Kristen Hamilton at Startupday 2015
Seattle entrepreneur Kristen Hamilton at GeekWire Startup Day 2015. (GeekWire File Photo)

Editor’s note: Kristen Hamilton is a Seattle entrepreneur and investor who co-founded Koru and Onvia, helping to lead the latter company to an initial public offering in 2000. She wrote this commentary in response to GeekWire’s inquiry and story about the lack of women leading companies to IPOs. 

The short answer I have about why so few women are leading companies through IPOs is that the game that needs to be played to get there has been designed, defined, and largely played by men (white men in particular).

For a woman to succeed in the upper echelons, there are myriad challenges. For women who were the real pioneers, who helped pave the path for me and my sisterhood, I think there was only one way: be as much like a man as possible.

Because of the heroic work those women did, our generation of female leaders has a slightly better set of options: we can try some adapted versions of be-like-a-man, we can find a wedge into being accepted as one of the boys (e.g. I really do love extreme sports), or stand firmly as who we are, taking a different approach to some or even most things, and hope to find allies among peer CEO/founders.

My personal journey has been to try all three of these over time.

In 2000, we filed for Onvia to go public. I co-founded the company with my dear friend Glenn Ballman. I see us as having been equal partners — he wanted to start an e-commerce business, and I told him if we focused it on small business and based it in Seattle (we would not have raised the money in Canada in those days), I was in. We both were in every fundraising meeting for the company, including the IPO roadshow. I brought in our board chair and hired a lot of the best leaders we had (like Clayton Lewis).

Our board, led by Nancy Schoendorf, one of the best VCs in Silicon Valley at that time, made clear that I needed to be on the roadshow along with Glenn and our CFO. I also stayed at Onvia post-IPO for longer than Glenn did, to lead the work to reposition the company after the dot-com crash.

All this to say — it was an unusual situation and I believe I deserve equal credit with Glenn for leading that company from start through IPO. Lots of people still in Seattle were on the inside to see it happen.

Back in the Onvia days we were so far from any kind of Me Too movement that I remember only one woman I talked to about the boys club we lived in, and that was in a late night conversation with Heidi Messer at one of the boondoggle weekend long parties that VCs threw back then.

We were calling it a night because the party was such a sausage fest. My approach then was to keep my head down and focus on the work.

I refused to acknowledge a glass ceiling. Talking about one only gave it legitimacy in my mind.

I realized over time that this may have worked for me, but it did not serve to improve things in general or for others. The 15 years between starting Onvia and Koru included two stints at Microsoft and being COO of a global NGO. I no longer had the luxury of keeping my head down and focusing on the work. Workplace politics, bias and injustices made we wiser and also occasionally wanting to go back to working on a horse farm or mountain guide!

I resisted becoming a CEO both back in the Onvia days when our CFO specifically suggested I should take on the role after Glenn, and when I was brainstorming with WTIA CEO Michael Schutzler about ideas for a subsequent new company.

He finally told me: “Nobody ever feels ready to be a CEO. You’re ready!”

I resisted because I knew the game and how hard it would be to succeed at it. I did it though, and it was an unparalleled journey of growth, and pain.

What I’ve learned, and the simple advice I’d share with other women CEOs is that to be my best leader, I must always be my most authentic self.

Easier said than done.

After years of trying on personas that I thought those with power wanted, I lost myself. It took real work (and help from coaches and my co-founder Josh Jarrett at Koru, and the Leaders In Tech program) to rediscover and reconnect with my core self and then learn to lead from that place.

I’ve learned that it’s a massive advantage to be a woman leading as a woman, with the confidence borne of experience, and the friendship and support of so many (mostly male still) other founders who’ve been through a similar experience. I notice more of those male peers leaning in to listen now when I speak my truth.

So now I’m feeling actualized as a leader yet alas, I’m still not sitting atop or on the board of a public company. Why?

Well, despite the things I’ve done and objective facts that say I’m qualified, it’s still a numbers game. And the numbers are not stacked in our favor as women.

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