The Double Stretch Hire

I was chatting with a client CEO recently who admitted he was struggling to stay focused in the CEO seat. Sales needed his constant attention (which quite honestly he was fine with) but so did everything else.

That conversation reminded me of a recent SaaStr article on “stretch hires.” It’s a topic every early-stage CEO wrestles with: hire the proven VP with the perfect resume, or take a bet on a stretch candidate who hasn’t actually “done it” yet?

What struck me from the article was the danger of the double-stretch hire, that stellar individual contributor who wants to leapfrog into the VP role, or the Director who insists she’s ready for C-level.

Here’s my take:

1. Start narrow, sequence later.
Stretch hires succeed when they begin with an intentionally tight, almost maniacal focus. Maybe it’s inside sales only, or just demand gen, or just onboarding. Keep the lane narrow, let them prove themselves, and then expand scope as the months progress and performance is proven. Sequencing like this gives them room to grow without drowning them.

2. Coaching isn’t optional.
Even the best hires enter with insecurities and blind spots. They know they haven’t done it before, so dropping them in and expecting magic is a recipe for disaster: lower results, employee churn, customer churn. A mentor on Day 1 can make the difference between confidence and collapse. I personally grew into my leadership role the most when I had an outside coach.

3. Role clarity is non-negotiable.
As scope expands, each new responsibility addition has to be crystal clear: scope, success criteria, and ownership and accountability. If not, people cherry-pick the parts of the role they like, neglect the rest, and results are mixed. Fuzzy roles at the leadership level almost always cascade into fuzzy execution, and then revenue and retention suffer.

So yes, stretch hires can work, but only when they’re supported with:
🔹 Narrow early scope, sequenced deliberately;
🔹 Day-1 coaching and mentorship;
🔹 Ironclad role clarity with defined success criteria.

Without those, you’ll likely end up with a failed promotion and the CEO (again) wearing too many hats.

If you’re going to bet on stretch hires, make sure you’re also betting on focus, coaching, and clarity. That’s how you boost retention, both talent and your customers.