Ever felt like you're constantly playing catch-up in customer experience? What if you had an AI assistant working proactively for you, around the clock? In this episode we dive deep into the game-changing potential of agentic AI, specifically highlighting the new scheduling feature within Claude Cowork.

Until recently, true agentic AI was largely reserved for technical experts. But with Claude Cowork, it's now accessible to the masses, allowing you to automate repetitive, insightful tasks – from daily health reports to weekly QBR prep and churn signal digests. Alex explains how this isn't just about simple automation; it's about spinning up a full agentic loop that reads context, calls tools, and adapts its output. While some limitations exist (hello, Mac desktop app!), the ability to schedule recurring, complex tasks in natural language is a massive unlock for anyone in CX. Get ready to shift from reactive to proactive and reclaim your time!

Download our Digital CX Claude Plugin Suite: shop.digitalcustomersuccess.com

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The Digital Customer Success Podcast is hosted by Alex Turkovic

🎬 This content was edited by Lifetime Value Media.
Learn more at: https://www.lifetimevaluemedia.com

Download your CS Claude Plugins: store.digitalcustomersuccess.com

In this episode, Alex dives into a massive shift happening right now in the AI landscape: the move from ChatGPT to Claude. It's a conversation you won't want to miss if you're navigating the rapidly evolving world of AI tools in your CX and CS roles.

Alex shares why Claude is gaining significant traction, particularly for its practical, co-worker-like responses and its advanced functionalities like "Co-Work" and "Skills." We explore how different AI platforms—ChatGPT, Gemini, Perplexity, and Claude—excel in various tasks, helping you decide which tool is best suited for your specific needs, whether it's deep research, image generation, or sophisticated task management.

A highlight of this episode is the introduction of Claude's game-changing features: Co-Work, which acts as a language intermediary for complex projects, and "Skills," customizable actions that automate repeated tasks, from preparing EBRs to generating churn post-mortems. Alex even shares how he built a sophisticated staffing model in just two hours using Co-Work!

Whether you're new to AI or looking to optimize your current stack, this episode offers practical insights and a glimpse into the future of AI co-pilots.

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Like/Subscribe/Review:
If you are getting value from the show, please follow/subscribe so that you don't miss an episode and consider leaving us a review.

Website:
For more information about the show or to get in touch, visit DigitalCustomerSuccess.com.

Buy Alex a Cup of Coffee:
This show runs exclusively on caffeine - and lots of it. If you like what we're, consider supporting our habit by buying us a cup of coffee: https://bmc.link/dcsp

Thank you for all of your support!

The Digital Customer Success Podcast is hosted by Alex Turkovic

🎬 This content was edited by Lifetime Value Media.
Learn more at: https://www.lifetimevaluemedia.com

In this episode, we tackle the ago-old question in digital customer success: how do you gracefully transition customers from ahigh-touch, one-on-one CSM relationship to a scalable self-serve digital motion?

It's a critical challenge as businesses grow and seek to optimize valuable CSM time.

We dive deep into why segmentation needs to go beyond just Annual Recurring Revenue (ARR), exploring additional factors like product complexity and future growth potential to ensure the right customers get the right level of human support.

Discover the prerequisites for a successful digital transition, including the necessity of a robust, self-serve foundation and a smart triggering mechanism to proactively engage customers.

I share insights on reframing the conversation from "what they're losing" to "what they're gaining," and the importance of always providing a human bailout option.

We also touch on virtual QBRs and auto-renewal strategies.

Join me to learn how to prepare your CS motions for digital, keep customers engaged and empower them in a hybrid digital-human experience.

Email Template mentioned in the show: https://docs.google.com/document/d/1SSTLT2iOZ7O271zvJ2n55jHx3MgWrO72IMrSM56HXs4/edit?usp=sharing

Support the show

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Like/Subscribe/Review:
If you are getting value from the show, please follow/subscribe so that you don't miss an episode and consider leaving us a review.

Website:
For more information about the show or to get in touch, visit DigitalCustomerSuccess.com.

