Women in Silicon Valley Tech: An Interview with Heidi Roizen and Will Marshall

One of Planet’s key tenets of diversity and inclusion is the idea of “leading from the top.” In practice, that means our executive leadership and Board of Directors leverages expertise from a variety of perspectives. When it came to adding a new perspective to Planet’s Board of Directors, we didn’t have to look much further than Heidi Roizen, investment partner at DFJ, who recently joined the Board.

Heidi is a powerhouse investor, entrepreneur, and corporate executive who has worked in Silicon Valley for over three decades. She co-founded the software company T/Maker and served as its CEO until its acquisition by Deluxe Corporation. After serving as VP of Worldwide Developer Relations at Apple, she became a venture capitalist, and is now an investment partner at DFJ.

We spoke with Heidi and Planet’s co-founder and CEO Will Marshall to get their take on gender parity in the Valley, and what tech needs to do to be more inclusive for women.

As a woman in venture, what’s your perspective on Silicon Valley and issues of gender bias since you started your career?

Heidi: I could probably write a book about the topic! We have a very long way to go until we have true gender ‘blindness,’ in which people don’t consider gender, consciously or subconsciously, when it comes to raising capital. But I also believe we are making progress from the days when I started. I raised my first round of capital in 1989, when most of the VCs I met with had likely not seen a woman CEO pitching them in who knows how long. It is probably no surprise that I ended up raising that round from another fabulous, legendary woman VC Ann Winblad. I raised my second round while I was visibly pregnant. I think the only thing rarer than a woman CEO was a pregnant CEO! I raised this round successfully from Tim Draper and John Fisher, which explains in part why I ultimately chose DFJ as the place to continue my own career as a VC.

As a male entrepreneur, what’s been your experience fundraising in Silicon Valley?

Will: Planet has been fortunate to fundraise capital in multiple rounds from great investors. When I reflect on this experience it makes me realize that as a man, had I been a woman with the exact same vision, skills, and business plan, Planet would not have raised as successfully. While I agree with Heidi that it’s getting better, this statement is pretty damning, so we’ve still a long way to go!

How are the cards stacked against women entrepreneurs? 

Will: Raising capital in Silicon Valley requires forceful behavior that is seen as confident when done by a man and aggressive when done by a woman. Men are rewarded for brazen fearlessness and self-confidence and a quickness to argue, interrupt, and question others for the sake of pushing an idea. Women are punished for similar behavior. Once funded (usually on worse terms) women entrepreneurs often get treated worse. Partners micro-manage them, yell at them, and mansplain things to them. They aren’t trusted nor empowered to do their jobs.

Heidi: I’m the poster child of subtle gender bias, which has been both surprising and depressing to me. I have been called aggressive and bossy, but also deemed a great leader, empathetic, and yes, even funny – which I think is a great leadership attribute. The women entrepreneurs from my generation are all very thick-skinned survivors, which is what we had to be to make it.

What’s at the crux of the issue?

Heidi: There are so many contributing factors, including the predominance of men in undergraduate and graduate technology programs; the predominance of men in venture capital; and even simply cultural heritage. It is a terribly difficult battle when there is so much stacked against women. However, the more women we see become successful in technology companies, and the more women who become investors, the more these issues will move to the background. I can say from personal experience at DFJ with multiple women on the investment team, when our team collaboratively looks at a deal, gender is not an issue.

Will: These are deeply ingrained cultural and institutional biases. In many cases, sexism is totally unintentional. Venture firms and partners largely don’t go to work thinking ‘How can we screw over women?’ These issues grew out of institutions and processes that for historical reasons privileged the white male entrepreneur, which are unconsciously carried out by women and men alike. As Heidi says, the more women who are brought in and rise up (in the case of VCs, to full decision-making partners) the better the system becomes – it’s just slow societal progress.

How do you find women entrepreneurs, and make it clear that capital is available for all entrepreneurs with great ideas?

Heidi: I always say “think globally, act locally,” which to me means giving women entrepreneurs an audience or at least some feedback or advice about their proposals. I am hopeful that because I and my fellow investment professionals at DFJ are very active in entrepreneurial circles where women entrepreneurs work (for example, the tremendous work my partner Emily Melton is doing with AllRaise), we are making sure they hear that DFJ is open for business with women entrepreneurs.

Do the issues facing women entrepreneurs mirror the challenges facing women in venture – and if not, how are they different?

Heidi: In many ways they are the same, we are very much in the minority and so face the typical issues. However, it seems an even tougher nut to crack in venture, because having been a successful entrepreneur, senior tech executive or super-angel investor is a prerequisite for most if not all VC partner roles, so there are even more hurdles.

What needs to be done to improve the venture ecosystem for women?

Heidi: We just need to keep inviting women in the door. We also need to educate women entrepreneurs about venture capital – how it works and what kind of companies it is best suited for in terms of funding. I highly recommend the book by Brad Feld and Jason Mendelson on the nuts and bolts of venture capital. Entrepreneurs regardless of gender should understand the VC business if they intend to seek funding from VCs.

Will: Our experiences at Planet make me pretty upbeat that things can be done. Firstly, venture firms need to take action to diversify so that women are represented in the decision-making partnership level. It’s heartening to see more efforts toward this. Secondly, there needs to be more unconscious bias training that is repeated over and over, as we are dealing with deep-seated sexism that won’t change overnight. Thirdly, the structure of day-to-day interactions, for eg, pitch meetings and presentations, need to change to accommodate ways of communicating beyond 10:1 grillings.

What steps have you taken to make Planet more equitable for women?

Will: A few years ago, I wanted to increase diversity on Planet’s executive team and board, with an initial focus on gender. To start, we began actively seeking women executives and board applicants to apply to these posts. With Heidi joining Planet’s Board, we now have a 4:2 men-to-women ratio on Planet’s Board and our executive team is 5:3. The women on these teams meritocratically fit the task, but they also signal that the organization supports and empowers women, which has an important cascading effect.

More broadly, our People team has been hyper-focused on bringing on more women in technical roles and in leadership. We also created an entirely new role, the People Partner for Diversity & Inclusion, to make sure our ambitions were operationalized. I’m happy to say that we have accelerated our rate of hiring women in technical positions to more than 30 percent. However, we have much more work to be done in the years ahead as we work to close the gap.