Your first sales leader probably shouldn’t be a CRO

You may want someone who has run a hundred-person sales team, presents impressive plans to the Board and knows how to build an international organisation.

But that is probably not the job you have today.‍ 

Your first sales leader needs to be at the coalface. They need to join Discovery calls, progress opportunities, help close deals, listen to call recordings and understand why prospects buy - or don’t.‍

Founder-led sales may already be working. But founders can sell through their authority, product knowledge and ability to make decisions or commitments instantly. An AE cannot simply copy that.

The sales leader’s job is to work out which parts are repeatable:

• Who is the genuine ICP?

• Which messages create interest?

• What does good Discovery look like?

• How should opportunities be qualified?

• Why do deals stall?

• What can another competent seller follow successfully?

You discover this by working on real deals, not by building a Board plan.

The danger of hiring somebody too senior is that they naturally want to build the organisation they previously managed. They hire AEs, add BDRs, purchase technology and introduce forecasting processes.

‍But if the sales motion is not repeatable, additional people simply scale the problem.

 Of course, some CROs remain excellent frontline operators. The title itself is not the issue. The question is whether they genuinely want to do the work required at your stage.

So, before hiring, ask:

• When did you last personally own and close a deal?

• How have you turned founder-led selling into a process other people could follow?

• What would you personally do during your first 30 days?

• What evidence would you need before hiring additional sellers?

• Which calls and opportunities would you expect to join?

Be wary if the answers focus immediately on organisational design, recruitment, technology and Board reporting.‍ 

Look for someone who wants to spend their first few months working alongside the founder and sellers: listening to calls, testing messaging, closing opportunities and documenting what works.

Agree the outputs before they join. Within three months, you should expect clearer qualification, a more reliable sales process, better coaching, improved forecasting and evidence that somebody other than the founder can close.

Your first sales leader must produce revenue. More importantly, they must turn every win and loss into a process that other people can follow.