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

Oct 20, 2025

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.

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ANECDOTE

70% Of Logos Moved To A Pooled Model

Aircall moved 70% of its SMB logos from named CSMs to a pooled digital model and found the change was challenging.
The abrupt post-signature shift exposed broken handoffs and misaligned expectations set during sales.

ADVICE

Design Digital Success At Acquisition

Start designing digital customer success at acquisition, not just at handoff.
Understand lead source, funnel behavior, and set consistent expectations in sales to avoid broken experiences.

INSIGHT

High-Touch Trials Predict Post-Sale Risk

Heavy salesperson involvement in trials signals the product can't self-serve trial conversions.
Trial conversion issues predict downstream success problems after purchase.

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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
• 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 data

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🎙️ 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/

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🎙️ 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

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