Jason Lemkin谈招聘首位销售VP的8条建议，2名销售达标是启动时机

Dear SaaStr: What Are A Few Top Tips to Hiring The Right First VP of Sales?

Hiring a great first VP of Sales is one of the most critical decisions you’ll make as a founder. Get it right, and they’ll scale your revenue and team. Get it wrong, and you’ll lose a year. Or more.

"When is the right time to hire your first VP Sales?

Only once you have 2 sales reps really hitting quota.

One you have 2, you're ready to hire a VP Sales to scale you from reps 3-300." pic.twitter.com/hqPgunv5xU

— Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) October 6, 2026

Most of the failures come from the same handful of mistakes. Here’s what I’d do.

#1. Wait Until You Have 2 Reps Hitting Quota

Two, because one rep hitting quota can be a fluke. Two means you have something at least sort of repeatable. That usually happens around $1M to $2M in ARR.

Until then, you are the VP of Sales. Close the first 10 to 20 customers yourself. Hire the first 2 reps yourself. A VP of Sales takes something that is sort of working and makes it work at 5x the scale. They can’t invent it for you. Hire one before there’s anything to scale and you’ll pay a VP salary for someone to tell you that you don’t have enough leads.

#2. Hire Someone Who Has Already Worked at the ARR You’ll Be at in 12 Months

There are 48 types of VP of Sales, and it starts with four stages:

The Evangelist (pre-$1M). Great at the first few deals. Can’t build a team.
Mr. or Ms. Make-It-Repeatable ($1M to $10M). This is the one you want.
Go Big ($10M to $40M). Scales a machine that already runs.
Dashboards ($40M+). Manages managers and reports to the board.

The big-logo candidate from Salesforce or Oracle is almost always a Go Big or a Dashboards. They joined at $30M and rode it to $150M, with a brand, inbound leads, sales engineers, sales ops and an enablement team. You have none of that. They’ve never seen a company that looks like yours, and they’ll spend 6 months asking for resources you can’t afford.

Then match deal size. A VP who has only sold $250K deals will be lost at $15K, and the reverse is just as true.

#3. Ask “Who Do You Know Right Now Who Would Join You?”

A great VP of Sales does five things, in this order: recruiting, helping reps close, sales tactics, sales strategy, and last, selling deals themselves.

Recruiting is first because nothing else on the list scales without it. You’ll need 8 to 10 good reps in the first year, and you can’t recruit them. They can.

So ask for names. A real VP of Sales has 2 or 3 reps who will follow them anywhere, and one of them should start within 30 to 60 days. If nobody wants to come with them, they aren’t ready to be a VP. Then ask who they personally hired at their last company. Inheriting a team doesn’t count.

#4. Make Them Demo Your Product. Yes, Really

Give them a week and have them demo it back to you. It won’t be perfect. You’re checking that they did the work and that they can explain why a customer should buy.

Your first VP of Sales will be in deals every day with a team of 3 or 4 reps, so there’s no room for a leader who only manages from a dashboard. A VP who needs a sales engineer for every call can’t coach your reps either. Ask yourself one more thing after the demo: would you buy from this person?

#5. Ask “What Will Revenue Look Like 120 Days After I Hire You?”

There are two bad answers. The first is “we’ll double it.” That’s someone who hasn’t done it at your stage, or who tells CEOs what they want to hear. The second is “I’ll need a couple of quarters to assess.” That one’s a Dashboards.

The good answer starts with questions back at you. How long is the sales cycle? How many qualified leads a month? What does each rep close today? Then you get a real number tied to your funnel.

A few more questions that work:

How big a team do you think we need right now?
What deal sizes have you sold?
Tell me about a deal you lost to a competitor.
How should sales and marketing work together at our stage?

#6. Ask Which AI Agents They’ve Deployed Themselves. And Have Them Show Them To You

This one is new. We run SaaStr with 3 humans and 20+ AI agents in production. A VP of Sales hired in 2026 will be managing agents alongside reps from the first week: outbound, inbound qualification, follow-up.

Ask what they’ve deployed, what they trained it on, and what broke. If the answer is “my RevOps team handled that,” you’ll be doing the work for them.

#7. Start Meeting Candidates 6 Months Before You Need One

Plan on 6 months for the search, often longer. Meet 20 to 30 people. The best candidate is usually the #2 at a company a stage ahead of you: the director who was there from $2M to $20M and is ready for their own team. They aren’t looking, so you have to recruit them.

Starting early also keeps you out of the Desperation VP hire, the one you make because you’re tired of running sales yourself. No VP beats a Desperation VP every time.

#8. Check These 4 Things at Day 30

Revenue won’t always move much in 30 days, although it should at least shortly thereafter. These will:

Did they bring in 1 or 2 strong reps, or have them signed?
Are they in deals, on calls, helping close?
Are your existing reps getting better?
Do you feel relief, or do you have more work than before?

After that, revenue per lead should go up inside one sales cycle. If it hasn’t after a full cycle, it won’t. Make the change then. Founders who wait 9 months hoping it turns around lose the year.

The 5 Checks Before You Send the Offer

Two reps are already hitting quota.
The candidate has worked at a startup at the ARR you’ll hit in 12 months.
They named 2 or 3 reps who will join them.
They demoed your product and you’d buy from them.
Their 120-day number came from your funnel math.

If one of these is missing, keep looking.

Related:

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More here:

What Makes a Great VP of Sales and How to Hire One: The Complete Guide