to/44Q0xv4Apple 2024 MacBook Pro Laptop: https://amzn.to/4lH6u3W

May 9, 2025 • 41sec
Customer [Un]Success - Teaser
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.🌐 Website https://www.joedoestechtouch.com/📰 Subscribe to the JDTT Newsletter – Get raw insights, no-fluff frameworks, and tech touch tactics straight to your inbox: https://www.joedoestechtouch.com/jdttnewsletter 🎙️ Be a Guest on the Podcast Have a CS horror story or digital-first strategy worth sharing? Submit to be a guest:https://www.joedoestechtouch.com/podcast 🔗 Connect with Joe on LinkedIn https://www.linkedin.com/in/josephdigrande📺 Watch Full Episodes on YouTube: https://www.youtube.com/channel/UCaH58ojbaWym4ej_PedQ4Fw_______________________________Tools:Logitech Creators Blue Yeti USB Microphone: https://amzn.to/4nHOFDNLogitech Brio 4K Webcam: https://amzn.to/3GtKsmxSony WH-1000XM4 Noise Cancelling Wireless Headphones: https://amzn.to/44Q0xv4Apple 2024 MacBook Pro Laptop: https://amzn.to/4lH6u3W


