Jessica Lin is at the intersection of two male-dominated industries — venture capital and enterprise technology. Lin is the cofounder and general partner of Work-Bench, a venture fund and community that identifies, supports and invests in the next generation of enterprise technology startups. Since founding Work-Bench in 2014, Lin and her cofounder have invested in 18 startups, created a bustling workspace in their New York City-based headquarters, and hosted a bevy of community events. Lin is passionate about closing the diversity gap in enterprise technology. After realizing that it’s difficult for women to embark on a career in enterprise technology because of a lack of a supportive network in the field, Lin and her team created Work-Bench’s Women in Enterprise Series, a monthly forum for women in Work-Bench’s enterprise community and their #HacktheNetwork initiative which matches enterprise mentors and mentees.
Elana Lyn Gross: What inspired you to start Work-Bench? What was your career path?
Jessica Lin: My path to venture capital has really been the definition of non-linear and non-traditional and is something I can really appreciate and value.
In college, I studied international relations, African studies and Swahili and was ready and set to go down a career in global health. But I ended up taking an engineering class my senior year at Harvard that opened me up to the world of tech and innovation. After graduation, I helped to launch a design fellowship for Harvard students in Cape Town, South Africa and advised small teams of student startups.
From there, I took another left turn by joining a large tech company, Cisco Systems, where I worked with high-performing engineering teams undergoing a massive Agile transformation. I saw firsthand just how critical culture, processes and team were. The funny thing is that whether you are at a large or small company, these team, culture and process questions are universal. Your people and your teams are your greatest asset.
In 2014, I cofounded Work-Bench with Jonathan Lehr, as a venture fund and community to identify, support and invest in the next-generation of enterprise technology startups. Over the past three years, we have invested in 18 world-class enterprise startups, built a home and hub for enterprise tech here in NYC with our 32,000 square foot workspace and host more than 200 enterprise-focused events a year.
Lin: It is really hard to build and scale a startup. Building an enterprise startup is even harder. Facing incredibly complex technical products and legacy systems, notoriously long and difficult sales cycles, procurement, contracts and security audits, it is daunting even for a seasoned founder. At Work-Bench, we know these challenges require expertise – from other entrepreneurs who have done it before, and from a corporate network, who can give you insights from the other side.
So why do it alone, when you can go forth with others?
Over the past three years, we have built a dynamic enterprise community engine and a corporate engagement machine of Fortune 500 executives – what we like to call, the intersection of suits and hoodies. We have a community of over 18 portfolio companies and 28 member companies who work out of our 32,000 square foot community workspace to foster collaboration and shared learning. Furthermore, through our corporate engagement and executive briefings machine, we have been able to help close millions of dollars in Fortune 1000 enterprise contract value through our strategic customer introductions.
I am time and again moved by the willingness and generosity of people in our network, from serial entrepreneurs to corporate executives, who help support and share their time and expertise with other startups. I believe this network effect is really rooted in an understanding that we’re all of fighting the same good fight, to bring transformational technologies to the biggest companies in the world.
Gross: What has been the biggest challenge and, on the flip side, the biggest reward of starting Work-Bench?
Lin: What many people may not realize is that building a venture fund is very much like building a startup. You have to hire great people, build a brand and be selling and hustling in order to support your portfolio companies and identify great companies to invest in.
The biggest reward, hands down, is working with incredible teams to support them on their brilliant visions. It is something I never take for granted – getting to work alongside and support smart, passionate, hardworking people.
Gross: Work-Bench has made supporting women in enterprise tech a priority with #HacktheNetwork. How does it work?
Lin: We all know that we need to support more women getting into in enterprise tech, but there is no easy silver bullet. So what could we meaningfully do at Work-Bench to close the gender gap in enterprise technology?
One of the biggest challenges that I even experience personally is breaking “into the network” when it is predominantly men. We thought about what assets we have, and it was very clearly our 15,000-person network across enterprise startups, corporate executives and investors.
Given the breadth and depth of our community across both men and women in enterprise technology, we are using our #HacktheNetwork initiative to connect mentor pairs, to help support more women in enterprise technology and to ultimately help grow and diversify the enterprise tech network.
Gross: What advice do you have for other women who hope to start their own businesses?
Lin: At every stage, there will be something that will be hard and there will be different pressures. But the one that sticks with me is to not be afraid. As women, we’re told all the time to be fearless. But as you build more, you will naturally have more to lose and more to fear. It will feel harder when you have a team, a business and others relying on you. But you have to push through that fear of failure, at every stage, and keep trying and learning and taking calculated risks and being comfortable with experimenting – because that innovative and creative spirit is so important to continue to breakout.
Gross: What are your responsibilities as cofounder and general partner of Work-Bench?
Lin: As a general partner, we identify areas for investment, meet great companies and support companies in our portfolio. My area of focus is in the future of work and future of teams – the consistent thread we see across large companies and small startups. Your people are everything. So how do we use technology to enable our people? I’m particularly interested in enabling strong managers and also how we will consume and absorb knowledge in the future, as our jobs and roles at work continue to evolve.
Gross: What are three characteristics you look for when you’re hiring a new team member?
Lin: My number one interview question is, “If needed, will you change a light bulb?”
No matter how big we may get, we will always value one’s startup hustle to help our companies and community succeed.
Second is grit grit grit. Just as we see our companies hustle – whether for customers, top talent or fundraising we too expect our Work-Bench team to hustle for our portfolio companies in making strategic introductions to customers through our Executive Briefings, in advising them on press relations and on hiring the best team members.
Third is creativity. This feels undervalued in venture capital, but in a fast-changing space, can you be creative and come up with new solutions whether it is supporting a portfolio company, identifying new areas of domain expertise or differentiating our brand and work?
Gross: What are the most important skills for doing your job and how did you develop them?
Lin: Soft skills, asking questions and selling. One of the hardest parts of the job is having to self-teach. You have to first chart your own path as a venture capitalist, and then follow it.
There is no one book to read or class to take to be a successful venture capitalist. This is something I continue to work on: defining my own professional development plan through my hard and soft skills, mentors, what I read and meeting new people.
Gross: On the side, you’re working on Teacher’s Tech Tours. What’s the project’s mission and how do you achieve it?
Lin: Outside of work, I have been a longtime general educational development (GED) educator for adults for more than eight years. I also have been working with LaGuardia Community College’s Technology and Innovation Initiatives group, and serve on their New Media Advisory Board.
Sitting at the intersection of education and tech, I see so clearly how there is a deep need to connect tech back with education – specifically, how educators can learn about what is happening in the workforce and how they can apply these rapid jumps and leaps back into the classroom to best prepare students for the future of work. The premise for Teacher’s Tech Tours is to bring professors to meet with many of our tech startups here in NYC to understand the latest trends and tools
Gross: What is the best advice you’ve ever received?
Lin: Embrace what sets you apart. When times are hard, you’ll want to be like everyone else. But being like everyone else doesn’t get you ahead.
Gross: What is your business advice for other young professional women?
Lin: Work with good people. Companies will change, products will change and your role will change. But if you work with great people, you will always learn and grow.
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