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Tech Women Choose Possibility

An open letter of encouragement from an entrepreneurial woman in Silicon Valley.

When I came to Silicon Valley 18 years ago, I stayed.

I found the place that fanned the flames of my ambition and my irrational faith in what I could achieve. I went on to lead large businesses at Google, and to found two companies — Yodlee and Joyus — and have been fortunate to work with a handful of others as board member, adviser or investor (TripAdvisor, Ericsson, Twitter, Stitch Fix among them). I am one of thousands of women entrepreneurs who have found success and fulfillment here in the last 20 years.

But before I stayed, I almost left. Having arrived here with a successful track record in media and investment banking, I was surprised to be told by my first tech boss that I “scared the secretaries” on my second day at work. After being given increasingly junior tasks and watching a volatile male colleague’s behavior get rewarded, I considered leaving the Valley altogether. Instead, I switched jobs, moving to a startup where the four (male) founders embraced my drive, and found my way.

More universally, all tech entrepreneurs, not just female ones, encounter bias. Be it gender, age or business model, people make judgments about us as we pitch our vision long before we have data. Beyond biases, we face mixed data signals every day as we keep iterating between vision and reality over months and years. Were we to yield to stats or all the negative signaling, no one would ever start a company. But as a startup community, our most universal bias is toward possibility.

The missing perspective on women in tech

Over the last few months, press coverage about women in tech has been dominated by the “negative” signals. The narrative rightly identifies many of the issues in the Valley that demonstrate women are not yet contributing at their fullest potential here.

But absent almost entirely in this coverage is the experience of women entrepreneurs themselves. Looking at the press, one might think women entrepreneurs are not only hard to find, but struggling to succeed. If we want to progress the path of potential women founders, it is equally important to bring this perspective to the table.

The story of women tech entrepreneurs goes far beyond bias

I reached out to about 100 women tech entrepreneurs across the country and asked for their help in shaping this perspective. Through a simple survey, coupled with public data collection, a picture starts to emerge of some of the women who are and have been building tech companies successfully in the Valley for the last 20 years. To see the full list, or to add your own data as a female founder or growth CEO, please click here.

First, the number of women starting tech companies is rising in absolute (if not yet relative) numbers. To illustrate what’s possible, we’ve highlighted a cross section of 230 women on this list who have collectively started or led 298 tech companies across all sectors and stages of growth over this period. Approximately 29 percent of women on this list are serial entrepreneurs.

The women on this list founded heavyweights such as, Nextdoor, Houzz, VMware, ASK Group and Mozilla; growth-stage stars like Stitch Fix, Slideshare, Indiegogo, LearnVest and StyleSeat; and earlier-stage startups like Lumoid, Heartwork, Other Machine Company and Trendalytics. On this list alone, we were able to identify 13 IPOs and another 54 exits through M&A. The average amount of capital raised per company is approximately $34 million (for a subset of 167 companies on which data was available).

Through the survey, we are able to identify some other notable trends in our paths as women toward tech entrepreneurship:

  • While we acknowledge the importance of STEM, it is very possible for women who do not hail from STEM to start tech. Some 16 percent of our respondents came from STEM undergraduate programs, while 84 percent did not. Of those with graduate degrees, most common degrees were MBAs, with 13 percent hailing from STEM disciplines.
  • The “entrepreneur gene” seems to run in our families, also. About 54 percent of us are the children of entrepreneurs, and from an early age were exposed to the concept of owning our own business.
  • While both parents served almost equally as role models, our fathers’ vocation was more often associated with professions like “entrepreneurship,” “CEO,” and “engineering” than our mothers’. The most cited profession among our moms was “teacher.”
  • Men have played an important role as professional mentors for most of us. Some 37 percent of us would cite our biggest professional mentor as male, while 16 percent would cite women, and 47 percent would credit both genders equally.
  • Women venture capitalists appear to be disproportionate supporters of female entrepreneurs. While women make up approximately 3 percent to 6 percent of the VC community, 30 percent of our first checks came from women investors, with 15 percent being from a woman investor alone, and 15 percent investing alongside the first man.
  • Almost half of us — 43 percent — have had children while running our companies, though it’s less the case that we founded our company with children already (only 32 percent).
  • About 86 percent agree that women are judged differently than men, with the most common issues cited around perceptions of our “aggressiveness” against expectations of “likeability,” and general unconscious bias within our culture.
  • A full 67 percent of us can cite a memorable incident of perceived bias in the workplace, and 65 percent in the fundraising process. Sexual harassment is less prevalent, but still very much alive as an issue. More than 35 percent of us can recount a specific incident in our career. Anecdotally, we saw a greater number of comments about bias and harassment in the fundraising process itself.
  • Tenacity/Resilience, Drive/Passion and Work Ethic rank among the Top 3 traits cited by this group as most attributing to our success.
  • An overwhelming majority of us would recommend entrepreneurship for our daughters (84 percent), and those who weren’t sure (16 percent) identified that “entrepreneurship” is not suited to everyone as a career choice.

