Customer Success Therapy

Alexandra Sagaydak
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  • Updated twice weekly

🎙 Customer Success Therapy — with Alexandra Sagaydak. The CS podcast that isn't about frameworks, metrics, or revenue plays. I'm Alexandra Sagaydak. After 10 years operating in CS, I got tired of conferences where everyone says the same five things and nobody says what they actually think. So I built this. Every episode, I sit down with a CS, SaaS, or GTM operator and we get into the stuff they don't put on LinkedIn — the decisions they second-guess, the moments they almost quit, the takes they only share after a glass of wine. The guest is the star. The conversations are honest. The therapy is mutual. We listen and we don't judge.

  1. 4 days ago

    Dannah Vaughan: Why CS Leaders Build Their Own Little Kingdoms

    Customer Success is changing fast — and Dannah Vaughan believes CS leaders need to think far beyond traditional metrics. In this episode, we talk about why hiring great CSMs has become harder, how AI can create blind spots in recruiting, and why Customer Success is still difficult to define even inside leadership teams. Dannah also explains why CS leaders need to understand metrics like cost to serve, CAC, CLTV, and renewal forecasting — not just NRR and GRR — and why executive teams can sometimes turn into their own little “kingdoms” when pressure and fear start shaping decisions. We also get into the personal side of leadership: what layoffs taught Dannah about confidence and identity, whether building a personal brand actually helps you get hired, and why AI still needs a human in the loop. Dannah Vaughan is a Customer Success executive, AI-powered leader, and founder of Rebels of SaaS. 🔗 Connect with Dannah Vaughan: https://www.linkedin.com/in/dannahvaughan/ — Customer Success Therapy is hosted by Alexandra Sagaydak. 🔗 Follow Alexandra on LinkedIn: https://www.linkedin.com/in/alexandrasagaydak/ Join the AI CS Hub: https://aicshub.com/ 1:1 coaching for CSMs and CS leaders + consulting for B2B SaaS: https://calendly.com/ai-cs-hub/coaching-session

  2. 31 Aug

    The Harsh Truth About Finding a CS Job in 2026 | Noah Little

    The CS job search is broken — and Noah Little has spent years figuring out how to help CSMs navigate it. After years working in Customer Success, Noah started helping friends land their next roles. That eventually turned into a business focused specifically on helping CSMs get hired. In this episode, we talk about the harsh reality of the CS job market, why rejection can derail CSMs, why applying consistently matters more than endlessly preparing, and why being a great CSM doesn't automatically mean you'll get hired. Noah also challenges the idea that you need the “right” industry background, explains why hiring processes have become so long, and shares what separates candidates who keep getting rejected from those who eventually get the offer. Plus, we get into the part nobody likes talking about: how much work a serious job search actually requires. Noah Little is an Enterprise Customer Success Manager and career coach helping CSMs navigate the modern job market. 🔗 Connect with Noah Little: https://www.linkedin.com/in/noah-little — Customer Success Therapy is hosted by Alexandra Sagaydak. 🔗 Follow Alexandra on LinkedIn: https://www.linkedin.com/in/alexandrasagaydak/ Join the AI CS Hub: https://aicshub.com/ 1:1 coaching for CSMs and CS leaders + consulting for B2B SaaS: https://calendly.com/ai-cs-hub/coaching-session

  3. 16 Aug

    Andrea Bumstead: The Biggest Career Mistake Customer Success Leaders Make

    Andrea Bumstead's LinkedIn makes her career look perfectly linear. It wasn't. When Andrea moved from Director to VP of Customer Success, people told her she wasn't ready. She was told to become a Senior Director first. Instead, she invested in executive coaching, took responsibility for her own development, and made the transition anyway. In this episode, we talk about why CS leaders wait too long to make their next move, why executives tune out traditional QBRs, and how Andrea's 15-Minute QBR gets leadership attention. We also talk about revenue, executive credibility, and the 70% rule she uses to make big career decisions. Andrea Bumstead is the Founder & CEO of CS Impact, a two-time VP of Customer Success, and creator of the 15-Minute QBR. 🔗 Connect with Andrea on LinkedIn: https://www.linkedin.com/in/andreabumstead — Customer Success Therapy is hosted by Alexandra Sagaydak. 🔗 Follow Alexandra on LinkedIn: https://www.linkedin.com/in/alexandrasagaydak/ Join the AI CS Hub: https://aicshub.com/ 1:1 coaching for CSMs and CS leaders + consulting for B2B SaaS: https://calendly.com/ai-cs-hub/coaching-session

  4. 3 Aug

    Jeff Kushmerek: Is LinkedIn Making Customer Success Worse?

    Jeff Kushmerek quit posting on LinkedIn for two years. He's back on this episode to explain why — and it's not a compliment to the industry. After 25 years running post-sale at companies like Brightcove, Virgin Pulse, and Thought Industries, Jeff founded Infinite Renewals, where he's helped retain $1.8B in ARR. He's also the author of two books on post-sales operations. We talk about why he calls certain CSMs "huggers" who avoid revenue conversations, why onboarding is the wedding and not the honeymoon, the 4 R's framework he built from working with hundreds of CS teams, how he can spot a bad CS leader in under five minutes, and why he thinks the loudest voices in Customer Success online rarely did the actual job. Plus: the car accident that made him rethink how he runs his business, and his blunt advice for anyone too burned out to fix their own team. Jeff is the Founder and CEO of Infinite Renewals. 🔗 Connect with Jeff on LinkedIn: https://www.linkedin.com/in/jeffkushmerek 🔗 Infinite Renewals: https://infiniterenewals.com/ — Customer Success Therapy is hosted by Alexandra Sagaydak. 🔗 Follow Alexandra on LinkedIn: https://www.linkedin.com/in/alexandrasagaydak/ Join the AI CS Hub: https://aicshub.com/ 1:1 coaching for CSMs and CS leaders + consulting for B2B SaaS: https://calendly.com/ai-cs-hub/coaching-session

