Real progress in AI comes from steady habits

Chapter 001

Weekly journal – Helping you learn from the best minds building AI into Customer Success.

Worth the Detour

I just landed in Dublin for Pulse Europe, where 1,000+ retention leaders will get together for a few days. But before conference week kicks off, I made a detour to Glasgow to visit an old friend I met twenty years ago. I was at Columbia; he was at the University of Glasgow. We were part of a small entrepreneurship program helping Scottish businesses write business plans. Two decades later, we live in different countries, work in different fields, and operate on opposite time zones, yet somehow we’ve stayed close.

This trip was special because I finally met his daughter. He missed my wedding this summer because his wife was about to give birth, and sitting in their living room in Scotland before flying to Dublin, I was reminded that the best part of every reunion is how easily you pick up right where you left off.

That same feeling is what makes Pulse special. It’s not the presentations or panels, it’s the people. The old friends you run into in the hallway, the new ones you meet over a cappuccino.

If you can’t make it to Dublin, you can still be part of it: both keynotes will be livestreamed.

👉 Day 1: Your Next Chapter of Retention

👉 Day 2: Building Retention Strategies That Last

I’m also looking forward to the six [Un]Churned podcast interviews happening this Wednesday – in the middle of the Expo hall! Can’t wait to share those once we’ve edited them. Whether in Scotland, Dublin, or wherever your customers take you next, it’s a good reminder that the relationships you nurture – personally or professionally – are what make it all worth the detour.

While the team and I work on these upcoming [Un]Churned episodes, read on for insights from last week’s conversations 🎤

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Small Habits Win Big in AI Adoption

I’ve noticed a trend forming in my [Un]Churned chats lately: teams are testing AI, not transforming with it. The rollouts are big; the results, less so.

As companies shift from SaaS to RaaS (Retention-as-a-Service), success depends on what sticks. The ones winning right now aren’t necessarily moving faster. Instead, they’re getting more consistent. Small habits, repeated over time, are driving big outcomes.

AI Rewards Focus and Consistency

Why Your Ideal Customer Profile Is Broken and How AI Can Fix It ft. Mark Roberge (Co-Founder of Stage 2 Capital)

Mark shared a perspective that stuck with me: most companies still define their Ideal Customer Profile by what’s easiest to sell, not who’s most likely to succeed. His take? AI gives us a chance to fix that. By using data to continually recalibrate around lifetime value and retention, we can stop chasing short-term wins and start focusing on the customers who actually thrive.

🎧 Listen here

A Simple Habit That 3x’ed AI Adoption Rates: The 15-Minute Rule ft. Cat Valverde (Enterprise AI Group)

Cat took that same principle – that focus and consistency beat speed – and turned it into an adoption framework enterprises can actually use. Her 15-Minute Rule asks managers to guide teams through four simple weekly steps, from clicking around to sharing wins. It’s psychology meets productivity: lower cognitive load, build social proof, and adoption follows. One client went from 20% to 80% usage in a month.

🎧 Listen here

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The Coming Retention Reckoning

I just read a piece by Cassie Young at Primary Venture Partners that every CS leader should spend some time with: Tech is on the Brink of a Gross Retention Apocalypse & a Customer Success Renaissance

“It may not be 90 days from now, it may not even be six months from now, but the gross retention apocalypse is 100% coming.”
–Cassie Young, General Partner at Primary Venture Partners

Cassie points to a stat from Menlo Ventures: roughly 60% of generative-AI spending still comes from innovation budgets, not operational ones. Innovation budgets fund experiments; operational budgets fund scale. That gap, she argues, means a lot of companies aren’t sitting on recurring revenue, they’re sitting on borrowed time.

Just as lower switching costs made customer success indispensable during the on-prem-to-SaaS transition, AI is about to do the same thing again. Products are easier to buy than ever, and that means they’re easier to replace. Cassie’s advice is to stop optimizing for net retention alone and start paying closer attention to time to value and time to expansion. If customers aren’t expanding within the first year, odds are they’re not renewing in the second.

The companies that survive this next wave won’t treat customer success as a function, they’ll treat it as their operating philosophy. Because when buying is frictionless, so is leaving. Worth your time to read – especially if you believe Customer Success is due for a reinvention.

Closing Out This Week’s Chapter

If there’s a theme across all three stories, it’s this: focus compounds. The teams using AI well aren’t chasing every new use case — they’re doubling down on the customers, habits, and signals that actually drive retention. In a market where switching is easier than ever, the companies that stay disciplined will be the ones still standing when the hype cycle resets.

Until next time...

— Josh

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