We have not been exempt from gender bias or worse in our careers; it has simply not been the defining factor in our journey as entrepreneurs. Like all entrepreneurs, multiple other forces have influenced our ability to build our own companies.

Overall, if this cross-section of women entrepreneurs in any way represents the larger whole, we are the biggest “bulls” on women starting tech companies today.

Iterating faster toward possibility

At the same time, every part of the startup ecosystem has the opportunity to increase the rate of progress for women in tech entrepreneurship. Some ideas will succeed, others will fail, but we know that iteration matters in building momentum behind any large vision. Here’s what it might look like:

  • Entrepreneurs seeking to enhance their startup’s performance can choose today to add their first qualified female board member or investor. Diverse thinking can benefit private tech boards potentially even more than public ones, and there is no reason to wait.
  • Startups seeking to attract women could choose today to create best practices in the areas of family planning and leave policies early and proactively. We can make this as easily understood as cap tables and free lunch programs among first-time founders.
  • Venture capitalists (and their LPs) looking to understand their own biases and also their progress could choose today to track female versus male stats (pitched to funded) in their deal pipeline, and even publish it proactively.
  • Venture capitalists seeking to attract the best entrepreneurs could choose today to be explicit in their term sheets on their own zero-tolerance policies for sexual harassment and other discrimination, as well as demanding the same of their portfolio companies. This is a simple signal, and it goes a long way to both genders of top-tier entrepreneurs.
  • Investors and board members looking to grow the best companies can choose today to vigilantly treat female founders and CEOs with the same level of candor, directness, expectation and measurement that they would any other CEO or founder, rather than operating from a latent fear of “female emotion.”
  • Women who are starting or working in a tech company can choose today to oversell their vision rather than underselling themselves, as they are competing for resources and mindshare with people who pitch big ideas.

As we execute in big ways and small, we also signal our intent. And in the world of tech, all signals are not created equal. It’s time to show potential female founders even more clearly that we #ChoosePossibility.

Special thanks to Keval Desai, a partner at InterWest, who encouraged me to write this letter, and whose portfolio is more than 50 percent female.

Sukhinder Singh Cassidy is founder and chairman of Joyus. Before starting Joyus in January 2011, she spent almost 20 years as a leading consumer Internet and media executive at global and early-stage companies including Google, Amazon, Polyvore, Yodlee and News Corp. She currently serves on the boards of TripAdvisor and Ericsson, and has previously served as an adviser to Twitter, on the Advisory Council for Princeton University’s Department of Computer Science, and as a board member of J. Crew Group. Reach her @sukhindersingh.


Alexandra Wilkis Wilson | Gilt
Alison Pincus | One Kings Lane
Allison Johnson | West
Amy Chang | Accompani
Anna Santeramo | StyleBee
Barrie Seidenberg | Viator*
Brandee Barker | Pramana Collective
Caroline Ghosn | Levo League
Clara Shih | Hearsay Social
Dana Loberg | Movielala; Art Debutante
Darlene Mann | Akoonu
Dawn Lepore |*
Debbie Sterling | Goldieblox
Diana Williams | Joyus
Donna Dubinsky | Numenta; Handspring; Palm
Eloise Bune | Gracious Eloise
Gisel Kordestani | Crowdpac
Heidi Roizen | T/Maker
Heidi Zak | Thirdlove
Jana Rich | Rich Talent Group
Jennifer Fonstad | Aspect Ventures
Jennifer Sharp | HDGreetings
Jessica Lee | Modern Citizen
Joanna Drake Earl | CurrentTV
Julie Sygiel | Dear Kate
Karen Moon | Trendalytics
Katina Mountanos | Manicube
Katrina Lake | StitchFix
Kirsten Green | Forerunner Ventures
Laney Whitcanack | BigTent
Leah Busque | TaskRabbit
Lisa Stone | BlogHer
Liz Whitman | Manicube; Lewis Albert
Lorna Borenstein | Grokker
Lynn Jurich | Sunrun
Maria Seidman | Yapp
Mariah Chase | Eloquii; Send The Trend
Mauria Finley | Citrus Lane
Melody McCloskey | StyleSeat
Mila Krivoruchko | Milasya
Rashmi Sinha | SlideShare
Ruzwana Bashir | Peek
Sandra Kurtzig | Kenandy; The ASK Group; Ebenefits
Sandra Lin | Kiwi Crate
Sheila Lirio Marcelo |
Shaherose Charania | Women 2.0
Shanna Tellerman | Pencil and Pixel; Sim Ops Studios
Sheri Atwood | SupportPay
Sonja Hoel Perkins | Broadway Angels
Stephanie Tilenius | Vida Health; Planet RX
Susan Feldman | One Kings Lane
Susan Gregg Koger | ModCloth
Susan Lyne | Gilt Group
Theresia Gouw | Aspect Ventures
Tina Fitch | Hobnob, SwitchFloy
Tina Sharkey | Sherpa Foundry*; iVillage
Tracy DiNunzio | Tradesy
Tracy Sun | Poshmark

* Non-founder CEO

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