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.

  1. Apr 6

    How To Win Over The C‑Suite and Turn Champions Into Heroes w/ Rachel Provan CEO of Provan Success

    We explore how to build customer success from scratch and make it visible to executives by speaking in outcomes, not activities. We lean on psychology to drive adoption, create champions, and pre‑pave ethical expansions while AI takes the busywork. • CS built in stages with outcome targets appropriate to company maturity • Why executives don’t “get” CS and how to lead with numbers and loss avoidance • Hyperbolic discounting and presenting near‑term impact to secure support • Onboarding that triggers dopamine via tiny steps and quick wins • Make champions the hero by tying work to promotions and visible wins • From usage to impact: show revenue protection, productivity gains, and margin • Pre‑paving expansions at 75 percent progress to honor momentum • Focus on the job that matters, not every feature in the product • Practical scripts, story banks, and aligning with ICP to ease sales and CS handoffs • Recommended reads: Kahneman, Gladwell, Cialdini, Voss; Rachel’s site resources If you got some value from this conversation, hit subscribe, leave a rating or review, and 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 Check out JoeDoesTechTouch.com and subscribe to our newsletter. That link is in the description  🎙️ Guest: Rachel Provan Founder & CEO, Provan Success 📣 Find Rachel: Website: provansuccess.com Podcast: Psychology of Customer Success LinkedIn: https://www.linkedin.com/in/rachelhprovan/  🔥 Topics Covered: 🟣 Building a CS department from scratch — lessons learned as a player-coach and scrappy early-stage leader 🟣 Communicating with the C-suite — “Be brief, be right, bring charts, be gone” 🟣 Understanding executive psychology — why focusing on “what’s in it for me?” drives better outcomes 🟣 Using loss aversion to influence decision-making and drive customer adoption 🟣 Onboarding with dopamine — tiny wins and positive reinforcement for habit-building 🟣 Making the customer the hero — focusing on outcomes, not features 🟣 Practical strategies for demonstrating business impact in measurable terms (ROI, productivity, retention) 🟣 Balancing automation and AI with human connection — why non-human tasks free up CS to deliver real value 🟣 Continuous learning for CS leaders — resources, books, and frameworks to level up 🌐 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

    How To Win Over The C‑Suite and Turn Champions Into Heroes w/ Rachel Provan CEO of Provan Success

  2. Mar 23

    Stop People-Pleasing, Start Outcome-Pleasing w/ Jess Szivos VP of Customer Success at Invisory

    We unpack why generic 30-60-90 plans fall flat and how to turn them into customer coauthored blueprints tied to KPIs. Jess shares therapist-grade discovery tactics, persona-aware messaging, and how data plus boundaries create real influence and sustainable results. • shifting from templated onboarding to coauthored success plans • using layered why questions and silence to deepen discovery • mapping who’s who in the zoo to build champions • pacing value with milestones instead of month-one heroics • tailoring talk tracks for operators vs executives • combining quantitative metrics with voice of the customer • strengthening cross-functional ties and shared ownership • setting boundaries to avoid reactive, always-on expectations • growing career confidence with mentors, habits, and a tangible toolkit • practical resources and small weekly routines that compound If you got some value from this conversation, hit subscribe, leave a rating or review, and 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 JoeDoesTechTouch.com and subscribe to our newsletter 🎙️ Guest: Jess Szivos Vice President of Customer Success at Invisory 📣 Find Jess: LinkedIn: https://www.linkedin.com/in/jlszivos/  🔥 Topics Covered: 🟣 How to create a personalized 30-60-90 day plan as a blueprint for customer success 🟣 Why active listening and giving space in conversations builds trust and customer rapport 🟣 Strategies for aligning customer goals with your own metrics and success plans 🟣 “Who’s Who in the Zoo” approach to mapping key stakeholders and building champions 🟣 Managing expectations, pacing, and slowing down to focus on long-term impact 🟣 How to leverage qualitative and quantitative data to inform decisions and demonstrate value 🟣 Best practices for cross-functional collaboration with product, marketing, and other internal teams 🟣 The importance of protecting your boundaries while maintaining a growth mindset 🟣 Using your voice in the organization to influence and advocate for customers 🟣 Investing in yourself: continuous learning, mentorship, and building your personal toolkit 🌐 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

    Stop People-Pleasing, Start Outcome-Pleasing w/ Jess Szivos VP of Customer Success at Invisory

