At the few tech companies led by female CTOs, ‘brilliant jerks’ are not allowed

When Cathy Polinsky enters a room, she does “the count.”

A software engineer who worked at Amazon, Salesforce, Oracle and Yahoo, Polinsky has grown accustomed to being one of a few — if not the only — woman in a meeting. Now, she finds herself unconsciously noting when another woman joins her.

“I remember early on in my career being at the kickoff meeting for a big new initiative,” she said. “There were 50 people from the business, product and engineering sides of the business, and I was the only woman.”

Recently hired as the CTO of subscription clothing service Stitch Fix, Polinsky is committed to creating a culture for female software engineers that is different than what she experienced when she was starting out. More than 30 percent of Stitch Fix’s engineers are female, and Polinksy attributes their ability to attract and retain female talent to the startup’s core values. Similar to many other high-growth companies in Silicon Valley, San Francisco-based Stitch Fix looks for people who are “bright” and “goal-oriented.” But it’s the third core value that Polinsky believes makes the six-year-old startup with more than 5,500 employees stand out: You also have to be “kind,” she said. 

The subtext? No “brilliant jerks” allowed.

“If someone came across as not having these qualities, we would not hire them,” she said. “We talk about it every day. It is not something that we just say once and ignore.”

Polinsky is a part of a small — but growing — group of female CTOs at tech companies. Only 5 percent of CTOs are female, the least common executive-level job title for women. While CTO remains the least common executive-level job title for women, there has been a 60 percent increase in female CTOs since 2008. As Uber reels in the aftermath of a sexual harassment scandal that paints the company as largely inhospitable to female talent, Polinsky and her female CTO peers are on high alert to ensure their companies remain inclusive to diverse talent. For most, that starts with overemphasizing team values like teamwork and empathy that make the environment at work more welcoming for women.

When asked to describe her team, Redfin CTO Bridget Frey uses words like “nice,” “friendly” and “collaborative.” While she was the only female engineer working out of the Seattle office when she joined the online real estate broker in 2011, now 30 percent of the engineers on her team are women. At one point when the company was ordering new T-shirts, a female engineer pointed out that only men’s sizes were available to order. Frey encouraged the engineer to reach out to the manager ordering the T-shirts to make female sizes available as well.

It’s small problems like these, Frey says, that she is constantly looking out for before they turn into larger issues.

“You really have to make sure that you have a dialogue going at your company and hearing about problems,” she said. “If you are not hearing about the small problems, you definitely won’t hear about the big problems.”

Liz Crawford was the first CTO at subscription beauty service Birchbox and watched the company grow from roughly 10 employees to more than 250. When you are at the company that early, you have the luxury of creating the culture you want from the start, Crawford said. For her, she always looked for engineers who enjoyed working as a team to solve problems.

The recruiting practices that Crawford and her peers preach may sound good in theory, but can be difficult in practice. For every one web developer or engineer looking for working in the U.S., there are roughly five open positions creating talent crunch for growing companies. That said, Crawford and others were unwavering in their commitment to keeping bad actors out to ensure their companies stay “stable” or “well rounded” as they scale.

“High-performing individuals should not come at the cost of having high-performing teams,” she said. “If we interviewed someone who was a brilliant as*hole, we would not hire them. That makes a difference.”

While the efforts of Crawford and others are a solid start, the ascension of female tech talent to the CTO role remains almost accidental. For Frey and Polinsky, they attribute their love for computing to happenchance circumstances that gave them access in elementary school to Apple II computers. Similarly Susie Wee — the CTO of DevNet Innovations at Cisco Systems — remembers her father, a medical doctor, bringing home a computer when she was young. This gave her the opportunity to learn how to code. This access and opportunity are what makes all the difference. When asked why there are so few women in CTO roles today, most of the CTOs I interviewed acknowledged that the pipeline just isn’t built out yet. Wee’s team of direct reports is predominantly female, but she still wishes there were more women going into technical management.

Kimber Lockhart might have dropped out of computer science while at Stanford University if it weren’t for one professor who told her she had a knack for coding. Now the CTO of healthcare startup OneMedical, Lockhart said that it was “a small realization over time” that she was interested in pursuing a technical career. Roughly 50 percent of her engineering team is female, but Lockhart said she still has trouble finding diverse talent to bring in the door.

“The pipeline is getting stronger, but the data tells us that many fewer women get into engineering leadership roles,” she said. “We might be small in numbers, but we are outsized in influence.”

Female hires account for roughly 28 percent of overall technology industry hires in 2016, up from 23 percent in 2008, according to LinkedIn data. To make technical leadership roles more relatable for women in her organization, Intuit’s Raji Arasu works diligently to openly share stories of failure. If Intuit doesn’t have diverse members driving product decisions, the company won’t be able to build great products, she said. “I don’t think we compromise on capability, but we certainly don’t compromise on culture fit either,” she said. While companies like Uber are just starting to come to this realization, Arasu said industry leaders like Intuit need to set an example for others to follow.

Still just three months into the job, Stitch Fix’s Polinsky has high hopes for the change she hopes to create both inside and outside her company. Similar to how she has grown accustomed to being one of just a few women in the room, she has also gotten used to answering questions about what it’s like to be a female tech leader. As more women fill the technical workforce pipeline and rise in the ranks at companies in Silicon Valley and beyond, Polinsky says she can imagine a world where gender plays a much smaller role in the equation.

“I just want to be seen as a great technical leader who happens to be a woman,” Polinsky said. “Five years from now, I hope this is less of a story about me being a woman CTO and that I’m just the CTO.”

[Photo Credit (Top Right to Bottom Left): One Medical CTO Kimber Lockhart, Sr VP, Platform and Core Services and CTO Dev at Intuit Raji Arasu, Stitch Fix CTO Cathy Polinksky, VP and CTO of DevNet Innovations at Cisco Systems Susie Wee, Redfin CTO Bridget Frey and Former Birchbox CTO Liz Crawford]

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