Apr 25, 2017 ยท 9 minutes

Sukhinder Singh Cassidy is not one of those people who has a Silicon Valley horror story of sexual assault, domestic violence, or sexual harassment.

Instead her experience has been one common to a lot of women I know here (including me): A ton of unconscious bias and plenty of having to prove herself in situations where men might not have to. And yet, she’s also been given a lot of opportunity by men who did believe in her. Her ecommerce company, Joyus, has raised nearly $70 million in capital from top industry names, for one thing.

“A very important thing here is to acknowledge the duality,” she says. “Personally the Valley has been good for me, but at a macro level it’s not so great for women. Both of those are true.”

It’s women like Singh Cassidy that have created a huge shift in how women think about and talk about gender in Silicon Valley in recent years. Women who, for a long time, didn’t believe sexism was a pervasive problem here or didn’t want to openly acknowledge it. Women who chafed at the idea of being written up in a feature on top women in tech, because they felt being written about as a female CEO or a female entrepreneur would diminish  their accomplishments. Women who believed that they were doing enough to advance the position of women in the Valley by simply existing. By simply succeeding. By being a positive data point. “Everyone was talking about women in tech except the women in tech,” she says.

This has been an ongoing theme on my podcast about motherhood and entrepreneurship. Julie Hanna talked about how her comfort in being “one of the guys” for so much of her career, made her blind to the sexism in the industry for a long time. “I remember I had a boss and a mentor in my 20s, and he was an older gentleman,” she told me on the podcast. “And he said to me, ‘You have to understand when you walk into a room the first thing guys will see is ‘babe.’ And then you start talking and eventually they see beyond that, but that’s the natural reflex.’ And I would argue and fight with him. I would say, ‘No, no, no, the world has changed.’ I had a strong belief he was wrong. Now, I think it was more true than not, and I just wasn’t aware of it.”

Michelle Zatlyn, co-founder of CloudFlare, similarly summed up this duality when she told the story of a VC who said-- to her face-- that women didn’t belong at infrastructure companies. And yet, she shook that off and raised nearly $200 million from others who didn’t feel that way. “Just know, it’s not everyone,” she said to young women who might have been listening to that episode. “Associate yourself with people who do make you feel good, and want you to win because there is someone out there who will bet on you.”

Before Ellen Pao came forward and declared micro-aggressions and unconscious bias as something that was lawsuit worthy, a lot of women who’d faced a career of unremarkable sexism in the Valley felt it was just part of the bargain you had to accept. Is it OK to be pissed at one VC making a slight like the one Zatlyn heard if another $200 million in capital did take a risk on you despite your gender?

Maybe it’s age, maybe it’s ripples from Pao, maybe it was the conversation that started when Sheryl Sandberg did stand up and identify herself as a female executive in writing “LeanIn.” Maybe it’s the bro economy, maybe it’s reports of much more aggressive sexual harassment and even violence against women coming out in tech. Maybe it’s the Trump Administration too. Whatever it is, women in the prime of their career are increasingly having an about face on what your responsibility is when you are part of that 3% of women CEOs who’ve raised venture capital.

Singh Cassidy’s realization that simply being a woman in tech wasn’t enough to change things came a few years ago.  The move came out of conversations she had with VCs about the persistent gender imbalance in the Valley.

They’d talk up investments in STEM education, and Singh Cassidy would point out that there are plenty of CEOs, senior execs, VCs, and board members who aren’t engineers. She pointed out that you could impact 100% of startups in the Valley today by focusing in on the boards. VCs would tell her that some industry-wide push to do this was a great idea, but ultimately they were just going to focus on their own firm. “The conversations went nowhere,” she says. “In the second quarter of 2016, there was yet another cover story on how terrible it is for women in tech. On the one hand I agree, but it’s also been a great place for me.”

She started The Boardlist, a company that collects peer-nominated profiles of women that are absolutely qualified to be on boards. It launched publicly about a year ago, and  Since then, companies have opened 250 searches on the Boardlist, and about 1600 women have been nominated by a community of some 1000 “endorsing members” that include CEOs, senior execs and VCs. She believes the Boardlist has “influenced” some 61 placements, although it can be hard to track.  