  3. Mar 9

    Chaos Threshold: Startup CS Vs Enterprise w/ Maranda Dziekonski Chief Customer Officer at Fexa

    We compare enterprise customer success with early-stage startup CS and get honest about chaos tolerance, ambiguity, politics, and fit. Maranda shares hiring exercises, interview tactics, and career moves that protect your story and mental health. • defining your threshold for chaos and ambiguity • differences between regulated enterprise and scrappy startup CS • interview questions that reveal real process and ownership • anti‑goals as a filter for roles and culture • hiring exercises that surface prioritization and advocacy • handling ambiguity without freezing or overthinking • enterprise navigation skills and matrixed influence • research tactics, backchannels, and panel design • being open to a title step back with clear growth paths • resources for learning and the value of discerning advice If 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 JoedoesTechTouch.com and subscribe to our newsletter. That link is in the description. 🎙️ Guest: Maranda Dziekonski Chief Customer Officer at Fexa 📣 Find Maranda: LinkedIn: https://www.linkedin.com/in/marandaanndziekonski/  🔥 Topics Covered: 🟣 How to assess your tolerance for ambiguity and chaos before joining a new company 🟣 Lessons learned transitioning from highly structured enterprises to fast-moving startups 🟣 Why defining your “anti-goals” can help guide smarter career decisions 🟣 How CS professionals can prepare for interviews and advocate for themselves effectively 🟣 The difference in evaluating roles at startups, growth-stage, and large organizations 🟣 How organizational structure, SOPs, and culture impact CS success 🟣 Key strategies for navigating large or matrixed organizations as a customer-facing professional 🟣 Advice on being open to lateral moves for long-term career growth 🟣 Insights on identifying the right environment to protect your mental health and performance 🟣 How to leverage prior experiences to succeed in diverse CS settings 🌐 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

    Chaos Threshold: Startup CS Vs Enterprise w/ Maranda Dziekonski Chief Customer Officer at Fexa

  4. Feb 23

    From Surprise Non-Renewal To Sales-CS Alignment w/ Guy Galon Chief CS & Revenue Leader at Obrela

    We unpack a “sure thing” renewal that fell apart, the hidden decision makers who swung the outcome, and why quiet QBRs signal danger. We also break down a high-stakes implementation sold ahead of product readiness and how disciplined alignment turned risk into long-term trust. • mapping influence beyond the budget owner • spotting engagement drop-offs as churn signals • asking hard questions in QBRs to test intent • coordinating sales and CS on renewals and expansions • managing design-partner projects without overpromising • qualifying ICP to control cost to serve • running post-mortems that change behavior • building a learning mindset across teams • book recommendations for CS leaders If you got some value from this conversation, hit subscribe, leave a rating and review, and 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 JoeDoesTechTouch.com and subscribe to our newsletter 🎙️ Guest: Guy Galon Chief Customer Success & Revenue Leader at Obrela 📣 Connect with Guy: LinkedIn: https://www.linkedin.com/in/guy-galon-b1a80/  Website & newsletter: https://www.thecscycle.com/  🔥 Topics Covered: 🟣 Lessons from a missed renewal: reading signals, engaging all decision-makers, and learning from churn 🟣 Selling to the wrong customer: how early alignment on ICP and expectations saves resources 🟣 Collaborating with sales, product, and other teams to deliver long-term customer value 🟣 Importance of post-mortems to identify gaps and improve processes 🟣 Continuous learning: soft skills, asking the right questions, and reflection 📚 Resources Mentioned: 🟣 Atomic Habits  — https://www.amazon.com/Atomic-Habits-Proven-Build-Break/  🟣Built to Last - https://www.amazon.com/Built-Last-Successful-Visionary-Essentials/  🟣The Startup of You - https://www.amazon.com/Start-up-You-Future-Yourself-Transform/  🟣Surrounded by Idiots - https://www.amazon.com/Surrounded-Idiots-Revised-Expanded-Effectively/  🌐 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

    From Surprise Non-Renewal To Sales-CS Alignment w/ Guy Galon Chief CS & Revenue Leader at Obrela

