The Customer UnSuccess Podcast

Madelyn DePrey, Global VP of Customer Success at Aircall, specializes in scalable customer success. She shares insights on moving 70% of SMBs to a pooled digital model and the importance of aligning sales with customer expectations. Madelyn discusses strategies like proactive journeys, in-app prompts, and lead scoring to enhance customer interactions. She emphasizes the need for collaboration between sales and product teams to drive retention and shares practical lessons on testing and iterating for success.

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 partner governance• choosing quality over quantity and pricing for value• handling escalations, lawsuits threats, and investor pressure• ethics under fire: refusing a $20,000 bribe• hypergrowth pitfalls: five CEOs in five years• asking sharper questions before taking a role• proactive learning and problem-led improvementIf you got some value from this conversation, hit subscribe, leave a rating or review, share it with someone who's also out there trying to build a better customer success or go-to-market strategy, even if it's messy along the way.And if you want more frameworks, tools, automated playbooks, check out JodasX.com and subscribe to our newsletter.🎙️ Guest: Jerry Van Vort 📣 Find Jerry: LinkedIn: https://www.linkedin.com/in/jerryjv/ 🔥 Topics Covered: 🟣 Lessons from transitioning careers: from winemaking 🍷 to cannabis 🌱 to SaaS 🟣 Why quality over quantity matters in customer delivery 🟣 How ethics under pressure (like refusing a $20k bribe) builds long-term trust 🟣 The chaos of hyper-growth: scaling from 12 → 150 employees in 12 months 🟣 Surviving 5 CEOs in 5 years and what that taught about leadership resilience 🟣 Why interviewing a company is just as important as them interviewing you 🟣 The three questions Jerry always asks before joining a new company 🟣 The importance of structure: KPIs, compensation fairness, and bringing in outside talent🌐 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/4nHOFDN Logitech Brio 4K Webcam: https://amzn.to/3GtKsmx Sony WH-1000XM4 Noise Cancelling Wireless Headphones: https://amzn.to/44Q0xv4 Apple 2024 MacBook Pro Laptop: https://amzn.to/4lH6u3W

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.com/ Substack: https://knowandflourish.substack.com/ 🔥 Topics Covered: 🟣 Why career strategy matters just as much as customer strategy 🟣 The underestimated leadership skills every CSM should be developing 🟣 How to align personal growth with company growth without burning out 🟣 The importance of intentionality in career moves and leadership development 🟣 Why influencing up is critical for CSMs who want to lead with impact 🟣 The role of vulnerability and connection in effective leadership (inspired by Brené Brown)📚 Resources & Mentions:The Five Dysfunctions of a Team – Patrick Lencioni - https://amzn.to/3VICoSTThe Myth of the Nice Girl – Fran Hauser - https://amzn.to/4gM8bfaRadical Candor – Kim Scott - https://amzn.to/46ESMsA 🌐 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/4nHOFDN Logitech Brio 4K Webcam: https://amzn.to/3GtKsmx Sony WH-1000XM4 Noise Cancelling Wireless Headphones: https://amzn.to/44Q0xv4 Apple 2024 MacBook Pro Laptop: https://amzn.to/4lH6u3W

In this engaging discussion, Christy Faltorusso, a seasoned customer success leader and Chief Customer Officer, reveals the lurking dangers of competitive churn. She illustrates how Customer Success teams often lack the awareness to protect their accounts, highlighting a flagship client that silently migrated to a competitor. Christy stresses the importance of monitoring customer language and subtle cues, and warns against the pitfalls of slashing prices. With strategic insights on defensive playbooks, she empowers listeners to stay vigilant against sneaky rival tactics.

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 model to ensure both parties have "skin in the game"• Unlike LinkedIn, Success Panda allows professionals to monetize their knowledge through a marketplace for templates and resources• Anonymous posting features enable professionals to ask sensitive questions without fear• Brad's "professionally brush your teeth" analogy highlights the importance of regular career maintenance• Events, communities, and resource aggregation help provide a one-stop shop for CS professionals• Mentorship dramatically impacts career trajectory, with 69% of CEOs crediting mentors with helping them make better decisions• The book "Thinking in Moments" teaches how to engineer peak experiences in customer journeysJoin Success Panda's community for customer success professionals at successpanda.com, or connect with Brad on LinkedIn.🎙️ Guest: Brad Davis 📣 Find Brad: LinkedIn: https://www.linkedin.com/in/contactbraddavis/📌 In This Episode: Brad Davis joins Joe Di Grande on Customer [Un]Success to share his journey from building farmhouse tables in his Cincinnati garage to founding Success Panda, a platform designed to help Customer Success professionals connect, learn, and grow. From the lessons of running a six-figure side hustle to the vision for a CS marketplace, Brad highlights the scrappy side of entrepreneurship and the systems that turn ideas into impact.📚 Resources & Mentions: Success Panda – Customer Success networking & marketplace: https://successpanda.io/ 🌐 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/4nHOFDN Logitech Brio 4K Webcam: https://amzn.to/3GtKsmx Sony WH-1000XM4 Noise Cancelling Wireless Headphones: https://amzn.to/44Q0xv4 Apple 2024 MacBook Pro Laptop: https://amzn.to/4lH6u3W

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 as long as those who don't, challenging conventional wisdom• Early warning signs of churn can be detected in the first customer interaction, often before any obvious signals of trouble• "Customer bonding" occurs when clients see your company as integral to their success and a source of valuable expertise• CSMs should use "power statements" to confidently assert expertise rather than making tentative suggestions• Health scores typically predict churn too late to take effective action—intervention must happen much earlier• The most effective customer success approach focuses on driving measurable business results rather than satisfactionFor free resources including research data, e-books, and a course on churn, visit gregdaines.com or connect with Greg on LinkedIn: https://www.linkedin.com/in/gregdaines/Behind the Cloud: The Untold Story of How Salesforce.com Went from Idea to Billion-Dollar Company-and Revolutionized an Industry: https://amzn.to/47JWDXz🌐 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/4nHOFDN Logitech Brio 4K Webcam: https://amzn.to/3GtKsmx Sony WH-1000XM4 Noise Cancelling Wireless Headphones: https://amzn.to/44Q0xv4 Apple 2024 MacBook Pro Laptop: https://amzn.to/4lH6u3W

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-Salesforce integration to measure engagement• Learned that having two CSMs per session provides better knowledge coverage• Discovered that customers in EMEA preferred afternoon sessions despite earlier options• Recommendation: run sessions at least weekly and keep them open to all customers• Key insight: sometimes less structure creates more value for customersFind Kat Brigham on LinkedIn to learn more about digital customer success strategies and scaled education approaches.🌐 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/4nHOFDN Logitech Brio 4K Webcam: https://amzn.to/3GtKsmx Sony WH-1000XM4 Noise Cancelling Wireless Headphones: https://amzn.to/44Q0xv4 Apple 2024 MacBook Pro Laptop: https://amzn.to/4lH6u3W

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• Dealing with leadership transitions left Tiffany without proper mentorship or support• The importance of "matching energy in the room" by bringing leadership to executive meetings• How industry knowledge builds the confidence needed to handle executive pushback• Managing different personality types is a crucial but often untaught skill in customer success• The pros and cons of working with different customer segments (small/agile vs. enterprise/complex)• Mental health considerations are essential for CSMs who serve as the "face" of the company• Valuable resources for CSMs include LinkedIn experts like Carly Agar and Marcus Rentsch🎙️ Guest: Tiffany Parkes Senior Customer Success Manager | User Interviews📣 Find Tiffany: LinkedIn: https://www.linkedin.com/in/tiffany-parkes-024a0443/ 🔥 Topics Covered: 🟣 Moving from mid-market to strategic accounts and handling imposter syndrome 🟣 Why “matching the energy in the room” matters when presenting to executives 🟣 Navigating C-level personalities and using emotional intelligence as a CSM 🟣 Building confidence without deep industry knowledge (and how to “borrow” it) 🟣 The power of influence when your champions aren’t decision makers 🟣 Leaning into mental health as a core skill for CSMs 🟣 How to handle rejection and pushback without losing credibility💡 Shoutouts & Mentions:Carly Agar — Interview prep & CSM career coaching - https://www.linkedin.com/in/carly-agar/ Marcus Rentsch — Value-focused Customer Success insights- https://www.linkedin.com/in/markus-rentsch-customer-value-led-growth-for-saas/ Mel Robbins — Podcast & content on mindset and communication — https://open.spotify.com/show/7vz4RYsD5MulTCrcH478t1?si=24c6426f48414838 🌐 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/4nHOFDN Logitech Brio 4K Webcam: https://amzn.to/3GtKsmx Sony WH-1000XM4 Noise Cancelling Wireless Headphones: https://amzn.to/44Q0xv4 Apple 2024 MacBook Pro Laptop: https://amzn.to/4lH6u3W

