Digital CS, Done The Hard Way w/ Madelyn DePrey Global VP of Customer Success @ Aircall episode artwork

EPISODE · Oct 20, 2025 · 37 MIN

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

from The Customer UnSuccess Podcast · host Joe Di Grande

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 dataIf 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/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

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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 •...

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

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