Buy Alex a Cup of Coffee:
This show runs exclusively on caffeine - and lots of it. If you like what we're, consider supporting our habit by buying us a cup of coffee: https://bmc.link/dcsp

Thank you for all of your support!

The Digital Customer Success Podcast is hosted by Alex Turkovic

🎬 This content was edited by Lifetime Value Media.
Learn more at: https://www.lifetimevaluemedia.com

Today I’m joined by Stephanie Blair, Founder of Know & Flourish (https://knowandflourish.com/), for a practical conversation on digital career growth in Customer Success. We dig into how to build a career identity (not just a title), why experimentation matters, and how to expand your lane without burning out. You’ll hear a real-world example from my team of turning a scrappy spreadsheet into a lightweight web tool, and what that kind of initiative can do for your brand inside the business.

We also talk about the shift in CS org design: the rise of digital program managers, AI-assisted workflows, and yes - why human, IRL moments still win renewals.

If you’re exploring a pivot into CS (from sales/marketing/product) or within CS (service → expansion, or IC → leader), Stephanie breaks down how to translate your skills, control your narrative, and interview like a peer.

Housekeeping: I’ll be co-chairing the CS Summit in Austin later this month, and the Digital CX Masterclass is coming soon join the waitlist at https://DigitalCustomerSuccess.com/Masterclass to be first in line.

Support the show

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Like/Subscribe/Review:
If you are getting value from the show, please follow/subscribe so that you don't miss an episode and consider leaving us a review.

Website:
For more information about the show or to get in touch, visit DigitalCustomerSuccess.com.

Buy Alex a Cup of Coffee:
This show runs exclusively on caffeine - and lots of it. If you like what we're, consider supporting our habit by buying us a cup of coffee: https://bmc.link/dcsp

Thank you for all of your support!

The Digital Customer Success Podcast is hosted by Alex Turkovic

🎬 This content was edited by Lifetime Value Media.
Learn more at: https://www.lifetimevaluemedia.com

Welcome to episode 100! I’m joined by Chuck Ganapathi, Gainsight’s new CEO, for a wide-ranging, candid conversation about where customer success is headed and what leaders should do right now.

We start with Chuck’s career through four platform eras: mainframe to client/server to cloud to AI - and how those shifts shape strategy. He shares the little-known origin story of “Customer Success” at Salesforce, Gainsight’s early days, and why integrations (Salesforce, SAP CX, Microsoft Dynamics) are never “done”—they’re living systems that demand clean data and constant tuning.

Then we dig into Chuck’s concept of Retention-as-a-Service. In a world where retention is existential, the 80/20 mindset breaks. Every dollar matters, which means every customer matters. We talk agentic AI (augmentation vs autonomy), how a “renewal agent” can cover the long tail, and why the magic is orchestration—letting agents handle the repeatable while humans lean into judgment, relationships, and value.

We close with practical automation stories, a few resources Chuck follows, and a reminder that the human-to-human piece isn’t going anywhere.

Links in Today's Episode:

• Ethan Mollik: One Useful Thing
• Saanya Ojha
• Jamin Ball: Clouded Judgement
• Andrej Karpathy on the Dwarkesh Podcast: AGI is still a decade away

Support the show

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Like/Subscribe/Review:
If you are getting value from the show, please follow/subscribe so that you don't miss an episode and consider leaving us a review.

Website:
For more information about the show or to get in touch, visit DigitalCustomerSuccess.com.

Buy Alex a Cup of Coffee:
This show runs exclusively on caffeine - and lots of it. If you like what we're, consider supporting our habit by buying us a cup of coffee: https://bmc.link/dcsp

Thank you for all of your support!

The Digital Customer Success Podcast is hosted by Alex Turkovic

🎬 This content was edited by Lifetime Value Media.
Learn more at: https://www.lifetimevaluemedia.com

In Episode 99, I do something a little different: I take you behind the scenes as I use ChatGPT in voice mode to design a real automation from start to finish. The goal? Build an internal chatbot for product and engineering that’s trained on CX call transcripts stored in Gong, so teams can ask targeted questions (“What’s frustrating customers in Module X?”) and get instant, concise answers with deep links back to the exact call moments.

