The Changing Role of the CTO in a Growing Startup

Lessons from the Microsoft for Startups Global CTO Day

One of the main challenges as a CTO & Co-Founder is the journey from being the creator of a small founder team, to being part of a growing and much larger company. When I began my journey at Affinio, an interest analytics platform, I was one quarter of the founding team. Together, the four of us built everything. My function as CTO was essentially to turn ideas into reality. I was our only backend coder when we started out.

But the truth is, my CTO journey began long before we founded the company, back when Tim Burke (Co-Founder & CEO) and I worked together at a university lab. After learning the ropes we decided to break out and create our own R&D lab where other companies could outsource to us. We worked on a wide array of products from lobster scanners, to tethering solutions, to anti-keylogger software.

We learned so much, and each new innovation and product came from a moment of curiosity. One day we got curious about our customers and decided to look at what they loved on social media. We found huge and largely untapped banks of information on competitors, interests, and more. Affinio was born out of this moment of curiosity. Later, we worked to refine our product and fill in the gaps by bringing on board Phil Renaud, our front end dev, now VP Engineering, and Ardi Iranmanesh, our first research/analyst hire who is now our Chief of Staff.

But with any successful startup, over time things grow and change. When we got to the stage where we needed more than just the four of us and we had to hire staff, the tech team started to expand and different people had to take on different parts of our development process. It was no longer just myself working on the backend and architecture. And it was no longer just an in house team, as greater R&D demands also meant scaling and managing a remote team. For me, one of the major learnings at this point was letting go of things.

Affinio was lucky to be part of the Microsoft Accelerator in Seattle. The program’s uniqueness is that it works with mature startups. This helped equip us with the tools and knowhow that we needed to grow and scale our team and company. Support also extended far beyond the Accelerator itself, and today we continue to work closely with Microsoft. Just this month I attended the Microsoft for Startups Global CTO Day, and had a unique opportunity to meet and connect with other CTOs who are in a similar position to me, navigating their changing roles, and working hard to grow and scale their startups.

One of the highlights of the day was hearing how Adrian Colyer of Accel Partners transitioned from CTO and sole coder to having a VP of Engineering and then a VP of Product to help spread the load. He spoke about the growth of his team to 12 people. From personal experience, I know that at this point in the life cycle of a CTO, you can no longer continue to try and do everything, and need to take on some help. The talk also went further than my personal experience and gave insights into the future, including exploring the transition a CTO faces during and after an exit, and the tough decision of what to do after a company is acquired and there is no longer a CTO role to play.

Today, my biggest challenging is finding incredible talent, in order to grow and scale Affinio. This is a little trickier for us since we are based in Halifax, Nova Scotia, Canada, and there is a smaller pool of talent in this smaller city. So, I brought this dilemma to the Microsoft for Startups Global CTO Day. In particular, since not all talent can be in-house, one of our major challenges is how to source and hire remote workers, and how to keep them happy and motivated.

Hearing from other CTOs gave me some great insights into keeping remote teams cohesive and satisfied, including simple digital solutions like placing iPads around the office so you can see each other and chat, no matter where you are in the world. We also spend a lot of time on text chat with apps like Slack. Another thing I’ve learned is that sometimes you just need to be in the same space. So, this year, we are inviting our whole team, including remote workers, to our Christmas party and flying them all out to HQ. Scaling a startup is much more than just taking a product to new markets, it is fundamentally all about the team you set up and the people you partner with.

In terms of having a remote team, I’ve learned that it is crucial to be where your customers are and to bring customer feedback directly to the tech team. So, while our R&D and HQ are all in Halifax, Canada, we established customer-facing branches in New York and London. Although we don’t share an office, we work closely with these two teams. Their customer-focused roles mean they are able to gather a wealth of feedback and thoughts. This information allows us to continuously refine our product and grow our company.

Since the core of Affinio was always curiosity, we work hard to keep this sense of curiosity alive. On a personal note, I still spend a lot of my free time coding. In fact, around Christmas each year, I have a tradition of taking two weeks off for a “secret coding project”. My hope is that continuing to tap into our sparks of curiosity will create new projects that can help Affinio grow and thrive.

Being a CTO and Co-Founder comes with its own unique challenges. My main tips are:

  1. Build fast and don’t be scared to break things.
  2. Follow your sense of curiosity. Affinio was born from a keen sense of curiosity about customers and their interests.
  3. Make something that people actually want to buy – this comes down to market research. When we started we had a cool gadget, but after a year and a half of work we had a product that people wanted to buy.