A Lot of Great Sales Leaders Just Aren’t Great at Selling Anymore

So this isn’t a sub-tweet, or sub-post. I’m not talking about any close friends in sales here. But — there are a ton of folks I know that used to be great in sales. But not anymore.

The other day someone who used to be an A+ sales leader emailed me about a position I’d introduced to him as a super hot start-up. The email to me was:

“What do they do again?”

I mean laugh if you want. But he used to be great. Maybe not epic, but really a sales leader I looked up to. Almost too smart for his own good, but great. I made intros and connections and put him on stage.

But it doesn’t matter why. He’s not that today. And you just might want to hire him.

Because his LinkedIn looks great, and he knows process. And the talk.

But he just isn’t a great seller anymore. He’s done selling, and probably, being curious. When you hire the perfect resume, make sure they still are, too. If he doesn’t even exactly know what an A+ company I introduced him to does … he’s just looking for a soft landing place.

Your startup almost certainly isn’t a soft-landing place. No matter how much you’ve raised.

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So recently we did a deep dive with Henry Schuck, founder CEO of ZoomInfo, on AI in Sales and so much more.

We’ve done a series of incredible highly operational conversations with Henry over the years, so I turned the convo around to ask him about a topic I still wonder about and struggle:

How do you continually recruit VPs and C-level execs … forever? Again and again?

I find that the hardest part of all of this. To constantly be recruiting the best.  Not just hear and there. But constantly. And … again and again. Because if you go long, many of the best will eventually leave.

I’m going to paraphrase his answer, but I 100% agree it’s the right one:

Do it all, do all the interviews, etc. But make sure if nothing else, you hire One Senior Exec a Quarter. Force yourself to do that, focus there, and prioritize on the most critical VP/SVP exec for that quarter.

The #1 reason I see sales execs struggling today in new roles: they are convinced their playbook is better. And refuse to run the one that is already working.

They are convinced they know better. That the founders are wrong, or whomever is running things is either wrong, or to be ignored. “That’s not the way I do things” or some variant is something I often hear these days.

It’s not that they don’t sometimes have a point. Every start-up is deeply flawed on many levels :). And yet, the successful ones still find a way. And you have to run their playbook, 9 times out of 10, to succeed in sales. Not yours.

And so I see these seasoned sales execs blow up 30, 60, 90 days in when they get frustrated when they are pushed to run a new playbook.

I can’t imagine going to Salesforce or Oracle and joining as a sales exec and insisting on running your own playbook. But I see it all the time at start-ups.

It’s complicated. You are being hired in part for your experience. But maybe not in the way you think.

Add on to what’s working, don’t accidentally (or intentionally) do an end-run around it.

Or you may end up bouncing out of a role that could have been great at.

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We all sort of know how to fire an underperforming employee. Sort of. You let them know kindly, with care.  And move on.

But how do you fire a good >client<? One that has been paying regularly, for an extended time? That counts on you?

It happens. The reality is for service providers, you only have so many slots. Some clients are just too demanding. It’s easier to have clients that are less demanding. And sometimes if you do well, you just plain end up with too many clients. And you have to let some go.

The ones that never pay, that’s easy. The ones where you don’t do all that much for, you just wind it down.

But what about the clients that depend on you? I’ve had a few of these conversations over the years. At law firms, accounting firms, and marketing agencies where after a few years, they want a less demanding client than me and/or SaaStr.

I had an accounting firm I’d used for years not want to work with us anymore for example, when managing our taxes got a lot more complicated. And a law firm not want to work with us when we decided not to get as big as A16Z. Etc.

All I can tell you is I just don’t see agencies think about this much at all from the client’s perspective.

The real work starts.

Having been through 4 acquisitions in different forms (founder, exec, etc), it’s a lot like a venture capital investment. Usually, there isn’t actually a ton of time to really get to know each other first. Not really.

A ton of time is invested negotiating price, and then way, way too much time on inconsequential legal terms, and then … it closes. Oftentimes, very little true operational planning is done on what to do after.

It will all seem super-important to you, but from the acquirer’s perspective, they also have a core business to run, and each of the VPs already have a lot to do. They’ll only go so deep in figuring things all out before the deal closes.

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