One of the top engineers at Adobe Sign / EchoSign, who had strong experience both in consumer internet and enterprise internet, told me a while back the #1 reason he disliked SaaS / enterprise — it never gets easier.  His point was, once you solve the problems for Big Customer #1, then you get 10 more Big Customers.  Which is ten more problems.  Then 100 more customers.  That’s 100 more problems.  It gets worse, not better.

A fair point for the dev team.

And in some ways, it’s also true for a VP of Sales.  No matter how well a startup is doing — you always have to hit a bigger number next quarter and next year.  You sort of never get a break as a VP of Sales.

But one of my top learnings from all the other SaaS start-ups out there: for the founders — it gets easier.  Not easy, but easier.  Once you get past 50 employees, it gets a lot easier.  Once you break through $10m in ARR, it gets even easier.  And once you break through about $15-$20m in ARR, it gets really, a dramatically whole lot easier.

It’s not that it gets any easier to grow, or hit your plan, or make your investors happy.  That stays just as hard.  And competition gets harder as you cross this point – your competition sees it, and tries harder.  And more enter the space.

But the day-to-day operational pain in SaaS companies seems to go away around $10m-$15m in ARR, depending on how each is structured, capital needs, etc.  At that point:

  • Your customer base becomes more diverse, and not dependent on any whales.
  • You have enough reference accounts.  You want more — but don’t need more logos, as great as they are.
  • Your sales and client success teams are working as a team, as an imperfect but effective engine, and not dependent on a single rockstar or two.
  • You hopefully have a real management team that can own each functional area.  Or at least, you are close to that.  A bit more here.
  • You have a brand, maybe a small brand at first, but a real one.  This is a key inflection point in the getting-easier process.  More leads come in, more easily.  Customers still need to be sold, for sure, but at least you don’t have to kill yourself just to get into the discussion.  More here.
  • You can’t be killed by BigCo entering the space or the competition.  Wounded, yes.  But not killed.  More here.
  • Your product may still be rough in a lot of places, but it becomes pretty feature-rich.  You have what many customers need.  And this also starts to become a moat vs. other smaller entrants.
  • You know the market so well, it’s pretty easy to see 2 years out, not just from a product side, but from a scaling revenue and team side.  Makes hiring much easier.

So to my SaaS sisters and brothers out there, working to get to the first $1m in ARR, or $5m in ARR, or $10m in ARR, or $20m in ARR, my #1 learning and piece of advice.  Yes, you’ll have to put another plate (or two) on the bench press every 6 months (or insert whatever metaphor you prefer here).

But —  It Gets Easier once you can’t be stopped.  Not easy, but easier when you reach the Inevitable phase.



(Note: an updated SaaStr Classic post)

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