Why the star hire fails, who actually works, and how to build sales as a machine rather than a set of pitches.

Founders hire salespeople the way they hire everyone else: find the most impressive person available and hope. Sales is the one function where that instinct backfires hardest.

We asked Hlayisani Capital co-founder and partner Brett Commaille, who has spent around 15 years watching founders make this hire, how to get it right…

Brett’s starting point is uncomfortable: the majority of sales hires he’s seen have been wrong. The reason is a specific trap, and it’s the exact person a founder is most tempted to hire.

“Salespeople are very good at selling themselves, and sometimes bad at selling the product.”

The seductive hire is the one with the enormous logo behind them: this person worked at Oracle, ran billion-rand accounts. The problem, as Brett puts it, is that Oracle was selling itself and the person was merely the delivery mechanism. Take them out of that machine and the deals stop coming, because they were never the reason the deals closed. The brand did the selling.

This isn’t a small mistake to unwind. Brett’s maths: six months to hire, six months to ramp, six months to fail, so roughly 18 months gone and you’re further behind than when you started. That timeline is why getting the profile right matters more than moving fast, because the fast wrong hire is the slowest possible route to a working sales function.

What works is the opposite of the trophy CV: mid-market sellers with no big brand behind them, dogged, teachable, and unwilling to let go. Not amazing logos, a great attitude. Going too junior is its own failure, though, because you can’t put someone green in front of a serious buyer like Capitec. The target is someone hungry and coachable enough to learn your product, senior enough to hold the room.

The deeper point is that the goal isn’t a person; it’s a system. Fill the top of the pipeline, learn what works, kill what doesn’t, get a repeatable result, then invest behind it and add reps. Bad salespeople improvise every pitch, which Brett calls the dark arts, so nobody can learn from them. Good sales is documented and repeatable: US startups running 500 reps off a script can confidently throw $100m at a process that reliably returns $250m. Check every stage, from interest to contracting to delivery, constantly, because sales works when it’s a machine.

The last one is a mindset check on the founder, not the hire. A CEO uncomfortable with the salesperson being the top earner is a red flag, because a salesperson seldom has equity and everything in their world is commission. Brett’s framing: if you have ten salespeople earning more than you, you are winning. Restricting a great salesperson’s commission is how you cap the exact person you hired to grow the business.

Get this hire right, and you don’t just add a seller; you start building the machine that lets you add ten more with confidence. Get it wrong, and you lose the best part of two years and land back where you began, more convinced than ever that sales is the problem.

Brett’s full fireside from Founder Collab Live is available to members inside the Founder Collab, where he goes further than we could cover here:

You’ll also get access to 40+ masterclasses from SA founders and operators on sales, fundraising, UX, paid media and more inside The Founder Collab.

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