2020: What We Learned (Updates to our Work-Bench User Manual)
Tags: Enterprise, Teamwork, Wbvc, Venture Capital, Lessons Learned

What’s Your Biggest Motivation?

JESSICA LIN: “For me, I still get the best high when our Work-Bench community just works. Even after 7 years in the making and now being virtual, I continue to be so touched when our community of portfolio companies and others help one another, and I get to witness our founders and operators connect, ask each other questions, provide their own lessons learned, and truly become a support group for one another as they traverse the ups and downs of scaling an enterprise software company. As just one example, we recently hosted a Head of Sales Roundtable, where a CFO and CRO of one of our late stage portfolio companies completely opened up about hard learned lessons they’ve acquired around pricing their platform. Given this is an area so many of our earlier stage companies are working through right now, it was so valuable for them to get this tactical real talk from a trusted member of the broader Work-Bench family. I’m truly grateful for our #nextgenterprise community who are so willing to be honest and vulnerable — only then can you truly help lift one another up.”

JONATHAN LEHR: “I love each and every day of Work-Bench because we get the best parts of VC and also the thrill of building a startup. Jess and I as co-founders set out to fundamentally rethink enterprise VC, and during the course of our days between working with incredible portfolio companies, sourcing new investments, engaging with our corporate IT community, and so much more, we experience the highest highs and at times the lowest lows. Our jobs are definitely not for the faint of heart, but I love a good underdog story and find the job very thrilling. Between continuing to scale Work-Bench and our impact, as well as growing the NYC enterprise tech community brick by brick for 9 years running, I wouldn’t trade my job for any other in the world.”

PRIYANKA SOMRAH: “At Work-Bench, we are all about flipping the script and experimenting with new and creative ways to step up our sourcing, research, and community strategies. What excites me the most is that while we do take the time to celebrate the small wins, we don’t let ourselves get too comfortable. We continue to ask ourselves, ‘how do we keep improving on our craft?’ It’s why we’re constantly working towards the next thing: there’s always a new deal in the making, there’s always a new content piece in the works, there’s always a new founder to meet. There’s no dull moment with the Work-Bench crew and it’s why we continue to grow and thrive as a team.”

What Challenge(s) Are You Tackling?

JESSICA LIN: “The most challenging question that I have had to tackle is ‘how do I keep my learning reps up?’ It sometimes feels like there are not enough hours in the day :) whether it’s a new technical area of investment, forward-looking research, or strategies, tactics, and challenges facing our portfolio companies…there’s always something new to learn. I’ve really had to learn how to make time to not only read and research, but continue meeting new people and connecting and sharing. Back in 2018, I wrote a blog post on a similar topic around how to best accelerate board expertise: “Growth Hacking Board Experience as a VC” and it still stands.”

KELLEY MAK: “The area where I’ve been trying to grow the most is being open minded. After spending time in one technical area for a while, it’s common to get preconceived notions that will make you immediately say yes or no. But part of the magic of this job is when you think you know a sector or something has played out, and then an incredible entrepreneur paints you a vision of the world that makes you rethink everything.”

KIRA COLBURN: “The quality I admire most in people is their creativity, but I also find it to be the biggest challenge to achieve. I’d argue creativity isn’t in everyone’s DNA, yet it’s important for everyone to have. In essence, it’s all about challenging yourself and your work to be like nothing else out there, all while staying true to your personal and professional brand. While there’s a clear link between creativity and content (which is what I lead here at Work-Bench), it’s also important for all aspects of business as it helps solve problems, boost productivity and confidence, and just generally make the work day more fun.”

What’s Your #1 Lesson Learned from 2020?

JONATHAN LEHR: “You’ve gotta enjoy the ride, and the best way to do that is by working with amazing people. I’ve written before how true team chemistry is a superpower, and it’s especially true for a small team who punches way above our weight class in the deals we do and value add we provide to our portfolio companies. I find it ironic that many VCs talk about creating great culture at startups, but barely talk about building culture at their own firms, and it’s something that we’re very intentional about at Work-Bench.”

KELLEY MAK: “My biggest lesson learned so far is how to take the ups with the downs. We often joke that VC is a sinusoidal wave, or the craziest ride in a theme park — a mix between a roller coaster, maze, and haunted house. While we obviously want to win, the fact is there are losses along the way. I’ve learned how to improve from them, celebrate the victories, and continue to enjoy the process.”

PRIYANKA SOMRAH: “One of the biggest learnings for me has been the importance of cultivating a strong network of trusted relationships with fellow VCs who support and elevate each other. While building authentic relationships is a lot of work and takes time to mature, I’ve come to realize that having a close-knit group of people that I can trust and turn to for advice and feedback has been so critical to my growth both as a person and as an investor.”

KIRA COLBURN: “Writing is whatever you want to make it. While there’s a ton of buzz of what’s worked for others and what’s most popular now, there are truly no boundaries or rules to what you can and can’t do with your own content. In fact, it’s better to break out of the norm and differ your brand and voice as much as possible. Whether through tone, language, format, visuals, etc. the sky’s the limit, so get creative.”