Start Earlier - #8

This week is about anticipating value, not chasing it. From pre-emptive retention to product-led selling and the builders shaping what’s next.

Author

Ross Chapman
May 30, 2025

By the time the churn hits, it’s too late.

By the time AI replaces your role, it’s already been trained.

By the time your product feels average, the user’s already gone.

This week’s signals are a call to move upstream — in how we retain, how we sell, how we price, and how we build. The shift isn’t about reacting faster. It’s about seeing patterns sooner, asking better questions, and claiming your edge before it erodes.

Inside:

  • 🧲 Personalised cancel flows that re-engage instead of apologise

  • 📦 Why productising services doesn’t mean fixed pricing

  • 🎯 What “product creators” will build that PMs can’t

  • 📉 And a reminder: retention isn’t about discounts — it’s about belief

Speed is table stakes.

Starting earlier? That’s the signal.

Let’s get into it 👇

🔗 Signals this week

What if your cancel flow wasn’t a loss point, but a retention engine? Lilly Hanscom shares how she redesigned WeightWatchers’ cancellation experience using behavioural insights and AI, turning disengaged users into revenue savers.

The result: a 300% lift in retained revenue, with offer acceptance up from 18% to 27%. This is one of the sharpest examples we’ve seen of AI used with empathy—and impact.

My take:

  • Most cancel flows are defensive. This one went on offense—with respect.

  • “Financial” reasons usually mean value mismatch, not budget. AI can’t fix that, but a reminder of unrealised value can.

  • Re-engagement isn’t the same as shame or pressure. The win here was clarity: here’s what you’ve used, here’s what you haven’t, here’s a smarter offer.

  • Multi-armed bandits aren’t just for ads. This use of AI learned over time what worked for each user segment and proved that automation can scale empathy if trained right.

  • A perfect example of product-led growth meeting behaviour-led retention.

Blair Enns has done a full 180. Once sceptical of productising services, he’s now urging experts to move quickly, before AI destroys the last scraps of time-based pricing.

But his advice comes with two caveats: don’t price the product, price the client. And never skip the value conversation.

My take:

  • AI is killing “done-for-you” as a standalone value prop. Packaging makes sense, but pricing still needs to flex with value.

  • Most people conflate productisation with fixed pricing, but the sweet spot is standardised delivery, customised pricing. That’s where margin lives.

  • The Value Conversation is non-negotiable. Don’t just hear the client. Understand what the work is worth to them.

  • Productised services make salespeople lazy. You start pitching the box instead of diagnosing the problem. Blair’s framing is a sharp reminder that the real power isn’t the product—it’s the perspective you bring.

  • For soloists and small firms, this is a permission slip: yes, productise your offers- but keep pricing dynamic and human. That’s the leverage play.

Most teams are overwhelmed by AI hype. Endless tools. Conflicting advice. No clear path to value.

That’s why I’ve created the AI Use Case Jam: a focused, 90-minute session to uncover one high-value AI opportunity inside your team, fast.

  • No fluff

  • No theoretical decks

  • Just one practical use case you can act on now

It’s built for product, ops and innovation leaders who want clarity - not another six-month strategy deck.

£950. One session. Big clarity.

Book a Jam or grab a slot — I’m running a limited number each month.

Marty Cagan makes a clear call: product managers who don’t build are being left behind. The future belongs to product creators - high-agency individuals who take responsibility for value, viability, and real outcomes.

With AI reshaping roles and tools levelling the field, this is a redefinition of what product leadership actually means.

My take:

  • This is a wake-up call. Not just for PMs, but for entire orgs: facilitation isn’t creation. Coordination isn’t contribution.

  • The title’s irrelevant. What matters is who’s actively shaping the product - challenging assumptions, managing product risk and pushing value forward.

  • Tools like ChatGPT and Claude are removing the excuse of inaccessibility. You can prototype, validate, spec, test - all in hours. That power requires product sense.

  • The new edge is agency. Designers, engineers, founders - anyone who can move between insight, execution and decision is now fair game for the “product creator” role.

  • This shift doesn’t replace collaboration. But it does shift the centre of gravity to those who own the outcome, not just the process.

  • If you’re a “non-creator PM,” the time to pivot is now. Not just to save your job — but to stay relevant in what’s clearly becoming a builder’s market.

💡 Build on this

“If you’re working on retention, my advice: Start earlier. Treat cancellation as a chance to re-engage, not just retain. And if you’ve got AI in your stack, use it with empathy.”

– Lilly Hanscom, Growth designer, lateral-thinker and product strategist.

Carrying on with Lilly Hanscom’s fantastic piece.

Most cancel flows feel like a bureaucratic process: sterile, transactional, indifferent. They’re designed to reduce churn, but they rarely reconnect with the user. Lilly’s approach flips that — and offers a broader provocation: what if retention isn’t just a metric, but a moment of care?

Here’s the deeper truth: by the time someone’s cancelling, they’re not just lapsing in usage - they’re lapsing in belief. It’s not about the price. It’s about whether they feel seen, understood, and supported.

And that’s where AI should shine.

Instead of using AI to automate friction, use it to surface relevance. Remind people of their intent. Reflect back their progress. Reframe what’s next. That’s how you re-engage, not just retain.

What if your cancel flow was the most empathetic moment in your product?

In a world optimising for growth, the real unlock might be this:

Start giving a damn just as someone’s about to leave.

So, what are you going to start earlier?

📬 From the feed

What do I do? I help founders and teams build smarter businesses faster. Take a look at previous work and what that could look like on my website.

📲 If you liked this and spend most of your time on LinkedIn, then consider giving me a follow @ross-chapman.

🔚 Until next week…

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