You’ll hear how I frame the problem, push the model to avoid hallucinations, and pick a stack that balances speed, privacy, and scale: Gong → Airtable as the searchable store → a Zapier-hosted chatbot for querying. We also cover transcript hygiene (auto-removing small talk and personal details), vendor privacy considerations, and a simple habit hack: having AI remind you later to actually implement the ideas you generated while walking the dog.

I’ll link the step-by-step PDF I asked ChatGPT to generate in the show notes so you can follow along and adapt it to your environment.

If this sparks ideas for your own digital CX programs, follow/subscribe and drop a review—it really helps more practitioners find the show.

Support the show

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Like/Subscribe/Review:
If you are getting value from the show, please follow/subscribe so that you don't miss an episode and consider leaving us a review.

Website:
For more information about the show or to get in touch, visit DigitalCustomerSuccess.com.

Buy Alex a Cup of Coffee:
This show runs exclusively on caffeine - and lots of it. If you like what we're, consider supporting our habit by buying us a cup of coffee: https://bmc.link/dcsp

Thank you for all of your support!

The Digital Customer Success Podcast is hosted by Alex Turkovic

🎬 This content was edited by Lifetime Value Media.
Learn more at: https://www.lifetimevaluemedia.com

In this episode, we dig into a shift I think is non-negotiable in today’s AI-first world: you must become the director, not the doer. Inspired by Dan Martell’s framework, we explore how AI should handle the execution — while you define the outcome, set constraints, and bring the human edge.

I introduce the three pillars that separate average from exceptional direction: Vision, Taste & Care. You’ll hear how I use them in real-world workflows, the traps I fell into trying to do everything myself, and a few tactical moves (prompts, boundaries, feedback loops) that helped me step up.

If you feel like you’re driving but still stuck doing all the work — this one’s for you.

👉 Hit follow/subscribe so you don’t miss future episodes, and if this one lands, leave a review or drop me a line.

Support the show

+++++++++++++++++

Like/Subscribe/Review:
If you are getting value from the show, please follow/subscribe so that you don't miss an episode and consider leaving us a review.

Website:
For more information about the show or to get in touch, visit DigitalCustomerSuccess.com.

Buy Alex a Cup of Coffee:
This show runs exclusively on caffeine - and lots of it. If you like what we're, consider supporting our habit by buying us a cup of coffee: https://bmc.link/dcsp

Thank you for all of your support!

The Digital Customer Success Podcast is hosted by Alex Turkovic

🎬 This content was edited by Lifetime Value Media.
Learn more at: https://www.lifetimevaluemedia.com

After a short hiatus, Alex is back—and he’s bringing some big energy and even bigger ideas to the Digital Customer Success podcast. In this solo episode, he shares a deeply personal and practical reflection on how we can create magical, human moments in our digital programs—at scale.

Inspired by Will Guidara’s book Unreasonable Hospitality, Alex explores what it means to go beyond the expected, whether that’s sending a baby gift, a surprise mouse (the tech kind), or a handwritten note. The kicker? You can use AI and automation to help you spot those moments—without losing the human touch.

You’ll learn:

• Why emotional connection matters more than ever in CX
• How to train your systems (and your team) to spot moments of magic
• Real-world examples you can replicate
• Tools like Gong, Zapier, and Handwrytten in action

If you’re looking for a way to stand out in a sea of digital sameness, this episode’s for you. Subscribe and stick around—we’re just getting started.

Support the show

+++++++++++++++++

Like/Subscribe/Review:
If you are getting value from the show, please follow/subscribe so that you don't miss an episode and consider leaving us a review.

Website:
For more information about the show or to get in touch, visit DigitalCustomerSuccess.com.

Buy Alex a Cup of Coffee:
This show runs exclusively on caffeine - and lots of it. If you like what we're, consider supporting our habit by buying us a cup of coffee: https://bmc.link/dcsp

Thank you for all of your support!

The Digital Customer Success Podcast is hosted by Alex Turkovic

🎬 This content was edited by Lifetime Value Media.
Learn more at: https://www.lifetimevaluemedia.com