Jason M. Lemkin gives concise, practical guidance for the ideal order and timing to hire first VP-level leaders in a growing startup. He recommends hiring a VP of Marketing early (even around ~$200k ARR/20k MRR) because a strong head of marketing can quickly increase leads and pay for themselves; a VP of Sales once sales processes are repeatable (around $1M ARR, when two AEs hit quota); a VP of Customer Success near ~$2M ARR when renewals/upsell are repeatable; a VP of Product as complexity grows (suggested around $4–6M ARR or when the product has >60 workflows); and a VP of Engineering when you need to hire the next ~10 engineers.
Chapters
I was meeting with a great founder the other day who just crossed a million in ARR and had two great VP candidates and didn't know which to hire. My answer was of course hire both if you can find them. But I thought it might be going through a quick guide in an ideal perfect world that we don't exist in what order to hire your VPs in? Well the first one that's the easiest, even though it's the least intuitive of us, is the VP of Marketing. If you think about it for a minute, even at 20k mrr, call it 200k in AR, 200k in revenue. If you hire a great head of marketing and she tilts the curve, she gets you 20% more leads. Helps manage that funnel 20% better. She will more than pay for herself. And the great first heads of marketing are usually pretty self sustaining. They can jump in, they can deploy HubSpot or marketo, they can get intercom going, they can do the drip campaign with mailchimp. Whatever it takes they're off to the races. So usually this is your easiest and simplest hire as a head of demand gen or a VP of growth hacking number one. The second one is your VP of sales and I think we figured this one out. Don't hire it until the process is at least somewhat repeatable. So Ideally at least two AES, two sales reps that are hitting some sort of quota and then he or she the VP can take you from rep number three to 300. So usually it takes you until about a million in ARR to find to get there to where you have two reps that hit quota. Then customer success. Well we all strongly believe to hiring customer success early, but there usually needs to be enough repeatability, enough corpus of customers before you hire ahead of customers customer success. You can hire a customer success manager the day you incorporate, but usually it takes until close to about 2 million in revenue until there's enough repeated enough renewals, enough upsell to have gone under the bridge to hire a VP of CS. So maybe 2 million VP of product. Trust me, earlier than you think. As soon as the product has more than 60 workflows, as soon as it's too complicated, typically 4 to 5 to 6 million AR and VP of engineering. My rough rule is as soon as you have to hire the next 10 engineers, most ctos and hackers can do the first 10 but after then it's a recruiting and management job and you better have your VP of engineering to hire engineers 11 through 100. But again if you find too early. Hire them both.
