Benefits of Becoming My Own CTO

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Learnings from a solo, (formerly) non-technical, female founder.

By Abigail Holtz, Founder, Affinity This post originally appeared on Medium.

As anyone who lives in the Bay Area can tell you, looking for a CTO in the Silicon Valley these days is probably one of the biggest cliches. With the amount of money that has been poured into tech over the past 5 years, there has been a proliferation of startups and no shortage of great opportunities — making the demand for talented technical people higher than ever.

So when I left my job at Google to start working on an idea I had in the fashion personalization space, I was immediately faced with this tough reality. I worked my network and did a bit of “founder dating,” but in the end I decided to opt out of the search. Finding my perfect technical partner and convincing them to take a chance on me — when all I had was an idea — seemed like a nearly impossible undertaking. So I tried something different. I figured that with my brain, the internet and a handful of technical close friends to call on (thanks guys!), I could learn everything I needed to get my startup off the ground. And with that I set off to become my own technical co-founder.

Over the next year I transformed myself from a product manager into a pretty savvy data scientist and a reasonable python programmer. I schooled myself on everything I would need to build out my clothing recommendation technology. I taught myself to code, brushed up on my statistics skills, and read anything I could find on recommender systems. And then, with my newly-minted technical abilities, I started to work on making my product vision a reality. The months that followed were filled with tons of trials, errors, experiments, and learnings — many of which I will likely share in future posts — but it all culminated in the beta launch of Affinity (my data-driven fashion recommendation service that delivers better recommendations than a personal stylist!) a few months back.

Looking back, the decision to become my own CTO has had all sorts of ramifications on my business. Some of those effects were great, others not so great, some expected, others not so expected — but overall interesting enough that I thought I’d share a bit on my experience. Today I wanted to talk about the benefits, though if you are interested in challenges and learnings, stay tuned… I’ll be sure to cover those later. Now on to those benefits:

Learning to code made me self-sufficient — and efficient

The biggest benefit of becoming my own CTO, was the combination of self-sufficiency and efficiency. In a startup, time/resources are super scarce, so being able to do something quickly myself rather than having to open a feature request, create a spec and explain an idea in depth saved me a ton of time. These days when I have things I want to test or build, I don’t have to rely on anyone to do it for me. I can do it myself, often in a fraction of the time it would take to delegate.

As my company scales, it will of course be important for me to be focused on other parts of the business and have experts focused on their respective parts of our technology. But in these early resource-constrained days, knowing how to build things myself has been a big deal for moving the business forward quickly.

Getting close to the technology made my product better

This was so surprising to me because in the past I’ve worked on similar problems with similar technology (and been pretty involved on the technology side), so I didn’t think that doing the technology development myself would drastically change the way I thought about the product/problem. But contrary to my expectations, I found that when I was knee-deep on the tech side (specifically on the data side), I would find patterns, inconsistencies, or just get curious about why something was some way — and it would get me thinking about our approach or the general problem in a totally new light. Ultimately, my expanded technical understanding of the problem not only improved the quality of our technology, but also has had a daily impact on how I think about the product and our vision going forward.

Having to build it hyper focused me

I’ve always been a very focused product person, but having to build the technology myself (in addition to running all other parts of the business) forced me to confront the tough questions with even more rigorous focus. I had to ask things like: Can we make the feature set even more bare bones? Are there existing tools/software I can use instead of building X myself? How can we test if Y will work without building it out completely? What things are good enough/OK to ignore? Do we really need an app? Compromises weren’t fun for sure, but having so little time really made me think through every little decision to make sure it would count. And now when I look at other companies in our space (most of whom have orders of magnitude more resources), I’m pretty confident this extreme focus paid off. We have a cohesive product that resonates with our target audience and a technology that performs better than our competition.

Doing it myself gave me real credibility

You might think that having worked in tech my entire career (coming up on a decade!) and being a product manager at Google would have given me enough credibility, but you really gain another level of respect when you show people you can do whatever it takes to build a successful business. When I first started my startup, people thought it was a cool idea. But that was just it. An idea. No one was rushing to quit their job to join me on it. Or invest major cash into it.

But now, when I show people what I’ve built and tell them how I did it and how well it performs, all sorts of people — engineers, angel investors, product people, press — are impressed. That doesn’t mean getting investors, building the team and getting media attention is/has been easy (yet!), but the credibility I’ve gained from getting the business where it is today has definitely made things less hard. :)

Now that I’m looking for a CTO, I know exactly what I need

The final benefit of leading the technical side myself was that it helped me figure out exactly what kind of CTO my business really needs. When I started out, I thought our ideal CTO would be a deep machine learning expert with a PhD and years of industry experience. While I still think he or she may have that type of background, I would now put more weight on other skills/traits.

Having built our technology from the ground up, I’ve seen firsthand how good ideas — ideas that come from deep analysis and critical thinking — often perform better than elaborate technology. So now that I’m starting to look for someone to take over the tech helm, I’m first-and-foremost searching for someone with a curious, analytical mind and a passion for solving problems. Although I know well that experience and technical ability matter a lot, today I’m more confident than ever that our startup will succeed or fail on good ideas, not just from the product side but from all parts of the business.

Final takeaways?

As you can probably tell, becoming my own CTO — at least to get my business off the ground — was huge for me. Not only did I gain technical skills that I’ll undoubtedly use throughout the rest of my career, I also became a better product person and leader. Perhaps there are other, more efficient paths I could have taken to get me where I am today, but all in all I have no regrets. So for those of you who find yourself in a similar situation to the one I was in when I started my company, I encourage you to consider the route I took. It may not be conventional, but it has some upside! — Hope you enjoyed reading about my experience. If you are curious, you can learn more about me (on Linkedin), my company (Affinity), and the challenges and learnings I’ve encountered as a single founder (follow me here on Medium. to catch the articles I have coming over the next couple weeks)!

If you have questions, comments or want to learn more about the CTO opportunity(!), drop me a line — abby (at) tryaffinity.com.


Abigail Holtz is the Founder & CEO of Affinity (tryaffinity.com), a data-driven fashion recommendation service. Throughout her career at Google and startups, she has managed over 10 e-commerce products – including Google Catalogs, Boutiques.com and Glamour's Ask a Stylist. Abby has a deep love for building consumer products and is passionate about using technology to improve the way we shop online. And when she isn't thinking about the future of retail, you can find Abby hosting dinner parties, attempting to learn German, trying to keep her garden alive or traveling with her husband.