December 1, 2022

How Does A Startup’s CEO Handle Customers? VP Sales Candidates Want to Know


Bob Berry

In past articles on this website, we’ve interviewed Sales VPs at startups, and asked them what they look for in a CEO.  We hope you’ve found that valuable, but this time we take a different tack.  Rather than asking one single Sales VP a lot of different questions, let’s ask several sales VPs the same question.  For this article, the question we’ll address is:  

What customer relationship skills do you look for in your CEO?

The answers we got were enlightening, with the best answers falling into a few key areas, including:  

Does the CEO have empathy for the customer?  

One highly successful serial Sales VP told us, “Being passionate about solving a problem is not the same thing as having empathy for the people who have that problem.  The best CEOs are passionate about the product they’ve built, and the company they’ve built around that product, but that can be a two-edged sword.  They may find it hard to look beyond the technical and applications issues and really understand the customer’s psyche.” Another VP we interviewed put it another way: “I want my CEO to understand – and respect – the reasons why the prospect might not want to buy.  That’s really the only way we can address those concerns head-on, and get the sale closed.”  

What is the CEO like in front of a customer?  

Many Sales VPs truly appreciate the fact that the sales team and the CEO play very different, but equally critical, roles in the sales process.  One Sales VP recollected, “I was blessed to be the VP of Sales, walking into Fortune 100 companies, and I had the pleasure of selling to those types of accounts through the years. But when I walk in their door, I’m the VP of Sales.  I don't run the company, I run a part of the company, and I don't run the part of the company that builds the product. You need to have a CEO that has the acumen to be a great evangelist for the company, as well as for the product from a senior leadership perspective. Oh, and who doesn't embarrass me in front of the CEO who happens to be a potential customer.”

That part about not “embarrassing” can be critical.  “Sometimes I’m not sure which is worse: a CEO who tries to match wits with the customer and tell him why he’s wrong to want what he wants, or a CEO who comes in at the end of a quarter or a year and completely caves in to the customer’s wishes, undoing a whole lot of work by me and the sales team to construct a business deal that makes sense for everyone,” said the VP of Global sales for a payment transaction security software company.  He went on to say, “Full transparency and having the same agenda are paramount. Even if there's violent disagreement at some point, ultimately you will have to merge and move forward, and you just have to trust that person.  You can't go into your job every day, throwing your entire life at this, thinking they have a hidden agenda, or you don't trust them, or they feel that you can't scale as the organization scales.

Can the CEO learn from customers?  

When asked why so many startups fail, one of our friends said, “I’d call it a lack of responsive leadership. 90% of startups fail, in my opinion, because of a founding team that builds something, but then the reality hits when they go to market, and they learn that even though they built this incredible thing the market isn't quite there yet. But the market is giving you clues and feedback on what to do, how to adjust the technology to market demands. And I think that 90% of startups fail because they don't listen to that market feedback. What they end up doing is they blame the sales organization, fire the leader, rinse, repeat, and then ultimately, just collapse.”  

So if you’re a startup CEO out recruiting for your next Sales VP, these are some things on the minds of those prospective hires, whether they tell you that or not.  How do you measure up?