How to Hire a CTO That You Won’t Need to Fire

Choosing a business partner impacts your business as much as choosing a life partner impacts your life. (that means a lot)


Where can I find a CTO? How do I vet a technical co-founder? Why doesn’t anyone want to join me?


As a CTO who gets asked this frequently, here’s my perspective on how to do this the right way.


Stop looking for an engineer


If the first question you ask me is “can you build this demo?” then I know that you’re just looking for someone to build your stuff. A CTO is not your code monkey (nor is an engineer for that matter), but it is someone who is responsible for the success of your company through technology. Your CTO may be an engineer and they may not be, but they definitely aren't looking to be treated as one.


Don’t hire. Partner


Having a co-founder is truly like being married, except that you spend much more waking time and hopefully less sleeping time together. Thinking of it like a partnership means two things.


First, don’t treat me like a hire. You are not hiring me to work for you. We are partners trying to create something great together.


Second, take the time to ensure that this can be a good partnership. Do you want to work with me for the next 5-10 years? Can we trust each other? Are we complementing each other well?


And just like marriage, divorce is going to be tough and will probably kill your startup.


Relationship first


Relationships sprout partnerships. Don’t be transactional and don’t partner with someone after 3 zoom dates. Take the time to do different things together. Both of you must be excited about spending a ton of time together.


I learned a lot of what I’m sharing here from my incredible co-founder. The first time we met, he invited me to cook dinner together. 6 years later, we remain best friends and still get together for family dinners. I’m the better cook though.


Understand what you need


CTO can mean a lot of things because technology means a lot of things. You need to understand what kind of CTO is right for you. This highly depends on your strengths and weaknesses and what your startup does. Some questions you should ask yourself:

  • Do you need deep expertise in a specific area?

  • Are you building a product-focused, engineering-focused, sales-focused, or something-else-focused company?

  • Do you need to build a big engineering team right away or keep things lean and mean for a while?

Casting a wide net is tempting, but it will only lengthen your search time and increase the chance of partnering with the wrong person.


Split equity evenly


This one drives me crazy. If you’re looking for a partner who will be as dedicated as you are, sacrifice as much as you do, and stick with you through a decade or two of pure agony, why would you offer them anything less than their fair share of the pie?


Here are some bad reasons to split unevenly

  • You’ve been working on this alone for a year now -> so what? If you’re really trying to build something big, then you are just 1% of the way there

  • It is your idea -> ideas have no value. Your idea will change multiple times. Execution is everything

  • You bring more to the table -> if this is the case then you are partnering with the wrong person or don’t understand the role of a co-founder/CTO

Splitting unevenly sends all the wrong messages. A major startup regret of mine is not offering a late 3rd co-founder an equal piece of the pie. He rightfully decided not to join us.


Understand what you’re up against


The market for technical talent is nothing less than insane. You are up against fierce competition. Do the research to understand what technical people get, and most importantly do not get, in big companies.


As a general rule of thumb, you should assume that a good technical person can go work for bigtech and retire after 10 years.


You can provide things to your CTO that they can't get in big companies, like autonomy, influence on non-technical aspects of the business, and meaningful connection to the company's purpose.


It’s about what they want


To be persuasive you need to understand what the other side wants. There are 3 common reasons for someone to join a startup as a CTO.

  • Building - They want to build things from scratch

  • Vision - They believe in the vision

  • Growth - This is the right growth opportunity for them

Dig deep and understand what would make them leave their awesome job to join your tiny unfunded startup. Fight hard for someone who wants all 3.


Build a network, you won’t regret it


Stop posting on Facebook and Hacker News hoping to find a CTO there, I’ve never seen this succeed.


The way to find a CTO is by investing in your network and getting to know smart people. How? Take one engineer that you know for coffee and go from there. Engineers know other engineers.


Be genuine about getting to know engineers and the engineering profession more broadly, you are building a tech company after all. I guarantee you’ll be pleasantly surprised by how much you can learn from engineers. This network will remain valuable throughout your entire career.


If you can’t find a single engineer to talk to, shoot me an email and I’ll help.


Have someone technical vet them


There’s little to no correlation between how well someone speaks and how well they can solve technical problems. No matter how excited you are, be diligent with technical vetting.


My advice here is to use both a technical person that you can trust to vet them, and work on a project together and see that they can deliver.


Don’t rush it


Legend says that it took the Airbnb founders 5 months to find their technical co-founder. Airbnb would’ve been just the same if it took them twice as long. Airbnb would likely not exist if they rushed it.


If you’re anxious to start building remember this:

  • Many startups build too early because it’s exciting. Your goal early on is not to build, but to validate and understand your business as a whole

  • Be creative, there is always a quick and simple way to build something without coding

  • It has never been easier to hire contractors to build things for you


Conclusion


No decision will make or break your startup as much as this one will. Here’s what you need to remember:

  • Look for a partner, not an engineer. Partnership starts with relationship

  • Know what you need and understand what they want. Give a fair share of the pie

  • Take the time to build a network and technically vet them. Don’t rush it