Learn the optimal process to interview and hire your first sales leader. Make sure you know the key traits that you should vet for throughout the interview process.
The default for most startups is founder-led sales, but as the team and company grows, you will eventually need to hire your first sales leader. Hiring a VP of Sales or CRO will depend on which milestones you've hit that are defined by the CEO and the Board. This typically starts at a specific revenue target, pipeline metric, and/or user-counts for a product-led-growth model after you've found some form of product-market fit (PMF).
There are several elements to consider that determine the type of sales leader you would need. We’ll touch more on this in a future post, but there are some common traits every sales leader should have and which you should vet for throughout the interview process.
Here’s the interview process and questions we use at Unusual, working alongside our portfolio companies to ensure a successful sales hire at the seed stage.
Start with some personal questions (learn about them as a person, care about getting to know them): 5-10min
Transition into the career questions (listed below): 15min and/or 60% of the allotted time
End by letting them ask you any/all questions they have + next steps: 10min and/or 20%-30% of the allotted time
This is a big decision and one that’s very personal for both parties, the worst thing either of us can do is oversell the other, so I’m going to be very transparent and just ask that you do the same if that’s ok with you
Take me back to (University, a specific job, etc) and walk me through how you got to where you are now and why you made those moves
When it comes to sales at X, what’s your process?
What’s the most difficult feedback you’ve received and how did it change you/your approach?
Who are the three most influential people in your life? Why?
Who was the best manager you ever had? Why? Worst manager and why?
What’s your current breakdown between inbound/outbound?
Where do you rank currently on the team? If number 1, what are you doing that others aren’t? If not, what are they doing that your not?
Out of the following, which is the most important thing to focus on (only one right answer):
We're looking at a lot of candidates for this role, why are you the best fit for it based on where the company is in its journey?
What deal sizes have you sold to, on average, and range? (If it’s not a similar fit to you, pass. If he/she can’t answer fluidly, pass).
Tell me about the teams you’ve directly managed, and how you built them. (If he/she can’t describe how they built a team — pass).
How big a team do you think we need right now, given what you know? (If he/she can’t answer — right or wrong — pass).
What sales tools have you used and what works for you? What hasn’t worked well? (If they don’t understand sales tools, they aren’t fit to be a VP of Sales).
Who do you know right now that would join you on our sales team? (All good candidates should have a few in mind). Tell me about them, by background, if not name.
How should sales and client success/management work together? (This will ferret out how well he/she understands the true customer lifecycle).
Tell me about deals you’ve lost to competitors. What’s going to be key in our space about winning vs. competitors?
How do you deal with FUD in the marketplace? (This will ferret out if they know how to compete — or not).
Do you work with sales engineers and sales support? If so, what role do they need to play at this stage when capital is finite? (This will ferret out if he/she can play at an early-stage SaaS start-up successfully — and if he knows how to scale once you scale).
What will my revenues look like 120 days after I hire you? (Have him/her explain to you what will happen. There’s no correct answer. But there are many wrong answers).
How should sales and marketing work together at our phase? (This will ferret out if he understands lead generation and how to work a lead funnel. Believe it or not, most candidates don’t understand this unless they were really a VP Sales before).
Walk me through the deal you're most proud of - (Similar to "What deal sizes have you sold to, on average, and range?") - The best reps will walk you through a complex deal with a high price tag, and tell you notable milestones or the adversity they overcame. Strong examples lead to good conversation and naturally highlight the areas in where they spike and areas where they need improvement.
First interview question: "Why are you interested in this role, and why this company?" (Did this person do their research? How much? If they aren't willing to sell themselves or express genuine interest in the interview process, how will they do selling your product?)
How many questions did they ask you?
How did they differentiate themselves from other candidates?
How much research did they do on your company/space coming into the call?
Did they make any excuses, blame others, or bash co-workers during the interview?