The Double-Stretch Hire Rarely Works Out

Over the past years at SaaStr, we’ve summarized a lot of VP-level hiring decisions down to one strategic choice: do you pick a Stretch VP, one that hasn’t quite done it before, a Director of Sales to be your VP of Sales, etc. …. or do you pick someone that has the Perfect LinkedIn, and has seemingly done it all? 

The choice in reality is often not a choice, but rather an illusion. Because the perfect candidate, even if she really exists, isn’t going to join your start-up. Not until you are Uipath, or Intercom, or Algolia, or whatever. So that perfect LinkedIn, that seemingly perfect VP experience … well that candidate is usually either a wash-out, or someone that never really did it.

So for 90% of you, a Stretch VP is better than someone that is more seasoned, but hasn't really done it. Not at your stage, etc.

A few classic posts on that “choice” here. They are pretty good and each worth a read:

• If You are Going to Hire a Stretch VP — Do It Early
• The Benefits of Hiring a Stretch VP — And The Risks
• How to Succeed as a First Time VP of Sales

But now we are getting into Year 12 of the SaaS/Cloud bull run, and the choice has evolved. Everything is overheated, even during these crazy Shelter+ times.  So the question many founders are now faced with is not just to make a Stretch VP Hire … but whether to risk a Double Stretch Hire. A VP candidate stretching 2+ levels up the experience ladder. Typical examples are:

• A truly top individual sales exec with no true management experience wanting to be a VP of Sales. This is a risk so many of you take.
• A director of marketing experienced in one area (e.g., corporate marketing or growth hacking) insisting on being your CMO.
• A customer success leader that was good at upsells — which is sort of, but not really, sales — that insists on being your VP of Sales.
• A director of sales with some team management experience that wants to be your CRO, and own the entire number, including renewals, success, everything.
• A top SDR that wants to skip the AE part and be your Director of Sales.
• Etc. etc. etc.

You can feel like you are in a tough spot when one of these candidates seem super-talented and pushes you hard for the title, and more importantly, the role. It’s so hard to find anyone great, and these days, competition for talent is the fiercest of all time. The simplest risk to take is often to just hire a “double-stretch” and hope for the best.

I wish I could tell you I’ve seen this work out. But really, I haven’t — with just a few exceptions.  Those exceptions are where you have time. If you hire a double-stretch candidate super early, e.g. at 10 or 20 customers … there is time. A double-stretch “business leader” can have 18-24 months to evolve into your VP of Sales, if she joins on Day 30. The same with a double-stretch marketing leader.  Time helps them grow 2 steps up the management ladder.

But outside of very early-stage start-ups, or relatively slowly growing start-ups, there’s rarely time. You’ll hit a wall in 6 months when their first hires don’t work out, or they struggle to manage areas they have no experience in. So the general rule of if you are going to stretch, then stretch early — doubly applies for double stretches. Maybe try a super-stretch in Year 1 of revenue, for the company as a whole or for a new product line. But after that, it’s tough.

OK besides a blanket Don’t Ever Do Double Stretches Except in Year One, what’s another idea, SaaStr? One other.  Start with the Paypal-style of a “barrel” role. Most of us try to make these stretch and super-stretch hires the “Head of” something as a hack to bridge an experience gap, and that’s OK, but it doesn’t really solve the fundamental issue. Which is that there will be too much pressure on them to deliver too quickly at a level that they simply can’t.

So instead, maybe get this Double Stretch hire to first be a Director of One Clear Thing (e.g., Inside Sales, Demand Gen, Customer Success, Outbound) At First — and tell them every 90 days, they can add one more area of ownership — if they are ready. Every 90 days for the first year, and maybe even always.  This is better than an amorphous “we’ll promote you to VP when you are ready”, which won’t make any hyper-ambitious prospect happy. Instead, crisply define the ownership for the First 90 Days. And then add on to it on Day 91. That’s quick, and soon, and you can even force-rank on Day 0 what else they’d potentially own on Day 91 — provided the first 90 Days go according to schedule.

This also gives a talented double-stretch candidate a chance to walk it back at Day 90, if she’s indeed truly great … but not really ready to double-stretch. At least not yet. Double stretches tend to implode when they realize they can’t handle everything that’s been thrown at them. But if you let them wait to add to their plate until Day 91, sometimes they can just keep on plugging away in the zone where they have the most success and experience.

And finally, be it Stretch or Double-Stretch: help get them a mentor on Day 1.  Give them budget (equity and cash) to find one themselves.  More on that here. And even better, go help them find one. Even the best stretches can start off feeling a bit .. insecure. And not sure who to ask for help, when they are dropped into a position where they are supposed to have the answers. Get them a mentor VP on Day 1 who they can talk to. This is almost always the best investment you can make to help.

This quick snippet is awesome on almost all these points: