The art of raising prices — and keeping customers

Hi there,

Ever felt that sinking feeling when your internet provider quietly increases your bill mid-contract? You’re locked in, annoyed, and already thinking about leaving.

It always amazes me how badly they handle it. No context. No value-add. Just “here’s your new price.”

And yet, big corporations can get away with this. They expect a wave of churn — it’s baked into the forecast.

Scale-ups don’t have that luxury.

Handled badly, a price increase can undo years of trust and momentum. Handled well, it can reinforce value, deepen loyalty, and fund the next phase of growth.

Here’s what smart product teams do differently.

1. Analyse usage before you announce

Not every customer sees your product — or your pricing — the same way. Remind them of the progress your product helps them make.

Think in cohorts: low-usage (high churn risk), core users, champions, and enterprise clients. Each group needs different messaging, timing, and offers.

Test the change first with a small, representative cohort. Measure churn and sentiment before rolling out wider.

And for loyal customers, consider grandfathering or grace windows; legacy pricing for a few months or until renewal.

2. Pair pricing with progress

A price increase should never arrive in isolation. Align it with your roadmap — new features, performance improvements, reliability gains.

Give customers a clear story: your investment funds the things you’ve been asking for.

That alignment reframes the rise as partnership, not punishment.

3. Arm your team for tough conversations

Your CX and sales teams are the front line. Equip them with a simple objection-handling sheet: 

1. why prices are changing,

2. what value has been added, and

3. how to help our customers choose the right plan

A confident, informed response builds far more trust than a hesitant deferral “I’ll check with my manager” every time.

4. Communicate early and clearly

Announce the change well in advance, ideally with options. Show side-by-side plans and the added features or improvements.

A good pricing message has five ingredients:

Cost clarity (what’s changing),
Value proof (what’s been added),
Fairness principle (why now),
Choice (their options), and
Support (how you’ll help).

Let people decide, not react. Transparency builds loyalty.

Also, before going live, test your messaging internally.

Run drafts past your team or a few loyal customers to catch positioning issues, and to make sure it lands as intended.

5. Accept that some churn is healthy

Even with perfect messaging, some customers will leave. Don’t fight it - learn from it.

Capture their reasons, look for patterns, and feed that back into product and pricing decisions. Often, the exit interview reveals more about market-product fit than the onboarding survey ever could.

Price changes done well remind customers you’re investing in their progress, not just your revenue.

Treat the change like a feature launch: plan it, test it, communicate it, and promise fairness at every step.

Do you have a price rise coming up? How are you preparing your team and your customers for it?

Speak soon,

Peter

P.S. Did someone forward you this email? Was it helpful? Sign-up here.