Even as a Female CEO, Gender Diversity Isn’t a Given

When I first founded Chewse, I made an assumption that as a female CEO I would naturally attract more women executives and board members than most other companies. I was wrong.

And now, I feel as helpless as every male CEO who muddles through the same problem.

This is really personal. I believe not finding another female executive hurts the chances of my own success, because I want a female role model of success. Who has walked her path and thrived.

In some ways, building a company as a woman has helped. We’ve oriented our company towards a truer meritocracy by instituting open, fair salaries. Our culture promotes emotional vulnerability as a good thing, not as a liability. Because of this, Chewse is outperforming the industry on gender diversity at most levels.

Sources: Grant Thornton Women in Business , Kapor Center Tech Leavers Study

As proud as I am of the gender diversity at Chewse, I recognize that there’s a gap I feel acutely. Outside of me, my board and VP/C level consists of all men. From my seat, that’s 0% female representation at the highest levels of the org.

We’re hiring for a VP Finance and I’m scared because we aren’t getting a lot of women applying for the role. What does this say about future executive roles that we hire? Why does this bother me so much?

I’m Looking to Be Understood in My Uniquely Female Company-Building Journey

I’ve been told that I’m not out for blood, that I’m not aggressive enough to be successful in such a tough industry. It makes my blood boil. And then I feel the dangerously close, all-consuming anger that threatens to take over. To pull me farther from my mission of building a company based on love.

But under the anger, really, I’m heartbroken. This is difficult to grasp until you are told that you are not enough. I’m fearful that I may never be accepted for who I am in an industry that I’m passionate about. That communicating in a way that’s authentic to me, by exuding confidence that’s natural to me — I’m never going to look the way the industry wants me to. And that I’ll never be successful.

I’ve practiced my fundraising pitch with male advisors who care deeply about my success. And their advice? I don’t sound confident enough. Even though I feel confident. My tone isn’t assertive enough, I don’t answer questions quickly enough, I don’t stare unflinchingly at the investor as I mentally give him the finger and tell him why he’s wrong.

Yeah, fundraising is weird.

Don’t get me wrong — I love working with men. Many of my greatest mentors and investors are men, and they are also my biggest cheerleaders. But I know how much easier the journey would be for me to have just one more woman at our board meetings and around the executive table. Who understands what confidence for me looks like, who gets it when I tell them I don’t want to be an asshole to raise a ton of capital and build a company of epic value. Who has been there, struggled through it, and has found a solution that suits her.

I want to see how other women navigate the waters of management, fundraising, persuasion, and vision-setting. Of balancing marriage, business, and family. How they inspire and lead.

There’s a fascinating Harvard Business Review study about why female entrepreneurs are more successful with female VC backers. My hunch is that it’s the same reason I want more women at the executive table — the entrepreneur wants the ability to look across the table and see a face that mirrors her own. To talk about what her female customers want and see another woman nodding along with her. To feel an innate connection based on one of her most important identifiers: gender. The value of that is immeasurable but tremendous.

It will certainly make the journey less lonely.

Join Me In A Commitment to Rising Female Leaders

Why are there so few women in leadership roles in tech? It’s a huge, complicated topic that no one has a clear answer to.

The one place we feel it acutely at Chewse is that the majority of applicants to our leadership roles are men. For our open VP Finance role, it’s a 6:1 male:female applicant ratio. The few women who do apply tend to not have held executive roles before, which creates a vicious cycle that women without previous executive experience aren’t given the chance to serve in executive roles.

Many women work in environments that don’t understand or care about providing support and rallying cries for them to rise into leadership roles. More subtly, their voices are quieted at meetings as they get talked over and the credit goes to the loudest person. That’s the message: you will be bulldozed until you scream. And if you don’t want to scream, well, you won’t get anywhere. That’s a difficult message to encourage when women are raised to be quiet and agreeable.

We need to systematically support aspiring female executives to give them tailored mentorship and access to networks that will lift them into these top roles.

That’s why I’m excited to unveil our Chewse Rising Leaders Program (application here). We want to help women get to the next stage in their careers. We’re calling on women everywhere who have not held a VP-level role before to apply for a Chewse mentor from our leadership team. You must be willing to commit to 1 hour a month either in person or on a phone call. You’ll be assigned a mentor for 6 months and you’ll spend the first session setting up specific outcomes for the program.

If you are a founder or executive at another company interested in kicking off your own external mentorship program, reach out to me at tracy@chewse.com — I’d love to include you in this round or future rounds.

If you are a VC backing a female founder, push to get another woman in the room as either an independent or an observer. It will level the playing field and improve the odds of you and the company having a successful outcome.

If there’s a time for women to rise up the ranks, it’s this very moment. It’s good for business, it’s good for softening the intense masculinity of tech and industries beyond, it’s good for employees. I look forward to see Chewse and other heart-forward companies experiment with new ways to open up the ranks to new, diverse opinions and people. To see the VC community more accurately evaluate diverse founders.

Until that day, I encourage women to rise up and embrace the feminine in all arenas of their leadership. Don’t be an asshole if you don’t want to be, use relationship-building to your advantage, and be authentic if you don’t know the answer. Prove that we can win, but we do it playing by our own rules.