How I Got Here: Nico Westerdale’s journey from dot-com era designing to fractional CTO

Nico Westerdale’s tech career didn’t stem from an IT degree or a bootcamp graduation like many other technologists.

He began coding at 9 years old on a ZX Spectrum, a British computer, in the 1980s and was taught BASIC by his dad. For more than two decades, he’s worked for tech companies spanning from dot-com era startups in New York City to leading projects at Comcast.

Most recently, after more than two years at Gopuff leading its engineering teams, Westerdale has gone into business for himself as a “fractional CTO,” helping startups in the early stages of their work define their product and support their growth journey.

Westerdale joined Technical.ly for a career-focused AMA on our public Slack channel this week. You can find the full version of it over in that channel where we talk programing languages, bootcamps, his go-to interview question and more. Below, you’ll find a condensed version of our conversation, edited for length and clarity.

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As someone who is self-taught in tech — your degree is a BA in fine arts — how did you get to a tech career?

A lot of it was self directed. I remember copying code out of the back of Crash magazine and trying to get programs to work. Most never would due to typos or me not understand what I was typing. This is before you could just look things up on Stack Overflow, of course.

I got my first break at a multimedia company after college writing programs in Macromedia Director, which was a precursor to Flash. In 1999 I moved to New York City and got a job at Rare Medium, which was a huge consultancy. They were hiring everyone and anyone at the time — if you knew Dreamweaver, you would get a job. There were very few degree programs that taught all of this and I quickly realized that I had a lot more hands-on experience than those coming from a comp sci or maths background.

At the time, what did a tech career look like?

Well, I don’t think anyone really knew. There was the more formal IT or technical careers, but the web model was so new. I was hired as a “design technologist” which roughly equates to a “frontend engineer.” Product mangers were called business analysts. We had information architects and designers, the term “UX” was not a thing. There was little UX research.

In your first few years, did it feel like things were changing quickly? Even now, we hear that different languages are more or less relevant year to year.

When I started out in 1999, there were no real frameworks from development, we were just coding raw scripts. Then we all jumped on to using Prototype, and then quickly after jQuery. With those frameworks, Prototype was a time saver, but was poorly thought through. But it paved the way for the next framework to come in and do it right. jQuery ruled for a decade, and you still see it, of course. And then now we see similar things with React, Angular and Vue all coming in and learning from each other.

The really interesting thing is that right now there is no clear leader in those three areas, they all excel in slightly different ways. But as we move forward, we’re looking at the levels of abstraction go up each time. CSS being replaces with Sass, we have compilers on the front end. That’s akin to having a higher-order programming language.

Tell us about your time at Gopuff, which you joined in early 2019. They’ve been growing quickly for as long as you were around.

Gopuff founders Yakir Gola (left) and Rafael Ilishayev cut the ribbon on their renovated offices in 2017 with the help of Philadelphia Mayor Jim Kenney. (Photo via Twitter)

Gopuff was a lot of fun, and probably the fastest I’ve ever gone in a startup. It was very difficult to manage the growth of it all. The funding of course was a driver, but it was really the reflection of the huge ambitions of the two founders. It’s a lot more stable now that the engineering team is over 200 people, but in the two and a half years it took to get us there, it was bumpy. We weren’t even on two-week sprints for the first year, we just ran a kanban as we were going so fast. We threw code at prod all day, just trying to keep up with it all, then gradually we defined more teams and layered in process. So I went from telling everyone to go faster to telling everyone to slow down, once we had the capacity to do that.

[Just before Gopuff, Westerdale worked as CTO for Old City healthtech startup IncentFit from 2015 to 2018.]

IncentFit was a lot more measured. We had very tight resources as we bootstrapped it, so we were more deliberate in who we hired exactly when. They both had a growth curve, but the risk factor was different in each case. I think the best analogy I heard at the time was that it was like a sports team, we were all there because we wanted to win. Gopuff was an outlier for sure. I remember feeling like it was a bit like 1999 and the first dot-com bubble.

So, you’re working for yourself now. Tell me what it means to be a fractional CTO.

It took a lot of introspection to get to this point, but I had a realization earlier this year that I really did like the first part of tech startups, defining the early product and helping to put togherther an MVP or start the growth journey. And given that I looked at the positions out there, I wanted to work with small companies, but all of the roles on the engineering side require coding. I thought that if I could spend a quarter of my time with one startup, providing technical leadership and hands-on management to define roadmaps, hire people and work with founders to make the right decisions, then that would suit me perfectly.

It’s just not a full-time job in one startup, so I would have to do it in three or four at a time, hence “fractional CTO.” From talking to a lot of startups, I think there’s a real value here that’s often missed. Many startups hire a really good senior engineer to be their CTO. That’s all well and good, especially on the coding side, but they can run into problems in getting the product to where it really should be, and hiring the right people at the right time to make it happen. I’m trying to stay away from shipping code right now, especially in these roles. If I go down that path I’ll end up going full-time at a company and won’t be able to work with several at once. It’s more my role to set the direction and hire the team to get the job done.

What advice can you share for technologists who might be feeling like it’s time to either work for themselves or make some sort of big pivot?

I’m a big believer in leading with your heart and be true to what you’re good at. One question I always ask in interviews is “what are you best at” and it’s rare that I get a really good answer. If you can find out what you’re best at then find a way to excel at that, and find a position that lets you do it, whether that’s at a big corporation, going it alone or something in between. Most people answer “I’m great at learning new things,” which may be true, but it doesn’t differentiate you from anyone else.