Assessing the Substructure of SaaS Startups

10 questions to ask founders in an interview

It’s tough for the first VP of Sales to know whether they’re joining a future rocket ship or a zombie startup.

Many would argue that the outcome of the startup is inextricably linked to this hire itself. However, in reality, the substructure is already built or at least formed to some extent before, and that sub-structure is going to have a huge impact on the outcome of your success as VP of Sales.

In an interview as the first VP of Sales, it’s on you to uncover what that sub-structure is made of.

To do that you need to take the founder back to the early stages of when the startup was formed, to their very first customers, the lessons learned and the actions taken as a result of those lessons.

Founders typically like to tell their personal back-story and how the startup came about but very few when interviewing a VP of Sales get into the detail about their inaugural customers. But for you as the VP of Sales, this is where the gold lies. You should uncover the detail in your earliest conversation with a founder.

Consider this framing:

”In my experience, the foundation of the future sales org is built very early in a startup’s evolution, by you the founder. I’d love to get into some detail about your earliest customers so that I fully understand the go-to-market heritage of the company”

Suggest you’d love to focus on the beta customers of the startup, and have them walk you through examples of those customers, hopefully, they’ll name at least 10 or so.

Once you’re there, here are 10 questions you should ask about those inaugural customers, reasons why they are important questions, and what to look out for in the dialogue that follows.

---

1. Why did you choose these companies as beta customers?

Why ask: There’s a world of companies to choose from, this will give you insight into their perceived ICP and their upper funnel approach.

What to look for: What you want to see is a systematic approach to targeting companies that was successful in garnering both initial discussion and an agreement to be beta customers.

What you don’t want to hear is that they exclusively called on friends to do them favours to be their beta customers!

---

2. How did you successfully book meetings with them?

Why ask: The outbound motion is critical to understand, it’s highly likely your job is going to be scaling that very motion!

What to look for: Look for something that is documented that you believe you can improve. This is the motion that will likely make or break you. Once again, ensure it’s not a friend’s network because you obviously can’t scale the founder of their network, not sustainably anyway!

---