7 Questions That Will Increase Your ARR By 10% (Or More)

There are two kinds of Founders:

1. Those who set and forget pricing.

2. Those who treat pricing like a product: always improving and compounding over time.

The second group tends to have better margins, less equity dilution, and enjoy better sleep.

Because pricing is not a set-it-and-forget-it operation. It’s the highest ROI growth lever you have. And it’s a moving target.

Knowing what questions to ask is often a million times more powerful than knowing the answers.

So… here are 7 questions you should ask yourself multiple times a year. Few of these will result in quick wins. All of these require deeper introspection. All of them will help you progress.

1. In the next 12 months, do we want more logos, users, revenue, profit, or better cashflow?

This is the alignment question. Pricing should always support and accelerate the business objectives.

If your goal is logos, you may consider discounting more aggressively or introducing a freemium plan. If the goal is cashflow, incentivise annual deals. Price according to your north star.

👋 Hi, it’s Tjitte Joosten and welcome to Money on the Table, your newsletter for making sense of pricing and packaging. Subscribe to get posts like this delivered straight to your inbox.

2. Does our current pricing strategy support that goal? Or does it serve a different purpose?

This is the reality check. I’ve seen companies offer freemium and heavy discounts while they’re already holding >60% of the market. Once you’re the leader, the goal should shift to profit.

Most pricing strategies are legacies from a different growth stage. Make sure yours fits your current stage and ambition.

3. How do we create value for our customers? Can we build a business case?

This is the value communication test. If you cannot articulate how your product creates measurable economic value, good luck charging for it.

Can you tie your solution to revenue, efficiency gains, risk reduction, or cost savings? More importantly, can your customer? If not, you’re fighting an uphill battle.

4. Are your most successful customers paying more?

This is the value capture test. If your biggest success stories are still on the starter plan, your monetisation model is broken.

Ask yourself: how can we scale our pricing with value creation? What metric defines customer success and can we incorporate that in our pricing model?

5. Who are our top 3 clients and why do we consider them as such?

This is your ICP calibration. Top clients aren’t just the ones who pay the most. They’re the ones who get the most value, show you the path forward, tell you you’re too cheap, and actively advocate for you.

Figure out what sets them apart, then work backward to make your pricing fit customers like them.

6. Do we know what the next deal is for each customer?

This is your expansion path. If you don’t know what "more" you can offer each client, your pricing probably isn't setting you up for expansion.

Every customer should have a next step: a higher tier, a new module, a usage threshold. No next step = no expansion.

7. How does the product roadmap support our pricing strategy?

This is the monetisation flywheel. Are you building features that solve new problems? Or investing in better and faster outcomes? Then you need to incorporate these upgrades in your pricing model.

Too many SaaS and AI companies are feature factories. Successful roadmaps are monetisation engines.

You don’t need to change your pricing every quarter. But you do need to question it.

Start with questions. Answers will follow.

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