The Customer UnSuccess Podcast

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 compoundIf 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 SzivosVice 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/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

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 adviceIf 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 DziekonskiChief 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/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

Guy Galon, Chief Customer Officer at Obrela and author of the CS Cycle newsletter, shares tales of a surprise non-renewal and the hidden influencers who changed the outcome. He explores quiet QBRs as danger signs, selling implementations before product readiness, and how tight sales-CS alignment and post-mortems turn mistakes into learning. Practical frameworks and book recs sprinkled throughout.

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 growthIf 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 SrebnickCustomer 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/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

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 mindsetIf 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 LeFaivreVice 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/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

Rob Zambito, Founder and CEO of Success Scaled Consulting, shares vital insights on turning customer escalations into opportunities. He explains the Feel–Felt–Found method for de-escalation, emphasizing that escalations often signal a product's importance rather than failure. Zambito advocates for value-add concessions over discounts and discusses retention strategies like digital cancellation flows. He also delves into consumer psychology, highlighting effects of loss aversion and reciprocity, and shares personal anecdotes that illustrate building better customer relationships.

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/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

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/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

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.