In the early days of SaaStr, we wrote a bunch of posts that were controversial at the time, but later, most sales leaders eventually agreed with. That you know early. That you know even in 1 sales cycle if a VP of Sales is going to work out.

Yet, in some ways, this breaks down a bit in tougher times. If sales cycles are long and getting even longer, how can you know if it’s your VP of Sales … or just macro issues?  How do you know if it’s “the downturn” — or it’s you?

 Let’s take a look at our classic checklist and see which criteria apply in a downturn in your core business — and which maybe aren’t fair to use to judge your new VP of Sales. Our classic 10-point checklist of Warning Signs. That she or he just isn’t going to work out … at your start-up. Maybe at a different one, at a different time, or stage, or subject matter they might be successful. But not at your start-up:
  • The Blame Game – Down.. As soon as you hear a VP of Sales start to blame her/his own reports for missing a number, it’s over.  These are her/his own reports, after all. When a VP of Sales has lost confidence in his ability to hit a number, it’s always easy to blame someone on their team. But a great VP of Sales never does, at least not more than once or twice. They just … take care of their mishires. They blame themselves first. In fact, they don’t even take that much blame. They just come up with a new plan that is realistic, that pushes the team, and that makes sense.
  • The Blame Game – Product (too much). A little of this is OK, and fair. The product is always feature-poor and missing critical needs for customers. But that was also true before you hired the VP of Sales …
  • The Blame Game – Competition. Yes, competition is brutal. But again, it was right before he started and before a global pandemic, too. A great VP of Sales gets better at competing over time. Not worse. A great VP of Sales takes advantage of fear in the competition, and of complacency, and pounces.
  • The Blame Game – More Time. You can’t expect results overnight. But you can expect some improvement in 1 sales cycle. More on that here. More time does not cure sales woes. But … sales cycles are often way up, and close rates way down. You still will know in 1 sales cycle if she or he is going to work out. It’s just, that’s 1 sales cycle may be longer, and different.
  • An (often big) drop in quota attainment.  Quota attainment should go up when you hire a great VP of Sales. But with a mediocre one, or really, a VP of Sales that is just a bad fit … you often see quota attainment plummet. Quickly. Everyone’s quota attainment may be down now. But instead, look at your top performers. If they are sort of checking out right now … that’s a sign you hire the wrong VP of Sales.
  • Top reps leaving. The best VPs of Sales know how to keep their winners. They never let them leave, in fact. If you see winners leaving, you have the wrong VP of Sales. Period. This may sound obvious … yet, this is very common to see.  Don’t accept excuses here. This is as clear a sign as you are going to get.
  • “We’ll make it up next quarter.” Sometimes this is true. There are always better and worse quarters. But a great VP of Sales never, ever simply dismisses a bad quarter by saying they’ll make it up next quarter. Instead, she says, “This was a tough quarter. Here’s what we screwed up: ____, ____ and _____. It’s mostly fixed now. So next quarter, ….” No great VP of Sales should be saying it will be easy to make-up a big gap now. Or in many cases, that it is even possible. Instead, by now, they should have a new plan. A real plan.
  • A crazy plan that doesn’t really make sense or tie to data. Related to the prior point. A bold plan can be good. But no, you can’t just magically quadruple sales in Q4 when you were only growing 20% in Q1. A crazy ramp is an excuse in disguise and waiting. It’s kicking the can on having to explain that you don’t really know how to improve sales.
  • A drop in revenue retention. A strong VP of Sales in a start-up is focused on the ARR goal, not just new bookings. She’ll know some of her highest leverage in hitting the ARR plan for the year is increasing upsell, increasing net revenue retention, and decreasing churn. Even if Customer Success isn’t remotely part of her nominal job description, she’ll still want to own enough of it to see flat or improved revenue retention. Of course she will. Her job is just that much harder if retention declines. A great VP of Sales still cares as much about the ARR goal as bookings in SaaS. You’ll see the great ones figuring out now what they can do to retain their customers, especially the top customers — maybe even more so.
  • Not understanding the business and/or key metrics. I see this too often. 🙁 A VP of Sales that doesn’t know how the company defines an MQL. That isn’t sure how many leads sales got last month. That isn’t clear on how a new key feature works. That doesn’t know the status of a key Top 10 deal (this one is way too common).

And finally:

  • Fear. Sales is hard. It’s hard to hear 50 “Nos”. It’s hard to lose a big deal to a competitor after you put months in a deal. It’s hard to be judged quantitatively every month and quarter. It’s hard to always have to do better. It’s just hard. And sometimes, it’s simply too hard. When you see fear in the eyes of your VP of Sales, it’s over. It’s even harder now. There are more reasons to be scared. And yet, somehow, the best VPs of Sales don’t let fear seep in. In fact, they are even better leaders now than they were 60 days ago.

So a couple of the top 10 excuses, the top 10 signs a VP of Sales just won’t work out, don’t apply as much on all levels when your business is under stress. Sales cycles are lengthening for many of us.  But most hold, tougher times or better times.

The best sales leaders are still outperforming their peers on a relative basis. I hired my real VP of Sales in a downturn. He doubled sales in 90 days. You can’t expect that. But you can expect improvement at least at a qualitative level today. And you can look for the signs they may just be making things worse in these somewhat confusing times.

Related Posts

Pin It on Pinterest

Share This