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 backfire, resulting in disengaged customers and last-minute scrambling• The "Rule of Seven" marketing concept applies to customer success—customers need approximately seven touchpoints before taking action• Clean data is essential before implementing any automation to avoid embarrassing misfires• Internal automation carries less risk than customer-facing automation and can provide quick wins• Content-based resources like self-service guides and value realization frameworks provide immediate value with lower technical complexity• Cross-functional executive alignment is crucial for effective risk mitigation• Start building touchpoints throughout the entire customer journey instead of leaving gaps between onboarding and renewalJoin DCS Connect, Marie's Slack community for Digital CS professionals, to connect with others building scaled customer success programs. Learn more by connecting with Marie on LinkedIn.🎙️ Guest: Marie Lunney Founder | DCS Connect | Director of Scaled Customer Experience at Bynder📣 Find Marie: LinkedIn: https://www.linkedin.com/in/marielunney1 🔥 Topics Covered: 🟣 Why focusing your first digital CS motion on renewals can backfire 🟣 The benefits of starting with onboarding & early adoption initiatives 🟣 How executive alignment strengthens risk mitigation efforts 🟣 Why clean, consistent data must come before automation 🟣 Internal automation as a low-risk, high-reward starting point 🟣 Leveraging content and self-serve resources for scalable impact 🟣 Balancing tech and human touch in scaled customer journeys 🟣 Common pitfalls to avoid when launching your first scaled program💡 Shoutouts & Mentions:DCS Connect — Community for Digital Customer Success professionals — https://airtable.com/appLGhZyujOoYp8BQ/shr4ixoZmB8hBoLbM Pavilion — Global GTM & CS community — https://www.joinpavilion.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/4nHOFDN Logitech Brio 4K Webcam: https://amzn.to/3GtKsmx Sony WH-1000XM4 Noise Cancelling Wireless Headphones: https://amzn.to/44Q0xv4 Apple 2024 MacBook Pro Laptop: https://amzn.to/4lH6u3W

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• Shifting from "No" to "Yes, but" to "Yes, and" approaches transformed team dynamics• The customer journey must be owned by the company, not individual departments• Creating data-driven triggers helps align teams around customer advocacy opportunities• AI is revolutionizing how CS teams identify patterns and predict customer behaviors • Revenue is a "full-contact team sport" requiring all departments to work together• Executive coaching provides valuable perspective for leadership developmentIf you're in customer success, sales or other go-to-market motions, stick around to hear from the best. For more frameworks, tools, and automated playbooks, check out jodastech.com and subscribe to our newsletter.🎙️ Guest: Anthony DeShazor Chief Customer Officer | GTM & RevOps Architect | Former “VP of No”📣 Find Anthony: LinkedIn: https://www.linkedin.com/in/adeshazor/ 📌 In This Episode: Anthony joins Joe Di Grande on Customer [Un]Success to unpack the lessons behind earning — and evolving beyond — the title of “VP of No.” He shares how customer success leaders can go from gatekeeping to growth-enabling.🔥 Topics Covered: 🟣 The real story behind “VP of No” and “Helicopter CCO” 🟣 How to shift from “No” → “Yes, but” → “Yes, and” 🟣 Why too many internal teams talking to the customer = chaos 🟣 Lessons on cross-functional alignment between CS, Sales & Marketing 🟣 The role of AI in building advocacy workflows 🟣 What happens when CS owns more of the GTM strategy 🟣 Self-awareness and humility in executive leadership 🟣 The importance of psychological safety on your team💡 Shoutouts & Mentions:Pavilion — a go-to CS/RevOps community, Anthony is active in- https://www.joinpavilion.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/4nHOFDN Logitech Brio 4K Webcam: https://amzn.to/3GtKsmx Sony WH-1000XM4 Noise Cancelling Wireless Headphones: https://amzn.to/44Q0xv4 Apple 2024 MacBook Pro Laptop: https://amzn.to/4lH6u3W