For: Founders with real revenue and a price they set years ago

What should I charge, and how do I raise prices without losing customers?

Where the line actually sits

3 options

How many packages to offer

Most buyers aren't deciding whether to buy, they're deciding which one. Build the middle one as the thing you actually want sold, and let the other two do their job.

90 days

Notice before an increase on existing accounts

Long enough that nobody feels ambushed, short enough that it doesn't become a negotiation. One paragraph, the real reason, no apology.

6 months

How often to revisit the number

A price that never moves is a decision you made when you knew the least about what you were worth.

Scope, not discount

What to move when the price is too high

Take something out rather than money off. Buyers remember the discount at every renewal, forever. They don't remember the scope line.

What changed in the last year

• Per-seat pricing is breaking. If your customer's headcount falls while the work they do grows, seat-based revenue shrinks in a year where you delivered more value than ever. Any business where getting faster or cheaper to deliver makes you less money is selling the wrong unit.
• The cost of delivering fell, and buyers know it. Cost-plus pricing now invites a conversation about your margins that you will lose. Value pricing is no longer the sophisticated option — it's the only defensible one.
• Outcome-based and usage-based pricing moved from experimental to normal in the last eighteen months, which means your buyer has almost certainly signed one and will not find it strange.

What most founders get wrong

• “We'll lose customers if we raise prices.”

  The churn you fear almost never comes from the customers you value. It comes from the bottom of the base, the accounts that consume support and complain about invoices. Losing them is the point.

• “We're cheaper, that's our advantage.”

  Cheap is the one advantage anyone can copy in an afternoon, and it attracts the buyers most likely to leave for someone cheaper still.

• “We should price against our competitor.”

  You'd be anchoring to a number someone else guessed. Price against the thing in the customer's budget that goes away when they buy you.

When I'd tell you the opposite

• You are in a genuine land grab where distribution is the whole game and being installed everywhere matters more than margin — price low deliberately, and know the date you stop.
• Your buyer's budget is fixed by someone above them and there is no line item to replace. Then the conversation is about which existing spend dies, and that's a different sale.
• Retention is below 80%. Fix the product before touching the price; an increase on a leaking base just empties it faster.

Related questions

How much should I raise prices by?

If you've never raised them, 15–30% on new customers rarely changes the close rate in any way you can measure. If close rates don't move, you were underpriced and you have your answer.

Should I grandfather existing customers?

For your best accounts, for a defined period, yes — and say so explicitly, because it's a real gift and it buys loyalty. Permanent grandfathering just means you run two businesses forever.

Should I publish my pricing?

Publish it if the buyer can self-serve or if you want to filter out bad fits before a call. Keep it off the page if pricing genuinely varies by scope — but then publish a range, or you lose people who assume they can't afford you.

What do I do when a customer asks for a discount?

Ask what they'd like to remove. It turns a price fight into a scoping conversation, and most of the time they'd rather pay than lose the thing.