There’s a fun — and very lucrative and rewarding — exercise I like to go through with most of the startups I work with.

It’s goes like this:

• First, who’s your largest customer?  OK.
• Now, do you have a prospect in the pipeline that’s somewhat similar?
• You do?  Great.   Now …
• On that deal … go quote twice your highest price ever. Go try to do that.

This is a terrific exercise to drive your deal size up.

It does >not< mean rip off your customer.

What it does force you to think about is providing a true solution to a big problem (more on that here: A Solution Sale Can Capture 3-20x the Revenues of A Tool Sale. With Almost the Exact Same Core Product.).

$1,000 a month is a lot of money for a widget, even if everyone on my team uses it. But $12,000 a year is dirt cheap for anything that solves a true problem. That solves me having to hire an engineer, or 3, to do something. That fixes something broken in my 500+ person org.

Challenge yourself.

Your biggest deal so far is $100k, with Google?

Well … when Facebook comes in as a prospect … ask for $200k. With confidence.  I know you just got comfortable asking for $100k.  But if you’re worth $100k … then either your product today, or some future variant of that product, is worth $200k.  Almost always.

By quoting double, you may have to:

• Build them an extra feature
• Provide better on-boarding
• Improve customer success
• Get more enterprise
• Get that key integration done
• Upgrade your sales team, or at least, add reps with more experience selling larger deals. Build a new integration. Who knows.

You may have to change a bunch of things to get twice what you did on your largest previous deal.  Or possibly — nothing. Either way, you’ll learn.  It’s a journey.

And if you have a true solution, that really makes an impact … you’ll probably get the 2x pricing. At least some of the time.

Once you do it once, level up.  Make 2x the new 1x.  $200k your new enterprise price point, not $100k.  Do that for a little while.  And then.  It’s time to start again.  2x again.

Rinse. Wash. Repeat.

(note: an updated SaaStr Classic post)