The One Thing Every Person Can Do To Support More Women in Enterprise Technology: #HacktheNetwork

Jessica Lin
Dec 1, 2016 · 7 min read

When we first embarked on this piece, we had an ambitious plan in mind.

This post was to tackle the challenge of women in enterprise technology — specifically, the low numbers of women we were seeing working at enterprise technology companies: at our portfolio companies, members in our workspace, attendees at our events, and the teams of startups and corporations with whom we work, most of whom are resoundingly male.

We face many challenges in enterprise technology: deep technical specialization, long enterprise sales cycles, the “uncool factor” we often face vs. our consumer tech cousins. But in my eyes, one of the biggest challenges (whether you consider it causation or correlation) is this underrepresentation of women in enterprise tech.

As an Asian-American female co-founder and General Partner at Work-Bench, an enterprise tech venture fund in NYC, I at times feel personally discouraged, staring ahead at what looks to be a truly entrenched and systemic diversity gap. It feels like this massive mountain can only be moved if we tackle all of the issues at hand: improving STEM education, holding unconscious bias trainings, ensuring diverse interviewer panels, implementing blind resume reviews, and so much more.

Research has shown that team diversity (and specifically, higher levels of gender inclusion) leads to greater financial returns. But I also know firsthand, from working alongside our companies day in and out that bridging this gender gap is much easier said than done. I have yet to meet a CEO who is not actively trying to diversify his or her teams, and many smart people have written extensively on all the ways you and your companies can tackle diversity:

We began addressing this diversity gap head-on earlier this year with our Women in Enterprise Series, a monthly forum of women in our enterprise community to discuss our best practices and biggest challenges, and where we host bad-ass female senior leaders in enterprise tech to share their pathways and career trajectories. In 2017, we have plans to do even more — across curated dinners and our first-ever Women in Enterprise Tech Summit, all of which we believe will be key to continue supporting and developing women already in enterprise tech.

But as I dug in further and spoke with many very smart men and women on this issue, I realized there was one specific area that we at Work-Bench could play the most impactful role.

And that is: leverage our network.

Why Our Network?

In meeting with many successful women in enterprise technology and asking “How did you get to where you are today?” — the same answer kept coming up, time and again: “My mentor helped me land this role at this company. My mentor coached me on that. My mentor has helped me tremendously in my career.”

These responses validate the research that shows good sponsors can supercharge a woman’s career by providing access to essential networks, bringing achievements to the attention of senior-level executives, and recommending her for key assignments, and support the anecdotal evidence that there is one thing every successful person has in common: a mentor.

One of the key parts of our model we are most proud of here at Work-Bench is our community and our network. As a venture fund and community, we have built a home and hub for enterprise technology here in NYC, across our 18 portfolio companies, 200+ events, and 15,000 subscribers to our weekly newsletter. In fact, our community helped us source 6 out of our last 8 deals, underscoring just how critical our community machine is to our investment model.

But there is a downside to this very same network — and that is as networks grow, it may create an (unintentional) adverse funnel effect that makes it harder for others to break in.

This is perhaps most pronounced in startups, who by their very nature are scrappy and fast-moving, and who in the early days, hire people within a founder’s network, with the unintentional consequence of the network becoming more homogenous over time.

As Backchannel recently detailed, about Meetup’s leadership transformation:

This is a familiar issue for many companies, but it’s particularly acute at tech startups, where technical skills are prized and speed is paramount. They’re started by founders who, in the push to assemble capable and comparable staff, hire people they know — often people who look like them. By the time founders are on steady ground and ready to think about building a diverse leadership team, they’ve already cemented a culture of sameness.

…The result is a paucity of women and people of color in companies’ senior ranks. Only 18 percent of the top management positions, or c-level positions, at companies are held by women, according to McKinsey’s 2016 Women in the Workplace Report. Women of color only hold three percent of those senior positions.

This network compounds over time, with successful companies. If your first company was successful, you likely hired from your circle of friends or acquaintances from your previous company. At your next company, you’ll bring on similar folks, and so forth, with it being hard for an “outsider” to become a part of your network.

The problem is not skill or capability. There are enough women who can be hugely successful in enterprise tech. The problem is that it may be hard for women to access traditional enterprise tech networks, ultimately making it difficult to find and hire them.

The irony is that I’ve heard from countless women in our community just how hard it is for many of them to find a mentor, underlining not only the genuine demand for mentors, but further supporting our hypothesis that additional frameworks may be needed to support women and other diverse groups who may not have defined paths to access these established networks.

What we are proposing is #HacktheNetwork: an initiative which leverages our own powerful network as a force multiplier to help us expand our reach to bring more women and diverse groups into enterprise technology.


  1. Sign up by answering 6 quick questions
  2. Get matched with a mentor/mentee by field or function by Work-Bench, across our NYC enterprise tech community (at least one person in your pair will be engaged in enterprise tech)
  3. Set up a recurring bi-monthly calendar invite to meet for coffee, across 2 quarters
  4. Report back in a survey to help us track data

We encourage everyone — men and women of all ages, experience levels, and most importantly whether you are currently in enterprise tech or not — to sign up.

Why You?

So why should you sign up for #HacktheNetwork?

For Mentors

If you have ever had an influential mentor shape your career and life, then this call to action is for you: pay it forward.

One of my favorite quotes: “When you’ve walked through that door of opportunity, you do not slam it shut behind you. You reach back and you give other folks the same chances that helped you succeed.”

Join our impressive group of mentors, advisors, and executives from some of the leading enterprise technology companies here in NYC.

For Mentees

And for you as a mentee — I’ve been in your shoes before.

I too have struggled to identify leading women in enterprise tech VC to shadow, follow, and sponge up knowledge. It can be a lonely experience and one that I have had to put a lot of effort into, to navigate.

It is from my own personal experiences why I am so passionate about launching an initiative like #HacktheNetwork, and why this is my call to you. We know that this is still an ambitious plan, and we know that critical to strong mentor/mentee relationships are 1. the matching needs to be thoughtful and 2. that the mentor needs to truly care and be invested in the mentee’s success.

With that said, we’re also confident that a community of people who are willing to learn, share, and — yes, hack — to create a new kind of network is very much forward movement to tackling our enterprise gender gap mountain.

Stay tuned for our next blog post, where we look forward to sharing our early data and results from #HacktheNetwork.

Sign up for our Enterprise Weekly newsletter to get involved with our Women in Enterprise Tech series, across our lunches, workshops, dinners, and more.

Thank you Laurel Woerner for all of your mindshare and muscle on this piece.

And of course, a big thank you to my own mentors Ruth Brown, Joyce Shen, Anne Libby, Michael Balaoing, Vanessa Liu, and so many more for their continued encouragement and wisdom — I am so grateful.

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