Designing a Proactive, Automation-Led Success Motion

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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🔗 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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