Hiring Sales#

We’re relaunching our enterprise sales effort after improving product-market fit. However, it’s an interesting challenge finding just the right person. This post goes into a bit of our history, what we’re looking for in an early sales hire, and my experience engaging with this process.

This post may interest you if …

  1. You’re interviewing with me and I’ve pointed you to this post

  2. You’re curious about startups generally

  3. You want to recommend someone in your network (please do!)


A couple years ago we had a sales team, but our product was bad and so the sales team was premature. We fired them (and a bunch of other people) and focused on making a delightful product.

Then, because we didn’t have a sales team we focused on making a product that a user could on-board, use, and pay for all without talking to us. Surprisingly, this worked, and today we have a nice machine that generates happy champions within small teams that pay low thousands of dollars per month (but rarely more).

These people pay us money, but not that much. We’ve been encouraged by two recent learnings:

  1. A little bit of customer support as they onboard greatly accelerates consumption

  2. After talking to customers, we realize that there are often much larger opportunities just behind the initial team that lands with us.

Given this, we’re hiring a sales team again. This should be a fun opportunity for early-stage-oriented sales folks because …

  1. We have a solid pipeline of inbound leads.

    Our product mints new champions regularly.

  2. Our current sales numbers suck, mostly because we haven’t done anything.

    It’s a great opportunity for someone to say “I was the first salesperson on the ground and took them from $0 to $N million in two years” which is a great way for someone to graduate from AE/SE to VP of Sales in their next position (or this one) and maximize lifetime income.

Team Composition#

Ideally we want people who have three skills:

  1. Know how to sell

    Know how to empower champions, navigate an org chart, find economic buyers, identify pain and goals, speak to that pain and those goals, negotiate with precurement and legal, etc..

  2. Know our space (data infrastructure, open source, Python)

    Familiar with Python/Spark/Cloud/Devops/Data/ML/… So for example when someone says that they’re having trouble with some technology, say Argo, know that that means “workflow management” and direct them to the right solution within our product.

    There’s a lot of incidental complexity here that takes a while to learn.

  3. Are intellectually curious, comfortable in startups, and excited to be creative and invent new systems

    There’s really nothing in place to define how to do the job. Hopefully this excites rather than scares you. Also, we have a distinct communication style (direct, critical, thoughtful) and hopefully you click with that.

This person probably doesn’t exist, so we’ll happily settle for two out of three, and we’ll just build a team to round things out. Probably this team looks a little like …

  • Account Executive

  • Sales Engineer

  • Field Engineer

Interviewing AEs is Hard#

We’ve got good candiates for Field and Sales Engineers. AEs are harder for us to connect to though. There are lots of great candidates out there, but it’s been harder to come to a sense of conviction with an AE so far.

My experience interviewing AEs so far has been that they say fairly generic things like:

  • I’ll succeed by finding the buyer, figuring out what their pain is, and then demonstrating how we solve that pain

  • I did this with big name company X, where I built the relationship over many months, and built the deal to $X million

  • We should sell where the money is

Everyone says these things, and while I wholeheartedly agree with these points, they don’t differentiate a candidate, and they don’t say anything specific about our situation. My assumption is that early stage startups are different from each other, and that what works for one is unlikely to transfer to another automatically.

So, AEs that I interview, here’s the cheat code:

  • Assume that I know more about sales than a typical engineer (you can save time by not explaining basic concepts)

  • Get to a point in our conversation where we are conversing about strategy at a non-generic level.

    To do this you will likely need to …

    • Become a lot smarter about our situation pretty quickly, this probably means asking questions that are useful to you

    • Pause … and think

  • If it looks like I want to say something, notice, and open some space. I’m very interested in how well we can communicate.

The number of otherwise qualified AEs that come in and give the impression that they have all the answers (despite not knowing much about our situation) is odd to me. My guess is that they’re assuming that I’m looking for someone to say “everything’s going to be ok, I’ve got this” convincingly enough and so that’s their main/only message. However, to me saying that with conviction but without understanding our situation is a strongly negative signal.

What I’m actually looking for is someone who can demonstrate that they’re able to think and solve my problem specifically, not today, but over many months after failing quickly many times and thinking through new strategies. My assumption is that any answer you have today is likely wrong, so if you have strong conviction on that answer I’ll probably assume that you’re mentally inflexible.


To accelerate the interview process a bit, here are some frequently asked questions by sales folks:

  • Q: What is your runway?

    A: We have two-ish years of runway, assuming we don’t make any money

  • Q: What are your goals?

    A: I’d love to get to $5mm ARR in that time (but you tell me what you think is feasible, and we’ll adjust strategy together) probably with a mixture of small and large deals.

  • Q: How much room is there to grow? (could I end up managing sales?)

    A: Yes, if you’re good. I don’t promise anything though. Honestly, if you’re really good then you can have my job :)