What’s The Most Difficult Position To Hire For Your Startup?

hard to find

I was an EIR (Entrepreneur in Residence) at a VC firm in San Francisco when I started my company. I told the partners at the firm that the success or failure of my efforts would hinge on my finding a great VP Engineering.

I had tons of contacts, and I had been in the industry for almost 20 years, yet I still knew it was going to be hard to find a great VP Engineering.

A great VP Engineering has a unique combination of skills that is very rare to find.

Here’s what you’re looking for:


A. A great hands-on engineer.


A great startup VP Engineering is still a practicing, hands-on engineer. You can’t just manage. You actually still have to design.

But being a great engineer is not enough…


B. Your great VP Engineering has to recruit other great engineers.


You’e going to have to build your team to be a great VP Engineering. That means you have to be able to recruit other elite engineers.

Great engineers only want to work for the best. If you bring on a B-level VP Engineering, then you’re only going to have B-level and C-level engineers. Needless to say, the success of your company is questionable at best.

A great VP Engineering isn’t just a great recruiter…


C. Your great VP Engineering needs to manage and lead your team of elite engineers.


Have you ever tried to manage and lead a team of really creative people? It isn’t easy.

Great engineers are, contrary to popular opinion, expecting to be led and managed. And to lead and manage an elite team of engineers you have to earn their respect.

That means your engineering team is going to have to respect your VP Engineering technically. And because it’s a team of creatives, your VP Engineering is going to have to manage a team of, to say it mildly, diverse personalities.

But there’s more…


D. Your great VP Engineering needs great business skills.


Probably the scariest employee in a startup is a VP Engineering that doesn’t have business skills. Oh the destruction that person can have.

“John”, the first VP Engineering cofounder of my company, didn’t have business sense. And John almost destroyed our company.

The last thing John ever said to me was, “I know better than you how to run a company.” John then stole the IP of the company (down to the slide deck we were using to raise money) and failed.

Jeroen, John’s replacement, had business skills. Jeroen became someone I could bounce business ideas off, and I would get reliably good advice in return. That’s what you want in your VP Engineering.

But there’s one more thing…


E. You want a VP Engineering that can present to investors.


When you raise money, it’s going to be you and your VP Engineering driving the meetings. Everything will fall apart if your VP Engineering can’t clearly and simply explain your technology to investors.


That’s a lot that you’re looking for in one package.


It took me, despite a deep network of contacts, about one year to find Jeroen.

But the craziest thing was Jeroen and I used to have the following conversation more than once:

Me: “I think the toughest thing to find is really good engineering talent.”

Jeroen: “I think the toughest thing to find is really good marketing talent.”

I was in awe of the technological prowess of great engineers. Jeroen was in awe of the skill required to do great marketing.


It just goes to show that the most sought after skillset for your startup is what you don’t have.


For more, read: Why You Need Fanatical Cofounders


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