Before You Hire Your Next Sales Leader, Answer These Five Questions

Over the past month, I've spent time reading VP of Sales job postings, particularly for companies hiring their first senior sales leader as they transition from founder- or CEO-led sales.

The language is remarkably consistent. Companies are looking for a strategic, hands-on leader who can build the go-to-market strategy, create the sales process, hire and manage the team, build pipeline, establish forecasting discipline, and often continue selling along the way.

Those are all reasonable things for a growing company to need. But before asking one person to take responsibility for all of them, there is another question worth asking:

Is the organization ready for the sales leader it is about to hire?

Here are five questions I would answer first.

1. Can we clearly articulate why customers should buy from us?

A strong salesperson can communicate value. But they shouldn't have to invent the company's value proposition after they arrive.

2. Can we clearly define our ideal customer?

An ICP should be specific enough to guide sales decisions. If it describes a broad swath of the market, there may still be important work to do before asking someone to scale sales.

3. Are our sales goals grounded in the realities of the business?

Growth goals should be ambitious. But leadership should understand the assumptions behind the number before holding a new sales leader accountable for delivering it.

4. Do we have evidence that our sales model is repeatable?

Founder-led sales can be very successful. That doesn't necessarily mean the model can be handed to someone else and repeated.

5. Are our expectations for the role—and the timeline—realistic?

Building a sales system, leading a team, and selling are distinct responsibilities. When one person is expected to do all three, expectations for what they will accomplish and how quickly should reflect that.

Hiring a strong sales leader can be an important step in a company's growth.

But hiring the right person and putting that person into a system that is ready to support them are two different things.

Before beginning the search, understand what is already in place, what still needs to be built, and what you're actually asking the new leader to accomplish.

The Ashley King Advisory Perspective

Before you change the people, examine the system.

And before you add the people, make sure the system is ready for them.