The Nuts and Bolts with Franklin Angulo

Franklin Angulo is the Chief Architect at Squarespace.

Franklin Angulo is the Chief Architect at Squarespace.

What was your path to engineering?

My dad was trained as an electrical engineer in the US and he worked for Frederick Electronics installing telecommunications equipment for the US Army in various countries around the world, including Nigeria, Venezuela, and Chile. Before my twin sister and I were born, my mom and dad moved back to Costa Rica because they wanted us to grow up surrounded by our extended family. However, my dad couldn’t find a job that matched his skillset, so he founded his own hardware/software company.

Given that the company was based out of our home, I had daily access to my dad, and in time he taught me how to build computers and how to write software.

The software application that my dad ran back then was built on top of an old technology and I was tasked with refreshing it. After taking a summer Java course, I built a Java Swing application to replace the existing application—some of that code is still being used today by hundreds of customers. I will never forget the day that I discovered that recursion was possible when I decided that I needed a function to call itself. After that, I became fascinated with programming and asked permission to teach myself AP Computer Science my last year of high school, since it wasn’t offered as a course at the time.

After graduating high school, I was very lucky to receive a scholarship to attend college in the US where I pursued the fields of Computer Science and Actuarial Mathematics.

You spent time at EMC (now Dell EMC) and Amazon early in your career. How did those experiences inform your path as an engineer and leader?

My family and I were over the moon when I received an offer from EMC prior to graduating college. We didn’t really understand the laws governing employment for non-US citizens and thought that I’d have to go back to Costa Rica after graduation. I was overwhelmed upon joining, but my teammates were welcoming and kind, and they helped me learn and become a productive member of the team.

Most of all, I remember being very curious while at EMC. For example, one of the teams in our organization was suffering from performance bottlenecks in their C++ application and I pushed myself to learn how to use profilers to be able to pinpoint the offending code.

Amazon was a completely different environment. It had a much faster day-to-day pace and much more workload. In hindsight, I may perhaps have suffered from impostor syndrome. For the first few months, I would work nights and weekends trying to learn how to write software at Amazon, use all of the tools, and finish my projects. In time, I developed bonds with some of my teammates and it helped me to have them as a support structure. I fondly remember our daily Starbucks coffee/tea runs to talk about the problems we were facing.

I also vividly remember my first big launch. I was stressed out but my teammates came over to my desk, sat next to me, and reassured me that everything was going to be okay. We deployed the code, monitored the metrics and logs together, fixed some bugs, and successfully rolled out the project by the end of the day.

At Amazon, I was first exposed to discussions where engineers would butt heads, sometimes disrespectfully. As an introvert and naturally shy person, I found it very challenging to navigate this, but I eventually was able to find my voice and stand up for what I thought was right—both culturally and technologically.

You joined Squarespace in 2013 as a Senior Engineer, and helped build and subsequently led the Infrastructure organization. When did you realize that you wanted to focus on technical strategy and architecture?

I realized my dream of living and working in New York City by joining Squarespace in 2013. It was quite a small company back then with many technical challenges. In my first few weeks, after finishing a few bugs and small projects, I grew anxious because I had to deploy my code but there were no dashboards I could look at to monitor latencies and errors.

This led me to build large-scale monitoring systems based off of open source software that all engineers could use. In the following months and years, due to Squarespace’s massive business growth, we had to similarly rebuild many components in our stack, ranging from build and deploy systems, to databases, to compute platforms, and even the size and location of our physical data centers.

At Squarespace, I was almost always able to focus both on developing my management skills and steering towards technological changes. However, the balance became much more challenging as the infrastructure organization grew. I had to invest my time in recruiting efforts, communications, and helping develop the careers of the managers reporting to me.

At the beginning of 2019, after years of focusing solely on management responsibilities, I started to get the itch to write code, design software, and lead technological change again. I thought long and hard, and read many articles—including this one—and I realized that I would find it fulfilling to focus on technical strategy and architecture for a few years.

You’ve been at Squarespace for several years and recently returned after a year’s absence. What makes Squarespace special to you?

During my interview process in 2013, I explained to John Colton (Squarespace’s SVP of Engineering) that I was looking for an opportunity at a smaller company that wouldn’t restrict me to just working in one area of code—I wanted to expand my understanding of how to operate a business and make it grow through technology.

Squarespace is special because it wildly exceeded my expectations in this regard. In the past five years, I’ve had to push myself as an engineer more than ever before. I had no prior experience building and operating physical data centers, for example. While I had used microservices at Amazon, I had never truly thought about what it would take to build a microservices framework from scratch. Similarly, I had used virtualized compute, but containers and orchestration systems like Kubernetes were brand new ideas that I was exposed to.

I’ve also had to wear different hats throughout the years. For example, I acted as a product manager leading our internationalization efforts and launching support for payments in multiple currencies. From a management point of view, I grew an organization from one team of five engineers to more than 100 engineers across 20 teams. And in terms of org design, I built out entirely new functions like site reliability engineering, technical program management, and technical writing.

Being able to do all of this while at the same time seeing the business grow from fewer than 200K customers to millions makes it even more special.

What recent technology (hardware or software) has excited you?

In the 80’s and 90’s I grew up hearing about Franklin Chang Díaz, a NASA astronaut from my hometown who flew aboard the Space Shuttle missions multiple times and helped in the construction of the International Space Station. I found it surreal to watch the shuttle launches and would dream about becoming an astronaut and exploring outer space. Many years later, glued to the SpaceX live stream, I watched the spectacular Falcon Heavy simultaneous side booster landings. I was in awe thinking about the sheer complexity of this monumental achievement.

What are your non-tech passions?

Fútbol (soccer), running and traveling. I play pickup soccer games on the weekends, and enjoy commuting by running from our office in West Village to Long Island City—when it’s not too cold outside. I travel a lot to Costa Rica and if I’m on vacation, I’m most likely at one of the beaches.

When possible, I try to plan trips that include all of this. Last summer I went to Spain, visited the beaches in the island of Menorca, attended the Champions League game between Atlético Madrid and Juventus, and ran around the El Retiro park in Madrid.

What does the Chief Architect role entail?

As an architect, I’m focused on achieving Squarespace’s short-term and long-term goals through technology. This means working closely with executive and product leadership to define the areas of focus for our product roadmap and business strategy, and then figuring out the best way to match our technology to those. To shape this technical vision for Squarespace and continue our technological evolution, I work very closely with the principal and staff engineers across all sides of our engineering department.

Most recently, I’ve been discussing approaches to speed up the modularization and/or decomposition of the core functionality that still lives in our monolithic application, ideating ways in which we can augment our data platform and event pipelines to provide engineers with the product analytics they need, and agreeing on best practices for experimentation and feature flagging of the features exposed to our customers. I’ve also led the effort to roll out a quarterly planning process across engineering, product management and design to set clear goals for the outcomes we’d like to see as a product organization and align team roadmaps to achieve them.

Do you have a super power?

My grandmother says that I have the ability to enter a room and make people smile. She’s very generous with her compliments. However, I do recognize that I’m constantly smiling and that there are various studies that indicate that smiling is contagious. So, she might not be wrong.

Source: Squarespace