Dear Birb Street,
I am the non-technical founder and CEO of an early-stage startup. A few months ago, after my technical co-founder and I had split up, I hired a CTO for my startup from AngelList. I was pretty desperate for technical talent, had 0 experience hiring, and lowered my bar; so, not a good mix.
It’s become apparent that things aren’t going to work out with this CTO, so I’m trying to hire a lead engineer ASAP so that I can part ways with this CTO. However, this hire feels particularly tricky because I can’t lean on my current CTO to help out since he’s actually the one I want to replace.
One of my biggest issues with my current CTO is he just doesn’t do anything on his own. He comes to me with more problems than he solves and doesn’t take any initiative. I feel like I have to manage him much more than I’d like.
How should I navigate hiring his replacement, and how do I make sure not to end up in the same situation again with my next hire?
— Hirer’s Remorse
Dear Hirer’s Remorse,
The situation you’re in sounds quite difficult: Hiring well is always hard; hiring highly sought-after engineering talent well is even harder, and doing so without support from your team as a non-technical founder is harder yet.
Effort-wise, I've heard that hiring should take up anywhere from 25% to 50% of a founder's time, so since you can’t rely on your CTO for help, I imagine you’ll be in the upper part of that range. I highly recommend reaching out to any advisors or friends that might be able to help.
Below are some hiring principles that my startup friends and I have found useful; however, every hire and situation is different, so please take with you what is helpful and leave behind what is not:
Develop a clear talent profile.
Your current CTO is likely a great fit for different role at a different company. That’s why it’s important to know what you want: You can filter out a lot of folks who aren’t a good fit by sending strong signals of what a good fit is. In the early stages, I imagine you're looking for someone who's a strong generalist and can work across all parts of your tech stack. Even though that's a fairly general description, the set of people who actually fit the bill for your company is quite narrow; when it comes to engineers, some positive signals might be that they aren’t happy with shipping slowly, that they have worked at startups before and like the pace and accountability, or that they love tinkering on side projects.
Start with your network.
Given how hard it is to hire well, it's best to start with people who aren't complete strangers, people who can be vouched for by someone you trust. I've heard that, often, up to the first 10 hires at a startup are from the team's own network. At this (early) stage, nothing's better than a candidate that someone you trust is excited about, and that’s doubly true if you’re not confident in your ability to directly assess their technical ability. If you find yourself in the late stages with a candidate from outside of your network, don’t cut corners on the reference or background checks. There are a lot of hiring horror stories out there, ranging from unreliable references to outright impersonation, so trust your gut if something feels off and do the due diligence.
Early hiring is very high touch.
The more competitive or skilled the talent you’re trying to hire, the higher touch the hiring efforts need to be, especially at the early stages. That candidate isn’t just another applicant in your system: They’re someone who could change the trajectory of your company. Don’t aspire to the standardized hiring systems of late-stage companies; after all, many of them are trying to recover the high touch hiring practices they had when they were smaller, and the reason they can’t do that anymore isn’t because they don’t want to, it’s because they aren’t able to due to the difficulty of scaling such practices.
Don’t settle.
No matter how badly you're feeling the burn of an unfilled role, it’s critical that you don’t lower your standards. The earlier the hire, the more important that they raise the bar in some way; they have an outsized ability to impact your company, and if you’re not careful, it may not be for the better. The tradeoff you make when you settle to fill the role faster almost never works out because a bad hire will make your life harder in ways you haven’t even imagined yet. An extra pair of hands doesn’t always make the work go faster!
There’s a lot more to hiring than the topics covered above, but I hope they at least provide a useful starting point for you. Best of luck; you’ve got this!
Sincerely,
The Birb Street Journal