Debug 003: Validating A Pricing Overhaul

Hey folks! 👋

Welcome to another edition of Debug, where I answer your growth and go-to-market questions!

In Debug 003 I’m answering a question from a founder about to make a drastic shift from fixed team pricing to seat (user) based.

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DEBUG

Jon is the founder and CEO of Userback, about to head into unknown waters with a major pricing change, and asks:

Alright, here we go. This is a big one.

You’re blowing up your pricing model and going seat-based in an competitive market.

Props for making the move - pricing is hard, and a bad value-based model hurts literally everything (LTV, CAC payback, churn, you name it).

But your ARPU is set to nosedive from $80 to $30, and you're asking how to validate it properly without surveying existing customers.

First of all: I love that you’re leaning into this.

Pricing is rarely “set and forget” and should evolve with your product and the feedback flywheel.

Far too many founders shy away from this.

So here’s how I’d think about your current situation:

1. Do A Shadow Launch with New Customers Only

Before pulling the trigger across the whole userbase, run your new pricing model in stealth with new customers only. Here’s why:

• It keeps the stakes lower: you’re not risking existing revenue streams while still getting real-world data.

• New customers don’t carry the baggage of your old pricing: they’ll evaluate you against the market and the value they get.

You can offer existing plans side-by-side with the new seat-based plans for inbound leads.

Position the old model as “legacy” and lightly steer folks to the seat-based model.

Listen closely: which one do they choose? What questions come up in the sales process?

2. Dig Deep into Expansion Behaviour

Seat-based models live and die by expansion revenue, so it’s critical that you start by modelling your base case:

• What % of accounts do you estimate will expand to 25+ seats?

• What’s the break-even volume needed to match your current ARPU? (e.g. if you’re dropping ARPU from $80 to $30, you’ll need ~3x the customer volume to make up the gap).

Once you’ve got the model, test it.

Use account segmentation with your existing customer base (past deals closed) to gut-check how many of them actually look like high-seat expansion opportunities.

Are you relying too much on “land and expand” success that realistically might not come?

Will the new pricing attract enough new business to offset that?

3. Run Win/Loss Analysis on Deals

You mentioned avoiding a pricing survey but I’d still encourage you to do some form of surveying, even if it’s with non users/customers.

That being said, regardless you should lean into direct, qualitative conversations with prospects in your pipeline.

Every won or lost deal in the upcoming quarter is an important data point for validating your new pricing structure:

• For wins: Ask what about the pricing resonated (“the per-seat model lets us scale incrementally”) and what didn’t (“the minimum 25 seat enterprise plan was a blocker”).

• For losses: Dig into objections. Was their issue pricing-related, or something deeper about positioning?

Your front-line sales or CS teams should uncover these insights daily - make sure they’re documented.

4. Set Expectations to Keep the Value Crystal Clear

Making a big pricing shift - especially one that charges less - gives you an opportunity to reposition as the most logical, high-value choice in your market.

But... lower pricing always comes with risk.

Without a clear framework that ties each tier directly to its benefits, you run the risk of customers undervaluing your tool entirely (or assuming they can haggle for discounts).

Here’s how you might anchor the value and validate if customers are willing to pay what you’re asking:

• Keep the pricing structure simple and transparent. Free > $10 > $15 > $25 per seat. No hidden fees, no overcomplicating the tiers.
  

• Position each tier as solving a specific job-to-be-done for distinct user roles. For example:

  • Free = for hobbyists or small teams trying out feedback workflows.

  • Paid = for PMs scaling structured feedback loops within teams ($10-$15).

  • Enterprise = managing feedback at an organisational level with SLA escalations, advanced integrations, and reporting ($25+).
    

• Tell a story of growth across the tiers. Make it clear how starting small can expand smoothly into more valuable territory. The $10/user tier gets teams started with triage workflows, while $25/user unlocks collaborative reporting and advanced capabilities. This makes the pricing feel like an investment that scales with their team’s needs

When in doubt, focus on clarity and relatability.

If your pricing tiers clearly map to outcomes that resonate with real user pain points, you’ll avoid a “race-to-the-bottom” trap.

Final pro-tip: When you have conviction in the model through early testing as above, make this a cheer-worthy event to your community. Share why you’re making the change and position it as a deliberate mission to align outcomes with how people pay. It won’t just justify the adjustment; it’ll establish trust (critical for your future pricing experimentation).

Communication can absolutely be the difference between a pricing change being well received or it being slated.

Hope that helps!

THAT’S A WRAP

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Until next time!

— Ben

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