  5. 29 Jul

    Erica Phelps: Manage the Game, Not Just the Customer

    Erica Phelps spent nearly two decades building Customer Success, Sales, and Account Management teams—and she believes the biggest mistake most CSMs make is thinking they're only responsible for the customer. Great Customer Success Managers manage the entire game.** We talk about why "the customer is always right" creates weak Customer Success, what separates good CSMs from great ones, the underrated skill of managing your manager, and the leadership lesson Erica learned after getting cut from her freshman soccer team at fourteen. Plus: why the best CSMs stop checking boxes, start thinking like owners, and treat every customer relationship as part of a bigger team strategy. Erica Phelps is a Customer Success Executive with leadership experience across Customer Success, Sales, and Account Management. 🔗 Connect with Erica on LinkedIn: https://www.linkedin.com/in/ericalphelps/ — Customer Success Therapy is hosted by Alexandra Sagaydak. 🔗 Follow Alexandra on LinkedIn: https://www.linkedin.com/in/alexandrasagaydak/ Join the AI CS Hub: https://aicshub.com/ 1:1 coaching for CSMs and CS leaders + consulting for B2B SaaS: https://calendly.com/ai-cs-hub/coaching-session

  6. 22 Jul

    Oscar Hackett: Why Every Customer Success Leader Needs a Founder's Mindset

    Oscar Hackett spent years building sales and CS teams from scratch as Head of Sales and Customer Success across VC-backed SaaS companies, before co-founding Kulu, an AI onboarding agent — and he says most CS teams are missing one specific thing: a founder's mindset. We talk about why salespeople are like rivers and always take the path of least resistance around a broken handover, the exact two-rule system that fixed Sales/CS handoffs for good, the one question that fixes almost any cross-team conflict, and why he thinks the CSMs who add real value are about to get paid more than ever — while the ones doing pure tickboxing work will struggle. Plus: the moment that changed his mindset from employee to owner, and the mantra he still runs by — be patient with results, but very impatient with the actions required to get them. Oscar is the Co-Founder and CCO of Kulu. 🔗 Connect with Oscar on LinkedIn: https://www.linkedin.com/in/oscarhackett-44007827 — Customer Success Therapy is hosted by Alexandra Sagaydak. 🔗 Follow Alexandra on LinkedIn: https://www.linkedin.com/in/alexandrasagaydak/ Join the AI CS Hub: https://aicshub.com/ 1:1 coaching for CSMs and CS leaders + consulting for B2B SaaS: https://calendly.com/ai-cs-hub/coaching-session

  7. 16 Jul

    Markus Rentsch: You Can't Have It Both Ways - Own Revenue or Stay "Glorified Support"

    Markus Rentsch spent five years telling Customer Success the thing it doesn't want to hear: you can't refuse to own revenue AND complain about being called glorified support. You can't have it both ways. We talk about the backlash from salespeople ("I poked the bear"), why the average CS leader survives just 18 months, how the first generation of CS tools trained the whole industry to optimize health scores instead of outcomes, and the exact language for pushing back on your CEO - in revenue, not QBRs. Plus the question every CSM should be scared of: do you KNOW your customers are successful, or are you assuming? Markus is the founder of Remarkable - subscribe to his newsletter for the Customer Success Operating System: https://the-csm-operating-system.beehiiv.com/ Connect with Markus on LinkedIn: https://www.linkedin.com/in/markus-rentsch-customer-value-led-growth-for-saas/ — Customer Success Therapy is hosted by Alexandra Sagaydak. Follow Alexandra on LinkedIn: https://www.linkedin.com/in/alexandrasagaydak/ Join the AI CS Hub: https://aicshub.com/ 1:1 coaching for CSMs and CS leaders + consulting for B2B SaaS: https://calendly.com/ai-cs-hub/business-obsessed-csm-strategy-session-clone

  8. 2 Jul

    Tom van Os: Burnout, ADHD & Owning Revenue in Customer Success

    Customer success burnout is the thing everyone feels and nobody names. Tom van Os ran CS teams at Criteo through platform migrations, understaffed quarters, and relentless targets — and burned out in 2019. In this episode he breaks down what really caused it: fixing symptoms instead of systems, people heroics over structural change, and an ADHD diagnosis he only received two months ago. Alexandra and Tom get into: • How to challenge your boss without whining — build the business case, bring the data from every team • Why customer success is now expected to own revenue (NRR, GRR, forecasting) when nobody trained the team for it • The AI-readiness questions every CS leader should answer before buying another tool • Turning an ADHD diagnosis from a perceived flaw into professional positioning • Building a team culture where neurodivergent people do their best work • Why following your gut beats staying in a role that's wrong for you Tom van Os is the founder of WHYS Operating Partners — strategic advisor, trainer, and coach for post-sales teams. Hosted by Alexandra Sagaydak.

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About

🎙 Customer Success Therapy — with Alexandra Sagaydak. The CS podcast that isn't about frameworks, metrics, or revenue plays. I'm Alexandra Sagaydak. After 10 years operating in CS, I got tired of conferences where everyone says the same five things and nobody says what they actually think. So I built this. Every episode, I sit down with a CS, SaaS, or GTM operator and we get into the stuff they don't put on LinkedIn — the decisions they second-guess, the moments they almost quit, the takes they only share after a glass of wine. The guest is the star. The conversations are honest. The therapy is mutual. We listen and we don't judge.

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