  5. Feb 9

    The True Cost Of A Bad-Fit Customer And How To Walk Away w/ Shari Srebnick

    We trace a marquee deal that imploded at handoff, then rebuild the path from close to value with practical fixes for alignment, multithreading, and fit. Along the way, we count the real cost to serve and explain why some logos deserve a respectful no. • sales and CS alignment around goals, metrics, and roles • lean handoffs with internal kickoff and joint success plans • multithreading the retention group beyond the buyer • measuring cost to serve against ARR and CAC recovery • recognizing bad-fit customers and when to walk away • replacing heroics with repeatable processes and enablement • integrated tools and shared insights across CRM and CSP • learning paths and resources for strategic CSM growth If you got some value from this conversation, hit subscribe, leave a rating or review, and 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. Check out JoeDoesTechTouch.com and subscribe to our newsletter. 🎙️ Guest: Shari Srebnick Customer Success leader with 10+ years of experience 📣 Find Shari: LinkedIn: https://www.linkedin.com/in/sharisrebnick/  🔥 Topics Covered: 🟣 A chaotic “drop-the-mic” deal and what it teaches about sales–CS alignment 🟣 Why single-threaded deals and poor handoffs hurt time-to-value and churn risk 🟣 How to escalate issues without finger-pointing 🟣 Redesigning handoffs and internal kickoffs for stronger account plans 🟣 When heroics hide deeper ICP or strategy problems 🟣 Multi-threading post-sale and engaging the right contacts 🟣 Understanding cost to serve, CAC, and profitable vs. unprofitable accounts 🟣 Shared enablement between Sales and CS 📚 Resources Mentioned: 🟣 The Strategic Customer Success Manager — Lindsey’s top recommendation and team-wide read - https://www.amazon.com/Strategic-Customer-Success-Manager-Blueprint/ 🟣Multipliers - https://www.amazon.com/s?k=Multipliers&crid=XALJ7SZ10BK1&sprefix=multiplier%2Caps%2C175&ref=nb_sb_noss_1  🟣Impact Players: How to Take the Lead, Play Bigger, and Multiply Your Impact - https://www.amazon.com/Impact-Players-Take-Bigger-Multiply/  🟣Lean Analytics: Use Data to Build a Better Startup Faster - 🌐 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

    The True Cost Of A Bad-Fit Customer And How To Walk Away w/ Shari Srebnick

  6. Jan 26

    Saying Yes Too Much Hurts Results w/ Lindsey LeFaivre VP of Customer Success at AchieveIt

    We unpack how saying yes too fast derails outcomes and how visible boundaries make better teams. Lindsey LeFaivre shares hard-won lessons from a 1,500-branching workflow misfire to a delivery-room out-of-office, turning mistakes into practical leadership habits. • discovery before commitment on complex requests • validation of true customer needs and success metrics • small-team pressure, imposter syndrome, overwork triggers • rituals for boundaries and recovery during remote work • non negotiables on the calendar and offline windows • resource requests as a leadership signal not a weakness • meeting hygiene, playbooks and focus-time protection • interviewing for culture and real work-life balance • community learning and strategic customer success mindset If you got some value from this conversation, hit subscribe, leave a rating or review, and 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. For more frameworks, tools, automated playbooks, check out JoeDoesTechTouch.com and subscribe to our newsletter. 🎙️ Guest: Lindsey LeFaivre Vice President of Customer Success at AchieveIt 📣 Find Lindsey: LinkedIn: https://www.linkedin.com/in/lindseyingalls/  🔥 Topics Covered: 🟣 Why early-career CS professionals struggle to say “no” — and how that leads to burnout 🟣 A real startup story of working 24 straight hours on a customer request that never shipped 🟣 How imposter syndrome drives unhealthy work habits in Customer Success 🟣 The hidden cost of always saying “yes” to customers instead of asking better questions 🟣 Why work-life balance isn’t 50/50 — it comes in seasons and tradeoffs 🟣 Lessons learned from working through maternity leave during COVID 🟣 Why asking for help is a leadership skill — not a weakness 🟣 The importance of setting and communicating non-negotiables (like school pickup time) 🟣 How leaders must model healthy boundaries to give teams permission to do the same 🟣 Why results matter more than hours logged — especially in remote CS teams 🟣 How to evaluate company culture by asking leaders what their work-life balance looks like 🟣 Why Customer Success culture thrives on generosity, transparency, and shared learning 📚 Resources Mentioned: 🟣 The Strategic Customer Success Manager — Lindsey’s top recommendation and team-wide read - https://www.amazon.com/Strategic-Customer-Success-Manager-Blueprint/ 🟣 Atlanta Customer Success Community — https://www.atlcs.community/ 🌐 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

