When to Hire Your First VP of Sales After Series A

A Series A round changes the conversation in the boardroom. Investors want a repeatable revenue engine, and the most common question founders hear is some version of "when are you hiring a VP of Sales?" It is a fair question. It is also one of the easiest hires to get wrong.

I have been recruiting sales leaders since 1997 and founded Howard Lee & Associates in 2002. Over that time the pattern has stayed remarkably consistent. Companies that hire their first VP of Sales at the right moment, with the right profile, tend to scale. Companies that hire too early, or hire a leader built for a much bigger company, often lose a year. Here is how to think about the decision.

Why the first VP of Sales is so hard to hire

The first VP of Sales at a Series A company is not the same job as a VP of Sales at a public company, even though the title is identical. At your stage, this person usually has to do three jobs at once.

• Player. They will carry or close deals themselves, especially the largest ones.
• Builder. They create the sales process, the CRM setup, the forecast, the comp plan and the hiring plan, often from nothing.
• Leader. They recruit, coach and keep a small team of account executives productive.

Many experienced sales executives are excellent at one or two of these. Few are great at all three, and fewer still want to do all three at once.

Signs you are ready for a VP of Sales

Founders have closed real, repeatable deals

Before you hire a sales leader, the founders should have sold the product themselves to enough customers that you can describe who buys, why they buy and how long it takes. A VP of Sales can scale a motion. It is much harder for them to discover one from scratch.

You have more pipeline than the founders can handle

When good opportunities slip because no one has time to work them, you have a capacity problem that a sales leader can solve.

You are ready to hire several account executives

If your plan for the next year includes building a team of account executives, someone needs to recruit, onboard and manage them. Founders rarely have the time to do that well while running the company.

You need forecasting the board can trust

Once revenue targets are in the board deck, you need someone who owns the number and can explain the forecast with confidence.

Signs it may be too early

• The ideal customer is still changing. If you are still testing which segment to sell to, a sales leader may lock in a motion before it is proven.
• Pricing and packaging are unsettled. Frequent pricing changes make it hard for any leader to build a stable process.
• No one has sold it but the founder. If only the founder can close, consider hiring one or two strong account executives first to prove the motion can transfer.

In these cases, a strong first account executive or a head of sales who is comfortable selling every day may be a better first step. Our account executive recruiting work often starts here.

What profile to look for

Stage experience matters more than logo experience

A leader who ran a large region at a well known software company may be impressive on paper, but they may also be used to marketing support, sales operations, enablement and a recognized brand. Look for someone who has built at a similar stage, ideally taking a team from early revenue to the next level.

They still like to sell

Ask candidates about deals they personally closed in the last year or two. Your first VP of Sales should be comfortable on the front line, not only in the pipeline review.

They can recruit

Their success will depend on the account executives they hire. Ask how they found and hired their best reps, and talk to some of those reps during references.

They fit your buyer

Selling AI and SaaS products to technical buyers is different from selling to line of business buyers. Look for a leader whose experience matches the way your customers evaluate and purchase.

How to run the search

1. Write a scorecard first. List the outcomes you expect in the first 12 months, not just a list of traits.
2. Agree internally on the profile. Founders and board members should agree on player versus manager before you meet candidates.
3. Test for real skills. Ask candidates to walk through a forecast, a comp plan or a hiring plan for your business.
4. Check references deeply. Speak with former managers, peers and people they hired.
5. Sell the opportunity. The best candidates are usually employed and have options. Be clear about the mission, equity and what support they will have.

For more on building out the leadership layer, see our sales leadership recruiting practice and our work with AI companies.

FAQ

Should my first sales leader be a VP of Sales or a Head of Sales?
The title matters less than the scope. Many Series A companies hire a Head of Sales who can grow into a VP role as the team grows. Be clear about the expectations either way.

Should a Series A company hire a CRO?
Usually not yet. A CRO typically oversees sales, customer success and sometimes marketing across a larger organization. Most Series A companies need a hands on sales leader first.

How long does a VP of Sales search take?
It depends on the market, the profile and how quickly your team can make decisions. Starting with a clear scorecard and a committed interview team shortens it.

Can we promote our top account executive instead?
Sometimes. A great rep is not always a great leader, so look for evidence they have coached others, built process and enjoy recruiting.

Talk to Steve

Thinking about your first VP of Sales after Series A? Book a 15 minute hiring call with Steve.