Career Journeys @ Twilio: Fueling Growth With Learning

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March 27, 2024
Written by

Name: Justin Kitagawa

Role: VP of Engineering, Product Platform

Home Base: San Francisco

Fun fact: Justin spent some of his childhood living in South Africa. He’s frolicked with cheetahs and lived to tell the tale.

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Career Journeys @ Twilio: Fueling Growth With Learning

Justin Kitagawa has a wealth of experience under his belt, including serving as principal of his own software engineering consultancy and directing the engineering practice at an infrastructure-as-a-service (IaaS) company. Across his 20-plus years in software, Justin has always viewed new experiences as learning opportunities.

So, after nearly six years at the IaaS firm, Justin knew he needed to move on to keep growing. "I was looking to reach the next level of scale from what I had been operating at, and there were a handful of companies that I was considering," said Justin. "I wanted to work at a platform company that used a service model, and Twilio captured my attention early on, but I had such a naive view of telephony. What Twilio was doing seemed almost like magic."

The vice president of engineering at the IaaS company was friends with Twilio co-founder Evan Cook and spoke very highly of the company. "That helped me make the decision," said Justin. "I was curious to learn how this technology worked, so I just had to get an interview there."

Taking a Chance On a Good Impression

During his first interview, Justin met with Twilio's vice president of engineering and was impressed by what he heard about the organization and how it built revolutionary tech tools. Unfortunately, Twilio didn't immediately have an open role at Justin's desired level. "I worked really hard to become a director at my previous company," he says. "And I didn't want to move backward." 

However, platform services is an area he needed to gain more experience in, and Justin saw this as an opportunity, not a drawback. "The ability to learn something new pushed me to take a bet on the company," he recalled. So, in 2014, despite a lack of director-level openings, Justin began his Twilio journey as an engineering manager for the platform services team. 

A Career Journey Is a Pyramid, Not a Ladder

Justin's varied experience as a software engineer, architect, project manager, and product manager helped him hit the ground running at Twilio. Although he hadn't expected to start at the manager level, he didn't let that stop his momentum. "A career path is not always going to be a straight line," Justin says. "You should always have intent about your career path, but be open to the detours." 

A friend told Justin to focus less on how he got to Twilio and more on the impact and legacy he would create throughout his Twilio journey. "That gave me the confidence to bet on myself," Justin says. "I was curious to learn what I could do."

Justin joined Twilio when it was still in late-stage startup mode, which meant there was plenty of room for growth and optimization. Although he added to the platform services team's technical capabilities, he noticed they lacked management and process. He quickly recognized that his role as a manager was to fill gaps in his team's strategic needs. 

"There shouldn't be just one way you operate across the board. You have to tailor it for each and every situation," he says. "I realized early on that I needed to emphasize process and execution." 

One of Justin's first challenges was stabilizing the platform services' systems. "By standardizing processes, I could demonstrate what we could accomplish if we applied software engineering discipline to what had previously been a non-software approach," he says. "In the end, we built self-service systems to empower individual teams to run autonomously and increase efficiency." 

Getting Basics Back on Track

A VP in the company, who became Justin's sponsor, recognized that Justin was operating at a director's level and wanted to elevate him to that role so that he could increase the scope of his contributions. Within a year of joining Twilio as an engineering manager, Justin inherited the API team (now the Edge platform) and was promoted to director level managing three R&D teams.

Over the next two years, Justin learned a lot about managing teams and the engineering organization within Twilio. He grew into a senior director role and became a vital and strategic support for the individuals he reported to. "This trajectory gave me a lot of neat, interesting opportunities," he says. "I found myself adept at rallying people together, organizing, and executing."

He also found himself without a leader, who had to step away for personal reasons. Without hesitation, Justin stepped up to fill in, which gave him an expanded line of sight into what the VP role entailed. "My experience as acting VP helped me prepare to become a vice president, myself," recalls Justin. "At the time, I was operating at three levels at the same time: as a VP, at the director's level, and at the same time, I was also directly managing a team." 

Justin believes you ought to have experience in a job before managing others in that role. It's that awareness that helps Justin refine his management style and philosophy. "It's easy to operate with blinders, especially in this fast-paced environment," he said. "I knew how I liked to be treated as an engineer and what has encouraged me. That's really helped me think strategically about what's working and how to communicate with others."  

Indeed, pausing to reflect is the mark of a great leader. "It's essential to take stock and hold ourselves accountable about what we're doing well and what we're not doing well," he says.

Taking Lead on Projects and People

In early 2021, Justin took a lateral move into another senior director role. Twilio's chief product officer at the time identified an opportunity for a new product platform inspired by the "tragedy of the commons," which states that when you have a shared resource, it's never distributed evenly. 

Over time, individual product teams built services that have since become critical common building blocks used throughout Twilio. Well-intentioned product teams having finite capital made rational choices to divert funding to higher-priority projects. This left core building blocks underfunded, unfunded, and, at times, effectively unowned. 

Justin co-founded Product Platform to overcome this problem. By creating an R&D organization to own these critical platform building blocks, Justin helped stabilize foundational services used throughout Twilio while countering the tragedy of the commons. "Our focus was on operational excellence — to make sure that common building blocks used throughout our products worked seamlessly so that we can provide a consistent, reliable user experience to our customers," he says. 

Because Product Platform was initially smaller than Justin's previous team, Justin had another opportunity to think about what worked, what didn't, and how to organize his team. The vision of the Product Platform organization resonated with Twilio's product teams, and soon they grew from one to four R&D groups. Product Platform was able to absorb these groups successfully because of the work put into managing the organization up front. 

"We built systems to track who worked on which team, what initiatives are being addressed, and how much effort is spent on each," Justin says. Big wins over nine months, which resulted in clearer visibility into engineering operations and processes, helped Justin officially earn his role as vice president. 

Encouraged to Step Up

"There are always leadership opportunities here," Justin says. "In general, if you want to lead, you're encouraged at Twilio to do so." A big part of Justin's role today is inspiring that ambition in the next generation of leaders.

"I feel that I've helped identify, nurture, and grow some really talented people who've gone on to make an impact at Twilio," he says. "I've always viewed that the best way to scale is to teach the people we manage to eventually assume our responsibilities, so they can teach the next generation of leaders. And so on and so on."

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