Quote double your biggest deal ever, and watch where it breaks
Jason Lemkin's exercise for founders going upmarket: take the next prospect that looks like your largest customer, ask for twice your highest price, and pay attention to what the deal demands of you.
The exercise is one sentence long. Find your largest customer. Find a prospect in the pipeline that looks like them. Quote that prospect twice your highest price ever.
Lemkin, the founder of SaaStr, sets it out in a post on the site. If your biggest customer pays $10,000, ask the next one for $20,000. If your biggest deal so far is $100,000 with Google, ask Meta for $200,000.
The rule he attaches matters more than the number. You do not do this to existing customers. They bought before you had proof, and they get the price they signed.
The point is not the extra money on one contract. It is what the attempt tells you.
Lemkin's argument is that price follows the size of the problem rather than the size of the product. A thousand dollars a month is a lot for a widget that everyone on the team happens to use. Twelve thousand a year is cheap if it removes the need to hire an engineer, or three, or fixes something broken inside a 500-person organisation.
So the doubled quote forces a question the founder has been avoiding: are we selling a tool or a solution? Lemkin's own framing is that the same core product can be sold either way, and that the solution sale captures multiples of the tool sale.
Then comes the useful part, which is the friction. On his account, quoting double may mean building an extra feature, doing a key integration, improving onboarding, strengthening customer success, or hiring reps who have sold larger deals before.
Each of those is a diagnosis. The gap between your current price and twice your current price is a list of the things your company has not built yet, written out by a prospect for free.
Sometimes nothing has to change and the buyer simply says yes. Either outcome is information, which is the whole reason to run it.
Lemkin's staircase for reaching a six-figure deal goes: close $10,000, ask the next similar prospect for $20,000, close it, ask the next for $40,000, and keep going. Once a doubled price closes, it becomes the new baseline and the exercise starts again from there.
He offers one marker for whether you are moving upmarket properly: every quarter, you have a new largest customer.
The honest caveat is in his own wording. You will probably get the doubled price at least some of the time, which is not the same as most of the time.
For a founder, the cost of the test is one deal in the pipeline and the discomfort of saying a bigger number out loud. The return, if the prospect walks, is a specific reason why, from someone with a budget.