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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 đ. Miami life is good.
Next up - VP of Sales.
And man is this one hard. Iâm sure many of you knowâŚthere is a very high failure rate with this role in the startup world.
TLDR -
A VP of sales is not who you hire to kickstart sales for your startup. Itâs who you hire once you have a repeatable process* AND proven success to recruit and manage the ârinse, repeat, optimize and expandâ.
There are 48 different types of VP of Sales - get super clear on which one you need and do not compromise.
Letâs âdouble clickâ on these points as some venture bros say. đ¤
![](https://media.beehiiv.com/cdn-cgi/image/fit=scale-down,format=auto,onerror=redirect,quality=80/uploads/asset/file/09c27951-ba49-4e60-8a9e-a7e74900fabd/paul_rudd.gif?t=1715959549)
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.
Recruit top talent
Ramp top talent through training and coaching, an expert on sales tactics
Close deals - helping their reps close deals and closing some of the more complex or larger deals on their own
Sales strategy - when to go up market, what markets or segments to expand into next, etc
Sales enablement and ops to continually optimize your tech and processes to improve conversion rates and shorten deal length
Working closely (and well) with marketing to maximize demand gen success and conversions
If they canât 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 meansâŚ
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 doâŚyou (founder) need to be the VP of Sales, again perhaps with the help of a fractional exec and/or your marketing person.
I knowâŚitâs possibly painful to think about continuing to be so intimately involved with ALL the other hats youâre 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 youâll have to do it anywayâŚwith less money and energy.
What other support options do you have in the meantime?
Work with a recruiter to hire your AEs. If you do this, Iâd recommend you look for one who specializes in sales hiring. Ping me if youâd like names.
Hire a fractional CRO/VP of Sales/RevOps to help you with âMake it Repeatableâ. 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. Itâs really freaking hard.
Founders are amazing sellers because itâs your baby, your passion, youâre a natural even if you arenât a âsalesâ 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 âmake it repeatableâ process.
Arenât you just biased because youâre 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 anyoneâs 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 theyâve done the âmake it scalableâ play multiple times. Youâll 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. Itâs a grind.
Food for thoughtâŚfrom the bottom of my brutally honest heart. â¤ď¸
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That's all for now!
With love and gratitude,
![]() | Jess SchultzFounder & CEO Amplify Group |