Many tech companies in the pre-$50M stage churn through sales leaders regularly. Some of the reasons are macro, others are pinpointable at the individual company level. Each case is a bit different, so here are the most common reasons it’s tough to get right.
You may think the problem is one thing, but it’s actually another. In some cases, the problem sits at the VP level. In others, it’s the CRO. It can be hard to tell where it actually lives.
One of our clients isn’t hitting their numbers. They have several VPs of Sales, one for each market segment: SMB, mid-market, and enterprise. They’ve churned through three CROs in the last two years.
With each change, existing reps have come and gone, and comp plans have been rebuilt about every 12 months. New reps, sales enablement, and pre-sales all got refreshed with each new leader too. At this point, so much has changed that pinpointing the actual problem gets genuinely hard.
They work in some situations and not in others. Many haven’t spent time in the seat selling in years. That can be good or bad, but it makes them even harder to assess. I’ve seen exceptional sales leaders who haven’t personally sold in over a decade. But I haven’t seen a good one who spent three years or less face-to-face with customers before moving into leadership.
The opposite is just as true. I’ve seen strong individual sellers move into leadership and end up hating the job. They get frustrated with their reps, and the only version of the role they succeed in is what we call the “sales leader as a super rep,” which isn’t sales leadership at all.
Sometimes what you want the sales leader to do is out of scope for the role. It’s like hiring a heart surgeon who’ll also be your kid’s pediatrician. It’s understandable why you’d want that, but it won’t work.
We had a client who wanted to hire a Head of Sales to eventually take over selling for him, the CEO and founder. He wanted this person to run all the demos, close the deals, and then build and hire a team down the line. That profile can work if you promote a rep into a Head of Sales role over time, and even then it’s a maybe. But someone who’s already built teams from scratch to $10M isn’t going to sign up to be your new solo top salesperson.
Don’t let any of this talk you into thinking sales leadership hiring is a crapshoot. It isn’t. Some of the best software companies get this right consistently. If you’re hiring a sales leader, working with a specialist recruiter can be the difference between getting it right and burning through cash.
