Jessica Lin

Origin Story: In a couple sentences, how would you describe your path to becoming an investor?

You may know the Work-Bench team as “IT to VC,” with backgrounds in corporate IT. However, before my career in IT, I studied International Development and Swahili in undergrad with the intention of a career in global health. Serendipitously, I took an engineering class my senior year of college that led me to work with student startups. Then serendipitously again, I took on a role at Cisco Systems as a Learning and Development Manager, working with best-in-class engineering teams.

My story is the ultimate story of pivots, which has led me to live and breathe our motto at Work-Bench, which is that “great things happen at the intersection of suits and hoodies.”
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Investment Approach: What are the key factors you consider when evaluating a founding team?

Work-Bench has a thesis driven approach where we first work with Fortune 500 executives to identify their top paint points, and then go out to find the best enterprise software startups solving those pain points and simply play matchmaker between the “suits and the hoodies.” We love when founders’ backgrounds and experience directly align with the problem they’re solving. For example, Catalyst’s Co-Founder and CEO led Customer Success at DigitalOcean before building a startup with a modern customer success platform, and FireHydrant’s Co-Founder and CEO was an SRE at Namely and DigitalOcean before launching his incident response software for SREs. Having felt a pain point firsthand is an invaluable experience when building a startup in that space.
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What's your style and approach when it comes to working with founders post-investment? What are the characteristics of founders you've worked well with?

The Work-Bench team knows how challenging enterprise go-to-market is, and we are humbled to hustle alongside our founders during the process. We love rolling up our sleeves and getting into the trenches with our founders directly. We’re on Slack, text message, and Whatsapp constantly - days, nights, and weekends (seriously). We focus on all the things that make building a world-class enterprise software company hard and we lean in hard - everything from navigating procurement, negotiating POCs, understanding SOC 2 audits and more (see our Enterprise Playbook Series at www.work-bench.com/playbooks). More specifically, we are obsessed with helping founders figure out their repeatable enterprise go-to-market motion. We do so through direct customer introductions, back-channel support, and tactical guidance on building out their go-to-market functions and sales efforts.

While almost all of our founders are technical (given the technical nature of enterprise software), we admire founders who also have “sales grit.” Enterprise software isn’t the sexiest topic to sell, so having a founder who can double as a sales champion with a passion, fire, and drive for enterprise software makes a world of difference.
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If I'm coming to pitch to you or your firm, what's the one piece of advice you'd give me?

The #1 piece of advice I give to founders is to paint the story of a larger and long-term vision for your company. Too often, we see pitches for features, rather than massive markets that founders are taking on and tackling.
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How would you describe your own personal mission and values, and how do they impact the way you invest?

As the daughter of immigrants, my life has been driven by the appreciation that service to others gives life purpose and meaning. Outside of Work-Bench, I am a longtime GED educator, where I tutor adult students on high-school equivalency and college prep. This drives why building a dynamic and giving community at Work-Bench has been such a meaningful and important experience in my life. Over the past 7 years, it’s been amazing to see how our enterprise community of founders, operators, corporates, and others support one another to help tackle the biggest enterprise challenges together and knowledge-share. This support system has proven even more crucial as our world’s were turned upside-down and moved online, at home during the pandemic.
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What do you like best about investing in NYC, and what’s your outlook on the future of NYC tech?

The pizza :)

Building a hub for all things enterprise tech in NYC has been a part of our core mission since starting Work-Bench 6 years ago and we continue to be extremely bullish on investments in enterprise software in NYC with over 70% of our portfolio based in the city. We believe the next generation of enterprise tech giants will come out of NYC, given its density of Fortune 500 customers and the incredible advantage of building next to your customers. Since 2014, there has been over $13B of venture funding towards enterprise startups in NYC alone. Our recent “State of Enterprise Tech in NYC: 1H 2020 Funding Report” (check it out at www.work-bench.com/blog) proved that NYC enterprise software continues to grow, with Q2 2020 setting record highs for deal activity and deal value since 2014, despite challenges from COVID-19.