April Underwood, 37, is the vice president of product at enterprise software company Slack, one of the hottest tech companies in the Bay Area. As the head of product, she partners with engineering leadership to oversee a team of around 350 people and is responsible for product vision and strategy at a company that boasts more than 5 million daily active users and a valuation of more than a billion dollars.
Underwood grew up in Amarillo, Texas, the daughter of parents who studied architecture. She was never pressured to pursue any particular career, although her family had a geeky streak. An uncle who worked at Texas Instruments encouraged her to play with the “Speak and Read,” “Speak and Spell” and “Speak and Math” toys when she was a kid. Another uncle gave her toys focused on learning binary. She wound up excelling at Advanced Placement chemistry and was later accepted to the University of Texas, Austin, for chemical engineering.
When Underwood decided to major in chemical engineering, she thought she would enjoy it because she had done well in classroom chemistry. But she quickly learned that the chemistry taught at school differed from its practical applications. “I realized a lot of those paths lead to working in oil and gas fields at refineries,” she said.
During her first semester, she knew she didn’t want to go further with it — but changing majors meant losing her engineering scholarships. “It was a huge leap of faith,” she said. “At the time it was really scary for my parents to see me do that, so I knew I needed to figure out a way to close that financial gap.”
She switched to management information systems, a business-centric major that enabled her to take classes in coding, finance, accounting and marketing. To make up for the lost scholarships, she got a part-time job.
Answering an ad in the college newspaper, Underwood got a gig in tech support for Austin firm TeleNetwork Inc., where she was paid $10 an hour.
“Customers would call in, I’d have to walk them through exactly how to fix their computers, then they’d have to hang up the phone and try it because they only had one phone line,” Underwood said. This was during the days of dial-up Internet, so Underwood learned to communicate clearly to customers what they had to do because she couldn’t walk them through it in real-time. She wasn’t intimidated by computers or technology. While doing tech support, she even saw an opportunity to create training programs for other people in the call center.
Over the holiday break she taught herself HTML coding from a book, and convinced her bosses to let her build the software. They agreed, and she built it.
Underwood’s senior year coincided with the height of the dot-com bubble — students were receiving lucrative job offers and signing bonuses and could have their pick of where they wanted to work. By the time she graduated, though, the bubble had burst, and a company she had interviewed with, Enron, was about to go under.
“I passed on a couple of job opportunities, and my peers and professors were angry with me because they thought it was very shortsighted of me,” she said. “It was like the world was crumbling.”
Still, with a background in business and coding, and internships at 3M and Deloitte, she scored a job at Intel in Oregon as a software engineer, working on Intel’s enterprise software.
Underwood’s software engineering chops landed her at Intel, but she quickly learned that she wasn’t content to only do software engineering. She was fascinated by the business side. She had an interest in marketing. She enjoyed and was good at communicating with people. She wanted to do something that combined all these skills. After a year at Intel she went to travel site Travelocity, again as a software engineer, but this time taking on more responsibilities, asking business questions, and serving as the bridge between the company’s technical and business teams.
“You’ve got to have your superpower,” Underwood said. “You’ve got to have the thing you’re really good at, because you need to be useful from day one, and you need to get your foot in the door.”
For Underwood, that ability was solving problems through code.
“But once you get there, if you have a broader perspective and some experience or interest in other areas, you’re going to stand out. That happened for me really quickly in my career, and it’s part of the reason I made the transition from engineering to product management a couple of years in.”
Navigating a path
Underwood moved around a lot in her career, working on enterprise-focused companies such as Intel and now Slack, and consumer-facing companies such as Travelocity, Google (where she spent two years) and Twitter (where she spent five years). During these job changes, she also transitioned from solely being a software engineer, to someone who straddled engineering and business, to being focused on product.
The key to her successful transitions, she believes, is she never made any major leaps.
“You have to imagine there’s a stone path, and you’re trying to get from one place to another,” she said. “If the goal is to get to product management of a consumer app, but you’re starting as an engineer of an enterprise app, then start by making the transition into product management at your own company, or in an enterprise company. Try to change one thing at a time, and it makes it a lot easier. It takes a few leaps and a few years.”
When to leave
Underwood often left companies when they were on the upward trajectory, a move that baffled some of her peers. Instead of clinging to a role at a company because of its prestige, or feeling that she had to “do her time” before she could move on, she asked herself three questions when deciding whether to take a new role.
“The first is to ask yourself, what will you learn over the next year at the company you’re at, versus what you believe you might learn somewhere else,” she said.
The second is how you feel about the product the company makes. In the case of Slack, Underwood had been a longtime user before she’d even considered working for the company.
And the third is to look at whether you’ve set up your existing team for success once you leave.
“I do think there’s a responsibility that you owe to your team,” she said.
Underwood chalks up much of her success to her curiosity. “Be really, really good at something at any given time,” she said, whether it’s engineering, business strategy or something else entirely, “and then get to know what the people next to you are working on, and develop relationships with them.
“That’s when you start to get a broader perspective. People who can do what they’re assigned to do, and anticipate the problems that are overlooked, those people are gold within an organization. So be good at the thing you’re good at, and be curious about the rest.”
Underwood lives in Marin County and enjoys hiking and baking. She is gluten intolerant and cannot eat most of what she makes, but it doesn’t stop her from baking it.
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8:15 a.m.: This article was updated to clarify that Underwood alone does not manage 350 people.
This article was originally published at 3 a.m.