We have a CTO, and so can you!

I was told that finding a CTO/technical co-founder in NYC was about as easy as climbing Everest with one leg, no O2, and carrying a dead elephant. Honestly, I like a good challenge, and doing impossible things has a certain allure to it. But this was…daunting.

Today, though, we did it, and I wanted to share that experience in tribute to how awesome the scene in NYC is right now, to all the people I met along the way, and to give a little bit of advice to other folks looking to climb the same mountain.

Starting at the beginning

Three months ago, Josh and I started knocking around the idea that grew into tutorspree. As the idea took shape, we faced a couple of problems: 1) We did not have the expertise to build a product ourselves 2) We did not know whether or not we were solving a real problem. Having just finished Steve Blank’s Four Steps to the Epiphany I was dead set on answering the second question first. Before we went off and spent money to either hire a developer or pay a shop to build something, I wanted to make sure that we would have a market that wanted what we were doing and would pay for it once we actually delivered. Besides, we needed to know exactly which features were necessary now, and which could be tacked on later.

Skipping ahead a bit

Suffice it to say that we spent much of the last few months on customer development, a topic which merits its own post, and at which I think we’ve done a decent job. About a month and change ago, we realized that we really did have a viable idea for a product, and that it was time to find the partner to help build it.

At that point, I shifted a major part of my time to tech specific networking, as did Josh. We emailed every person we knew who was even ancillarily involved in technology, I put up a job post on this blog, I started working my way through specific job boards that I thought would have the kind of people I wanted. I sent out hundreds of emails, and had coffee with dozens of people. I handed out a whole bunch of business cards, and got rejected time and time again. So how did we end up succeeding?

Know what you need, what you want, and who can tell you you found them

I learned a lot about interviewing back in the land of finance. Most important lesson I received came from my boss, Pawel, who took me to task for bringing a candidate in for a loosely defined position. He hammered me for not knowing exactly what qualities I was looking for and for not nailing down exactly who could tell me if the candidate had them. So Josh and I talked to my friend Jon Thornton, who is one of the brains behind ParkWhiz, about what exactly we needed. We knew we needed a crackerjack web developer, and could probably do without a guy who dreams in COBOL. Jon helped us refine that profile, and was good enough to offer to help us interview people.

This is critical: If you don’t have someone to run candidates through a tech interview, get one. We had two. Jon was able to assess web dev expertise for us, while my brother (also Jon) interviewed folks from a pure CS perspective (he actually does dream in code).

Get your pitch right

Remember that the developer you want to hire most likely does not think the way venture capital thinks, or the way that your customers think. You need to approach them the way you would a wounded bear - confident, cautious, and holding the right enticements. When it came time to put together our job posting, I ran it by developer friends, like Matt Insler. He gave me input on what would and would not attract attention. I practiced my “dev” pitch, and Josh and I gave a lot of thought to what we wanted to offer in terms of compensation. We were well aware that it would be a mix of cash and equity, and that there was no golden number for either.

Also, remember this: just because developers like to think about code first does not mean that they don’t like/have a head for business. Ideas are cheap, ideas that can make money are a bit pricier, and ideas which you’ve already proved have a willing market are even better. Every developer I met mentioned that they were surprised with the lengths to which we’d already gone to validate a customer base and business model, and it’s one of the key things that got them excited about working for us.

Talk, talk, talk…now listen

Every time I met someone new who might be interested, I probed how deep that interest went, figured out why they were interested, and tried to understand if they were a good fit. That led to a lot of conversations, and, in a lot of cases, led to understanding that that person was not a fit. If that feeling was mutual, I pushed for another introduction to friends that might be interested. I also asked every single person I met with to point out the flaws I had missed, to tell me what they thought we should do for technology, and how best to get there. All the talking I did was really just a way to get to that bit where I got incredible advice. Even people that weren’t actually interested in joining had amazing thoughts on how to make tutorspree better.

Big net = big fish

And each conversation I had spread my net out a little bit farther. I was mining 3rd and 4th order connections to find interesting people, and was discovering a whole lot of talent outside of the usual tech meetup afterparty. I learned to look for developers where they like to hang out - we went to hackers/founders events and watched their twitter stream, talked to the folks at hirelite, dug through HNHackers, sat at coffee shops and started talking to the guys with their heads down eclipse, and just generally pushed everywhere we could.

And people responded.

Good interviews have good structure

As I said above, you need to know the qualities you are looking for, and you need to work through them in an orderly way. Each person we interviewed went through a similar process. Prior to contact, we googled/linkedin/checked twitter and blogs. We then contacted the people we liked and conducted an initial phone screen or cup of coffee to gauge interest or basic fit. A conversation with the team member that hand’t yet met that person. If fit checked out, we did technical interviews, and if those went well, another fit conversation. If all that cleared, we started talking to references to challenge or verify our picture and what we’ve learned. If your candidate makes it through those steps…you may very well have a winner.

So let’s recap

1) You have a valid idea, and you’ve done your homework to prove it

2) You have a clear picture of the person you need

3) You line up the resources to assess the qualities you need

4) You go to where the hackers are, and you speak to them in a language they understand

5) You interview consistently, repeatably

6) You repeat steps 4 & 5 until you find the right person.

And then you succeed

Ryan Bednar, welcome to tutorspree.