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 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 everyth

The Customer UnSuccess Podcast is a business podcast hosted by Joe Di Grande, with 29 episodes on record and a Required Pod Score of 80.

Joe Di Grande hosts The Customer UnSuccess Podcast, a business show with 29 episodes published.

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  The Customer UnSuccess Podcast

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

  Apr 6, 202650 minS0

  <p>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.<br/><br/>• CS built in stages with outcome targets appropriate to company maturity<br/>• Why executives don’t “get” CS and how to lead with numbers and loss avoidance<br/>• Hyperbolic discounting and presenting near‑term impact to secure support<br/>• Onboarding that triggers dopamine via tiny steps and quick wins<br/>• Make champions the hero by tying work to promotions and vi...

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  The Customer UnSuccess Podcast

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

  Mar 23, 202648 minS0

  <p>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.<br/><br/>• shifting from templated onboarding to coauthored success plans<br/>• using layered why questions and silence to deepen discovery<br/>• mapping who’s who in the zoo to build champions<br/>• pacing value with milestones instead of month-one heroics<br/>• tailoring talk tracks for operators vs executives<br/>• combining quantitative metrics with voice of the customer<br/>• strengthening cross-functional ties and shared...

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  The Customer UnSuccess Podcast

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

  Mar 9, 202641 minS0

  <p>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.<br/><br/>• defining your threshold for chaos and ambiguity<br/>• differences between regulated enterprise and scrappy startup CS<br/>• interview questions that reveal real process and ownership<br/>• anti‑goals as a filter for roles and culture<br/>• hiring exercises that surface prioritization and advocacy<br/>• handling ambiguity without freezing or overthinking<br/>• enterprise navigation skills and matrixed influence<br/>• research tactics, backchannels, and panel design<br/>•...

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  The Customer UnSuccess Podcast

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

  Feb 23, 202635 minS0

  <p>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.<br/><br/>• mapping influence beyond the budget owner<br/>• spotting engagement drop-offs as churn signals<br/>• asking hard questions in QBRs to test intent<br/>• coordinating sales and CS on renewals and expansions<br/>• managing design-partner projects without overpromising<br/>• qualifying ICP to control cost to serve<br/>• running post-mortems that change behavior<br/>• building a learning mindset a...

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  The Customer UnSuccess Podcast

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

  Feb 9, 202650 minS0

  <p>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.<br/><br/>• sales and CS alignment around goals, metrics, and roles<br/>• lean handoffs with internal kickoff and joint success plans<br/>• multithreading the retention group beyond the buyer<br/>• measuring cost to serve against ARR and CAC recovery<br/>• recognizing bad-fit customers and when to walk away<br/>• replacing heroics with repeatable processes and enablement<b...

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