Dear SaaStr: What is The Biggest Difference Between Running a 10 Person Startup and a 100 Person Startup?

The biggest structural difference is you have to hire all the VPs by employee 50–100.

You won’t be able to scale this far without a full management team — VPs of Sales, Marketing, Product, Engineering, Customer Success at least.

But the toughest personal challenge for many CEOs is letting go.

By employee 100, you have to let go of things. You have to let go of being the product manager and head of product.  You have to let go of what you say being almost divinely correct.  You will have to let marketing do things you don’t think will really work, and let sales hire folks you wouldn’t yourself buy from.

You have to let go of the many mistakes that will be made — so long as you hire great VPs to run the playbooks. You have to let go of the fact that some important things will be done “worse” than if you were doing them or managing them yourself.

You have to let go, and learn to backfill the team you build.

Having said that, you can’t let totally go in some areas.  Especially where you don’t truly have a Great VP.

A top mistake I see so many founders make as they scale is letting go in areas they didn’t really hire a great VP in.  Especially, I see founders step out of sales entirely once they hire a merely “OK” VP of Sales.  One that never really understands the space, the competition, and the product.  I almost always see sales quickly fall in that case.

You backfill the great ones.  Other than that, you mainly get out of the way.  But if you hire a mediocre VP — you probably will need to remain deeply engaged in that functional area.

(VP of Nothing image from here)

A related post here:

What Your First 100 Hires Will Look Like

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