    Saying Yes Too Much Hurts Results w/ Lindsey LeFaivre VP of Customer Success at AchieveIt

  7. Jan 12

    How We Turn Angry Clients Into Loyal Advocates w/ Rob Zambito CEO of Success Scaled Consulting

    We trade war stories from diner counters and real estate closings to show how psychology, better playbooks, and value-add concessions defuse escalations and protect renewals. Rob shares Feel–Felt–Found, digital cancellation flows, and why discounts can backfire. • reframing escalations as signals of product importance • teaching teams Feel–Felt–Found to de-escalate • avoiding discount reflex in renewals • using value-add concessions before price cuts • building digital cancellation flows that retain • applying defaults, loss aversion and social proof • separating usage, adoption, ROI and value • behavior design lessons from Planet Fitness • books, tools and journaling for learning loops • how to contact Rob for frameworks and support If you got some value from this conversation, hit subscribe, leave a rating or review, and 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 besty along the way. For more frameworks, tools, automated playbooks, check out Johda'sTechTouch.com and subscribe to our newsletter. That link is in the description. 🎙️ Guest: Rob Zambito Founder & CEO of Success Scaled Consulting 📣 Find Rob: LinkedIn: https://www.linkedin.com/in/rob-zambito/  🔥 Topics Covered: 🟣 Why customer escalations increase as products become more mission-critical 🟣 Reframing escalations as signals of value — not Customer Success failure 🟣 The danger of positioning CS as the default “escalation department” 🟣 How poor escalation handling unintentionally trains customers to escalate again 🟣 Why discounts are the laziest (and most harmful) concession during escalations 🟣 Using psychology — loss aversion, reciprocity, and defaults — to guide better outcomes 🟣 How the Feel–Felt–Found framework works when used for emotional validation (not deflection) 🟣 The role of executive presence and confidence in high-stakes customer conversations 🟣 Why customers don’t want explanations — they want to feel heard first 🟣 How CS leaders can design escalation paths that protect long-term value, not just short-term peace 🌐 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

    How We Turn Angry Clients Into Loyal Advocates w/ Rob Zambito CEO of Success Scaled Consulting

  8. 10/20/2025

    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 • proactive journeys with in-app prompts and time-based triggers • lead scoring and enrichment to flag high-potential accounts • applying sales science to expansion and retention • limits of health scores and importance of multi-threading • partnering with product on onboarding as a retention lever • cross-functional KPIs around NRR, GRR, and first six-month retention • piloting changes in APAC before global rollout • iterate quickly without waiting for perfect data If you got some value from this conversation, hit subscribe, leave a rating or review, and 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 Johto'sTechTouch.com and subscribe to our newsletter. 🎙️ Guest: Madelyn DePrey  Global VP of Customer Success at Aircall 📣 Find Madelyn:  LinkedIn: https://www.linkedin.com/in/madelyn-deprey-29a91642/  🔥 Topics Covered:  🟣 How Aircall transformed 70% of its customer base into a digital-first success model  🟣 Why digital CS starts at the top of the funnel — not post-sale  🟣 The risks of moving too fast in a scaled CS rollout (and how to recover)  🟣 How to apply the science of sales — lead scoring, enrichment & segmentation — to post-sale success  🟣 Why “perfect data” doesn’t exist and how to execute while still learning  🟣 Lessons from aligning Product, Sales, and CS around shared KPIs and OKRs  🟣 How the APAC region became Aircall’s testing ground for digital CS innovation  🟣 The power of cross-functional empathy and managing up when goals don’t align  🟣 Why hospitality belongs in tech — inspired by Danny Meyer’s Setting the Table  🟣 Madelyn’s favorite leadership resource: Kleiner Perkins’ “Grit” 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/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

    Digital CS, Done The Hard Way w/ Madelyn DePrey Global VP of Customer Success @ Aircall
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Ratings & Reviews

5
out of 5
4 Ratings

About

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.

Information

  • Creator
    Joe Di Grande
  • Years Active
    2025 - 2026
  • Episodes
    29
  • Rating
    Explicit
  • Copyright
    © 2026 The Customer UnSuccess Podcast
  • Show Website
    The Customer UnSuccess Podcast