In its first quarter report, released today, The Boardlist says that 24 open tech company board seats were filled by women, eight of whom were featured on their site. The range has been between seven and 23 a quarter. “There is no doubt we are trending upward,” she says. In particular, unicorns are making progress, she says. When they first started tracking the class 38% of unicorns had one woman on their board, and now 45% do, she says.

I asked if the 20-something Singh Cassidy would have ever imagined herself building something so…. well, feminist. “Even the 40-year-old me would be surprised I’m doing it,” she says. “Like everyone, my first goal has been to build a career of impact as a leader, not a female leader or a female entrepreneur, just a leader full stop. I don’t think this was something I was even attuned to. I am totally shocked that this is something I pursued. That narrative on women in tech that started after LeanIn, just continued. At some point, I realized I had a lot to say and I was just sitting on the sidelines. Why am I afraid to say something? That people will perceive me as less if I talk about women’s issues?”

Clearly, she got over it. She’s even becoming a believer that the government needs to do more to hold companies accountable. She’s not quite to the point of embracing quotas, but is swayed by the approach of governments like the UK and Australia where governments have “comply or explain” pressure on companies to add more diversity to boards. “Quota is a pretty scary word,” she says. “‘Comply and explain’ is a step before that, where you have the threat of the penalty versus the actual penalty. We need some level of accountability.”

And her year-plus of building the Boardlist has only deepened her conviction of the importance of women filling more of the Valley’s empty board seats. Research has shown that when women join boards, companies do better at promoting senior executives, which has a trickle down effect throughout the company.

It’s slow-going, increasingly manual work. Before you even get into the whole gender thing, it’s a hurdle to convince entrepreneurs to even fill independent board seats at all. A lot of this stems from the Valley’s current obsession over founder control. “They think filling the independent board seat is a risk, but I think it’s a risk mitigator. For one thing, you are able to rent the talent you can’t buy. We have to do a lot of education and evangelism,” she says. “Constant evangelism.”

And despite being senior tech folks, her users are resistant to using automated tools. “They all have log-ins and it takes less than a second, but they still want to send me a two-line text or email nominating someone instead,” she says. “It can’t be completely self-service.”

The Boardlist actively markets to companies who’ve just completed a fundraising, “The only time a CEO is actively thinking about their board,” she says. They’ve even recently hired someone to manually go through abandoned searches and follow up and try to help get them over the finish line. “You have to put a body on the problem, and make it a priority for someone or it will fall off the list,” she says. “An automated email isn’t going to do it.”

I spoke with Singh Cassidy this week from Canada, where she was celebrating The Boardlist’s launch there. She noted that the experience had convinced the company they actually had to expand slower internationally, not faster. “It’s been great to launch here, but it’s very clear that before we launch more countries we need a more robust online product,” she says. “We will probably slow expansion plans because I want to add functionality to the product. Each market requires not just online support but physical community management and content. We are going to spend the rest of the year improving that.”

In some ways, this is the perfect time for an organization like the Boardlist to exist. Tech’s diversity problem is only getting more highlighted everyday, and there’s new pressure to release diversity stats and actually do something about it. Plenty of men in the ecosystem are looking for ways they can have an impact, can do something tangible, and being a part of a group like Boardlist and surfacing more qualified women for boards is a relatively easy step.

And yet, plenty of research shows that almost no progress is being made on a macro level. Worse: Survey after survey is showing that 95% white men don’t prioritize the problem, only 25% of startups are even trying to do something about diversity, and 40% of white men are sick of hearing about it.

The whole argument that data would change things-- a central tenant of Sheryl Sandberg’s approach with Lean In-- mostly hasn’t worked either. We are awash in data about how gender diverse teams perform better, how much later the economy would be if more women worked, how women outperform as VCs and as entrepreneurs when it comes to certain metrics. And still, little changes on the macro level.

Singh Cassidy’s approach-- board seat by board seat-- may be a painfully slow and un-automated way to change the industry. But over time, it may have a greater impact than data and guilt.