Ask a Founder: How do I hire someone and have them succeed?

Founders can make or break a company, and getting over oneself is the key.

April 12, 2024
I know it's time to hire a sales leader. I'm the bottleneck on closing deals and getting more revenue in the door. But I've now hired two people who got past me, the board, and everyone else and they've failed. What's happening? How do I hire someone and have them succeed?

It’s possible that even the most seasoned founder goes through some version of this question. And it might be my favorite problem, because it’s the one I also had to get past in order to scale a business. It’s never “do we have enough drive”, and if you got funding and are asking this question, you probably have a good enough product in a hot enough market to win. It’s whether or not you, the founder, can mature quickly enough to figure everything out fast enough to win. It’s whether or not you can beat your ego. Founders can make or break a company, and getting over oneself is the key. 

Now, in this question there are actually four questions lurking that need answers:

  1. Do I actually know how to close a deal in a way that’s repeatable or am I deluding myself?
  2. Have I hired any AEs (account executives) who are productive? 
  3. Is it actually time to hire a sales leader? 
  4. What’s actually wrong in the hiring process, assuming the answer to the first three questions is ‘yes’?

For the first, a repeatable sales process means that I can write out exactly what someone needs to do in order to go from generating a lead to getting on the phone to multiple demos to technical proof of concept to business agreement to contract to close (retention and expansion is a different beast). If you can’t write out that process, with the exact words and script and series of actions an AE needs in order to do the same thing (with training of course), then you are not ready to hire an AE. Keep at it until you can write out a process that works, again and again and again.

Senior leaders don’t invent; they scale. Invention is the founder’s job.

Then, when you are ready to hire an AE, you need to train and support them. That does NOT mean micromanaging them. That MAY mean throwing them into sales calls conducted in your industry's jargon. The original AE team at my last company was ultimately successful, but they spent their first three months completely overwhelmed. And then all of a sudden, they weren’t.

On the third point, and as I mentioned in a prior article, senior leaders don’t invent; they scale. Invention (in this case, definition of the end-to-end sale) is the founder’s job. Sales leaders should only be hired in the case of 1) a founder being able to write the proverbial playbook, and 2) having a pair of AEs who are productive.

This leaves us with the hiring process itself. Assuming everything else is in a good spot, how do you hire for a leader, especially in a division as tough as sales and in an industry where more than 50% of retained searches fail and have to be redone? Here are a few techniques that have helped me in the past:

  • Back-channel diligence. This goes beyond checking references. Call folks that they’ve worked for and who have worked for them in the past. Call a former board member they presented to. If there’s a whiff of a fundamental mismatch, don’t try to rationalize it, just move on. Red flags could include things like two jobs where they lasted a year each, or someone who simply can’t articulate the specifics of a project even if they can talk about implementation theoretically (beware consultants!)., There will always be other candidates.
  • Presentations. Have them put together a short presentation, maybe 30 minutes, on what their first three months will be like. You’re looking for bone-dry content that shows they’ve paid attention to what folks have said throughout the interview process, shows they have a process in mind, and isn’t trying to wow you with fanciness.
  • Team. Top leaders bring folks with them. Can they tell you who they’re bringing? Specific names here are key, and you want FTEs, not consultants.

You say in your question that these failed hires got past you and the board. But really, as I wrote about in the article above, your board isn’t capable of helping here (even if they claim to be—it’s simply not what they’re good at), and your retained search firm just wants the hunt to end. But definitely use the data other interviewers are collecting (not opinions, data, like “they said X and it made me think they might not be able to do Y”) to validate or invalidate your hypothesis about a candidate. And when in doubt, pass.

So what have we learned? Get over yourself, write down a process, help someone else to learn that process, and then hire the leader. Not before. 

This is the end mark. You have reached the end!

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