Jessica is a Co-Founder and General Partner at Work-Bench, focusing on enterprise software investments in future of work. Prior to Work-Bench, she worked in Learning & Development at Cisco. Jessica is actively involved with workforce development in New York City as a longtime GED educator and as an advisor to LaGuardia Community College.
What attracted you to venture capital and enterprise technology in particular?
I’m really lucky that Jonathan Lehr and I - two enterprise nerds - were brought together by some of the founding advisors of Work-Bench. My co-founder Jon came from Morgan Stanley’s corporate IT team. In his spare time, he founded the New York Enterprise Tech Meetup, connecting an ecosystem of 5,000+ entrepreneurs, Fortune 500 technologists, and investors. I was at Cisco Systems in Boston working with engineering teams on agile software transformation. Prior to that, I co-created a design and innovation fellowship for Harvard’s student startups in Cape Town, South Africa.
I’m drawn to people who are passionate - a characteristic I saw in Harvard’s student founders and engineers at Cisco. In the enterprise space, there are people who care deeply about this area and the painpoints within it. It was the right place and right time when we started Work-Bench and cultivating this burgeoning enterprise tech community here in NYC. These past five years have been an incredible ride. We’ve made over 25 investments throughout the United States and built a hub for all things enterprise with 200 events a year and 20 startups working in our space.
People say that they’re bullish on New York tech even though it’s a smaller ecosystem than San Francisco. What makes NY a great place to build this enterprise community?
In New York, five years ago, there were probably 2 or 3 major enterprise software companies. Work-Bench has grown with NYC’s tech ecosystem, and we’ve also tried to contribute to this growth too. New York has seen over $5 billion in aggregate venture funding in enterprise startups since 2013, with lots of attention and funding coming from West Coast VCs too.While New York has had its roots in adtech and e-commerce, we’re very firmly now in this rise of enterprise software and deep technology being built here. There is a lot of cross-pollination between individuals in large corporates moving to enterprise tech startups and vice versa, and we have a strong university ecosystem too with NYU, Columbia, Cornell Tech, and others. New York also has the breadth of enterprise: diverse companies, numerous industries, customers, and deep expertise.
What did your sourcing process look like when Work-Bench was new and relatively unknown?
Given our community-focused approach and all of the events we organize, hopefully if people are building an enterprise startup, they’ve heard of Work-Bench.
In the beginning though, we had to experiment with the best ways to create our community. Launching events, putting content out there, ideating… the whole design thinking mindset. It’s given us a pretty good understanding of what actually works, and we tailor our events and our advice to provide high impact for our startups.
There also weren’t as many enterprise tech startups back in 2013. So our team has had to be nimble about finding the best startups - which meant investing in the West Coast and across the U.S. An important part of our investment strategy is that we don’t just invest in cool technology and pitch that back to corporates. We engage with our network of corporate executives in New York City to reach end customers at scale and identify their pain points, so that when we find relevant companies the introduction ends up being mutually beneficial. This information helps us ideate and hone our investment theses. We also draw on what we see, trends we read and hear about - then we go out to find the right startups to invest in.
How closely do you work day-to-day with portfolio companies?
We have a number of companies that work in our space including startups that aren’t in our portfolio. We do that intentionally. We invite in companies that we admire and respect; it’s another way we build a great enterprise tech community.
We’re very hands on investors in a way that (we hope!) is helpful to founders. One reason is our laser focus on enterprise sales. We invest in post-seed or pre-series A companies where customer acquisition and sales are the biggest challenges. For many of our companies, we meet every 2 weeks for sales pipeline reviews. We help analyze accounts; finding ways to help with backchannel; rethinking proof-of-concept negotiations and procurement. This is where we really deploy our corporate executive network and personal backgrounds in corporate IT, and it is value add in a way that almost no other VC can compete.
Over these past five years, what have you observed about women in technology and VC?
Though NY has a strong number of female founders, women in tech is still an uphill battle. The problem is even more acute for women in enterprise tech. Our startups and corporate partners recognize this challenge, and we’ve made a concerted effort to ensure that we’re bring women to enterprise tech and making it an area where they can thrive.
In February, we hosted the first-ever Navigate 2018, our women in enterprise tech summit in partnership with Salesforce Ventures. It was an unbelievable success with 250 women; we were featured on the Nasdaq Tower in Times Square and had an amazing article in the Wall Street Journal. Through our sessions and talking to attendees, Navigate showed me that I wasn’t the only one trying to empower women in enterprise tech. It’s an important mission that Work-Bench will always be committed to.
Have you found your mentors in the enterprise tech or VC community?
Definitely. In this post, I have written a list of tips on how to better network because calendars for venture capitalists get wonky so quickly. We’re always thinking about ways to effectively allocate our time. In fact, I’ve started hosting breakfasts once a month in Union Square to bring together awesome women in tech. My mentors aren’t just people in enterprise. I think it’s important to learn from female leaders throughout tech, and hosting these breakfasts is a way I bring them together to build connections with each other as well.
Have you faced major challenges in the VC space and how did you overcome it?
For better or for worse, I’ve always been one of the few women in the room. People have also told me that I look young for my age (which I will accept as a compliment for now :). I’ve been so lucky that my co-founder Jon and my entire team are such big supporters and everything we do here. My general philosophy is to surround myself with good people who will champion me.
The general view in VC is that the more time you put in, the better positioned you are to help founders because you have a more robust network, more data points for pattern matching, etc. But I also think you can always bring a fresh perspective and dynamic, different way of approaching a problem.
Women who are VC veterans have told me that you do hit a sweet spot from an age perspective – when you’re not too young, you have enough experience, and you’re seen as an asset. But until you get there, you play to your strengths. That’s the approach we’ve taken at Work-Bench: we don’t want to be the smartest people in the room because we’re focused on bringing sharp minds across our advisors, experts, and company builders to the table.
What advice do you have for young women who want to enter VC or enterprise technology?
My advice would be to do exactly this! Have a side hustle, reach out to people and create value in trying to connect people. This is advice I’d give anyone - not just women interested in a career in venture. So much of VC is meeting people, gathering data, and demonstrating your points of view. Start blogging! Find an area of interest and write about it - and don’t worry if you’re not an expert because you don’t need to be. The act of learning and being curious, that’s something people look for and appreciate.