I’ve seen a lot of new VPs of sales fail lately when they start. Is it their fault? The CEOs? The VCs? In the end, it doesn’t really matter.
One thing I do know is that many mistakes can be avoided.
You might laugh at some of them, but here are the 10 most common mistakes I’ve seen new VPs of Sales make in their first week on the job. The ones I’ve seen recently:
#1. Not knowing the product thoroughly before starting
Many founders won’t push this point. They’ll love it when a VP of Sales talks about process (a lot of process), about team building, and about how to make things better. But many VPs of Sales start way, way back when they think they can learn the product on the fly.
#2 Don’t start… before you start
VPs: Start the week before you start. Start using email and Slack. Listen to more calls. Silently add recipients to copy lists. Watch recordings of team calls. You don’t have to literally be on Zoom before you start. But on day one, don’t spend the entire time setting up G Suite and figuring out the tech stack. The best start is before you start. I recently saw a VP of sales show up at 10am on their first day, without even logging into email first. No chance.
#3. Insist on having it done your way
This is a tough one. Of course, as a sales leader, you have your way of selling, a way of managing, a set of systems and processes that you were taught and grew up with. And the startup you join almost certainly has different Too often I hear a new VP of Sales say something like, “We’re not doing it this way anymore.” Often on day one. Look, it’s okay to think that, and it’s okay to quickly level up the team. But first, find the good in what’s working. If you’re joining something that’s already growing quickly, slow down and learn what’s working first. Before you change anything.
#4. Not having anyone to join them
This is an original SaaStr post, point, and theme, but as true today as ever. It’s nearly impossible to hit the ground running as a new VP of Sales if you don’t have a few reps you trust and know are strong and willing to join you quickly. Not always on day one, but quickly.
#5 Not asking enough good questions and not being curious enough
Too many VP of Sales candidates today try to (1) turn every interview into a founder interview and (2) talk about the process. I see a lot of candidates basically following this playbook when interviewing with CEOs and board members: “Tell me more about the company.” They’re vague. And then they show a PowerPoint deck they’ve used before about how they scale hiring. From 8 reps to 16 to 64, territories, etc. The process slides always look amazing and sound like what you need. But it’s not even remotely what you need. You need a great, hands-on executive with a curious mind. Who really wants to learn why and how customers buy, and who’s already done a lot of homework in the space.
#6. Don’t start outbounding in week 1. Or at least with some kind of outreach
Okay, some may disagree with me on some of this, but the best VPs of Sales do some outbound in their first week. It may not be a structured program, but at least they start communicating with some people in your network. Some people from the industry, etc. They begin to approach some potential prospects that are not yet in the pipeline.
#7. Not being able to demonstrate the product themselves
You have to get there in week 1. Week 1. Or you probably never will. There’s nothing wrong with having sales engineers, solution architects, and all that in some sales motions. But if the VP of Sales never learns how to actually demo the product in week 1, they almost never will. How do you teach if you can’t do it yourself? These VPs of Sales again end up being all about the process. But they can rarely be allies to the customer. Because they don’t know. It also shows that you can meet the first criteria/point above.
#8. Not understanding existing GTM proposals
I see a lot of VPs of Sales who, for example, have only sold direct and don’t understand a sales process that also has a large partnership or channel component. 40-50% of Shopify, HubSpot, etc. revenue comes from agencies and partners. Many VPs of Sales don’t really understand how all of this works before they get started.
#9. Wanting to start a bigger business right away
There’s no doubt that most SaaS companies will turn to a more sophisticated market at some point. It’s an important issue for publicly traded SaaS companies today, even those that have historically focused on SMBs like Monday and HubSpot and AsanaBut it’s not always the right idea in week 1. If 90% of your revenue comes from SMBs, it might be better to learn that move first.
#10. Not truly understanding the ecosystem in which it operates
A variation on the above point. But in many cases, you have to go deep into the ecosystem to succeed. If you’re a Zendesk partner, you should be there by week 1. No… learning how Zendesk actually works by day 100. Again, too many VPs of Sales think they can wing it.
Look, it’s hard work :). There’s a lot to learn, and very quickly. At the very least, learn as much as you can. before You start. Too many people wait until they start learning, and that is often too late.
Trust me.
And a little more here:
The 10 Most Common Mistakes I See in the Sales VP Hiring Process
