We just hired a VP of Sales for our Series A startup. Here are 4 important lessons.

We recently wrapped up a thorough, multi-month process to find our first VP of Sales. This ended with Cris Mendes accepting our offer and starting this week (hallelujah!).

Here's a little about us: We sell an enterprise listening platform to Sales, CS and RevOps leaders. We've been doing founder-led sales for the last 18 months, with the recent help of promoting a couple SDRs to assist in deal admin and working SMB deals on their own. Its been immensely valuable to talk to prospects and customers all day long.

So why did we hire a VP of Sales?

Running sales is a full time job. And sales is just one very important part of building a business. After raising our Series A this summer, our trusted investors at FirstMark and Stage 2 Capital felt strongly that bringing in a sales leader to own sales end-to-end (with us still involved) would allow us to focus on other parts of the business, like marketing and product.

We're in a highly competitive space, and both brand building and product strategy will be critical focus areas for us this next year. I share that because I can't tell you the number of founders and sales advisors who said, whyyyyyy do you need a VP of Sales right now. That's why!

Here's what I learned about hiring for a critical role like this as an early stage company:

1. Go deep in making sure you have alignment between founders and investors before you're too far in the process.

This might seem like a "no duh" thing, but as I quickly learned, there's a lot of nuance in discovering what people actually want in a candidate.

In our case, we were 3 founders and 3 investors making the decision. We thought we had alignment as we kicked things off. We talked through the title and level (Director of Sales vs. VP of Sales); the experience they should have (player-coach w/ a couple years of leadership exp. vs. multi-time VP); the industry they were coming from; comp; location, etc etc etc.

And yet...once we were in the interview process, it became clear that we had to get into the nitty gritty expectations that each of us had and talk through it over many conversations. When you're managing multiple stakeholder opinions, this becomes even more important.

If I were to do it again, I'd run a longer up-front internal process to make sure we were fully aligned on the must-haves, and not spend any time interviewing people who didn't fit the criteria for everyone involved. I'd capture all of the expectations in a checklist, but also interview each person to ask these two important questions:

What are 3 things he or she must have to be a fit for us?

Are there any absolute deal-breakers for moving forward with a potential candidate?

2. Build a solid strategy upfront for finding candidates. Then prepare for it to get noisyyyyyyy

We found possible candidates a variety of ways; inbound intros, the Stage 2 network (thanks, Mandy and Andi!), Casey Marx, FirstMarks' recruiter (who was awesome and ultimately sourced Cris), and through 2 external recruiters who just happened to reach out to me as we were kicking off the process.

At first, it felt like the right move to have many folks coming in from different places. Better to talk to lots of people to see what we want, right?

But before I knew it, my inbox was blowing up, and it was overwhelming to manage all the different candidates, the stage they were in with the interview process, keep our internal stakeholders updated on the process, as well as stay engaged with the recruiters themselves.

Next time, I'll make sure that I have lesson #1 covered incredibly well (i.e. alignment on expectations) and then engage ONE recruiter/candidate source at a time. I also will do a much better job vetting outside recruiters. Everyone says they won't spam your inbox with candidates and then...they do (can't really fault them, this is the job).

3. Have LIVE conversations with all reference checks. DO NOT PASS GO WITHOUT THIS STEP.

I used to think that reference checks were just a quick "last step in the process" sort of thing. Now I see that, for critical hires especially, this is just as important as the interview itself.

It's not enough to just email someone and get a written response on how a potential candidate did in a past role. You have to actually get on the phone with MULTIPLE references and talk about him or her live.

We learned that we needed to get references of people who reported to the person, who worked alongside the person, and who managed the person. This is the only way to get a good 360 view.

Founders, please don't skip out on this and if it takes you an extra week to have those conversations, so be it.

4. Index heavily on culture and founder-fit (once you make sure they can do the job)

Whether we want to admit it or not, executive hires are joining our world; not the other way around. As founders, our company is ultimately a reflection of us, and you need to make sure the person signing up for the role is aligned with what we care about.

We made sure that we had multiple conversations around how we work, what our expectations are and what we believe in. But we didn't hesitate to circle back with candidates, especially as we got further along in the process, to double-click on certain items and to make sure we had talked honestly and openly about what we work, what we believe in, and what our expectations are.

One of our values and shared personal traits between the founders is a high degree of transparency, so this was actually one of the easier things for us to put into the process. But I want to highlight just how critical it is to go with some gut-level instinct and make sure you're going to vibe with someone you'll soon be entrusting a critical part of the business to.

And now - we roll :)

We all breathed a sign of relief when we made the offer to Cris and he accepted. But the best part is feeling like we covered as many of the bases as possible before jumping into this together.

Signing up for early stage startup life is a journey in risk and commitment on both sides, and you want to make sure you've done all you can to identify the gaps before you say yes (hmmm, sounds a bit like a marriage...turns out, there are parallels!).

Welcome aboard Cris M. ! Super excited to see what 2025 brings.