When to hire your first VP of Sales

When to hire a VP of Sales, what to look for, and what to do in the meantime

Hi friends - You are likely receiving this email while I am at the beach 😎. Miami life is good.

So far this month we’ve covered when to hire an SDR and an AE.

Next up - VP of Sales.

And man is this one hard. I’m sure many of you know…there is a very high failure rate with this role in the startup world.


  • A VP of sales is not who you hire to kickstart sales for your startup. It’s who you hire once you have a repeatable process* AND proven success to recruit and manage the ‘rinse, repeat, optimize and expand’.

  • There are 48 different types of VP of Sales - get super clear on which one you need and do not compromise.

Let’s “double click” on these points as some venture bros say. 🤓 

When to hire your first VP of Sales

What are the key responsibilities of a VP of Sales?

Depending on which of the 48 types you choose, based on your maturity, they may or may not be able to do, or own, all of these things.

At a minimum, they should be able to do 1-3.

  1. Recruit top talent

  2. Ramp top talent through training and coaching, an expert on sales tactics

  3. Close deals - helping their reps close deals and closing some of the more complex or larger deals on their own

  4. Sales strategy - when to go up market, what markets or segments to expand into next, etc

  5. Sales enablement and ops to continually optimize your tech and processes to improve conversion rates and shorten deal length

  6. Working closely (and well) with marketing to maximize demand gen success and conversions

If they can’t do 1-3, they are not the person for the job. A VP of Sales primary job should be to build the team and make sure the team closes deals.

If you can find a unicorn who can do all 6 well, and you can convince them to join your startup, you hit the lottery.

But the people who can do all 6 well are really hard to find and to recruit, especially people who can do all 6 well AND have experience at your stage, ACV, etc.

Which means…

  • You (founder) might need to continue to own 4 (strategy) until you have a CRO (especially because there is likely a heavy coordination needed with product and dev priorities and resources)

  • And you might need to hire a fractional or full-time resource to help with 4 + 5 and 6

When should you hire a VP of Sales?

Not before you have a repeatable, successful sales process running with 1-2 AEs already (preferably 2).

Until you do…you (founder) need to be the VP of Sales, again perhaps with the help of a fractional exec and/or your marketing person.

I know…it’s possibly painful to think about continuing to be so intimately involved with ALL the other hats you’re already wearing.

But it will be MORE painful to hire for this role too soon and waste time + money on a hire who could* only cause you to lose momentum and revenue. And then you’ll have to do it anyway…with less money and energy.

What other support options do you have in the meantime?

  1. Work with a recruiter to hire your AEs. If you do this, I’d recommend you look for one who specializes in sales hiring. Ping me if you’d like names.

  2. Hire a fractional CRO/VP of Sales/RevOps to help you with “Make it Repeatable”. Someone who can help you write the playbook and scripts, help you train and coach your AEs, and assist with sales enablement and RevOps initiatives.

When I was a VC, this was the #1 thing I watched founders get wrong - sales hiring. And I get it. It’s really freaking hard.

Founders are amazing sellers because it’s your baby, your passion, you’re a natural even if you aren’t a ‘sales’ person.

Extracting and productizing your founder magic is an art. Building a repeatable process supported by the right tools and assets is a lot of work.

Make sure your sales process is defined and repeatable BEFORE you try to scale the team with a VP of Sales. If you can find that unicorn, snag them. If not, I highly recommend a fractional exec to guide you and support you in the ‘make it repeatable’ process.

Aren’t you just biased because you’re a fractional exec?

You could argue that. But if you know me, you know I am a straight shooter. I suck a lying and I hate wasting anyone’s money or time (including mine).

I truly believe most* fractional execs ARE THE UNICORNS. They are the people who got fed up with the system and built their own. They run their own business - taking full accountability and risk over their income. They have enough of a track record and enough of a network to survive on their own.

That AND they’ve done the ‘make it scalable’ play multiple times. You’ll be hard pressed to find a full-time unicorn, around Series A, who has done it multiple times, or who even wants to do it multiple times. It’s a grind.

Food for thought…from the bottom of my brutally honest heart. ❤️ 

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That's all for now! 

With love and gratitude, 

Jess Schultz

Founder & CEO

Amplify Group