Joining Work-Bench VC

Reflecting on my first month as a VC

Big News

I recently took a leap of faith and moved back to NYC from Chicago to pursue a dream job — I joined Work-Bench on the investment team! 

Work-Bench is a seed-stage venture capital firm investing out of its third fund, a $125M vehicle. We lead $3M - $6M Seed rounds in software startups, primarily focused on Artificial Intelligence & Machine Learning, Cloud Infrastructure & Developer Tools, Cybersecurity, and the Future of Work. Some of our breakout portfolio companies include Cockroach Labs, Socure, Spring Health, Dialpad, and more. Our differentiation stems not only from our enterprise chops, but our success in building NYC’s largest enterprise tech community and our laser focus on supporting early-stage startups on all things go-to-market.

~In a future post, I will detail my journey to VC and how Startupon helped me differentiate myself and land offers~

During my initial conversations with the Work-Bench team, it became clear that real-world operator experience can provide a unique value add to early-stage VC firms and their portfolio companies. My lived experiences across Machine Learning product management and enterprise GTM strategy at Hyperscience and IBM serve as foundational building blocks for helping founders ship product and operationalize their sales efforts. But first, I wanted to take a step back and reflect. 

During my first month(ish) as a VC I have been exposed to all facets of the investment process from deal sourcing to due diligence to board meetings and more. Now, after four(ish) weeks on the job as a VC, I wanted to share four learnings — the things that surprised me the most, proved more challenging than expected, but also what make this job particularly fun and exciting: 

Context Switching is Everything

While we’re dedicated to enterprise software broadly, each team member focuses on their own sub-vertical(s) to maintain the requisite expertise to evaluate new opportunities in a sector and support their relevant portfolio companies. In these early-days, I am sticking close to what I know in Machine Learning, Application Software, and Developer Tools. During our weekly investment committee meetings, the conversation can regularly switch from new deals we’re looking into (which can span all segments of software) to helping portfolio companies raise their Series A to introducing a potential Head of Sales hire. Additionally, we are constantly planning internal and external community initiatives, like our New York Enterprise Tech Meetup, Womenterprise community, and much more, which help us tap into the broader enterprise tech ecosystem and give us leverage to source, win, and scale future investment opportunities.Being able to parallel process these various responsibilities we take on investors helping build out portfolio, the broader ecosystem, and also our own Work-Bench brand is key. 

VC is Fiercely Competitive

To an outsider, one might assume that VCs simply choose which founders and companies they want to invest in and the deal is done. However, that’s only half the equation. The investment process is like a marriage where two parties need to come together and mutually decide that they want to team up for the next 10 years. There are certain instances where a founder really likes a certain VC, but the VC doesn’t find the company or founder compelling. On the other hand, there are times where VCs try hard to win a deal only to lose to another fund. This can happen for a variety of reasons including giving more favorable terms to the company, promising to help the founder in ways other VCs can’t offer, or by simply providing a stronger brand to founders to help with future hiring. Each of these has tradeoffs, but the underlying VC investment process is fiercely competitive.  

A Prepared Mind Goes a Long Way

There are a lot of VCs out there and while fundraising is not easy, founders have a lot of options. Specializing in enterprise software has given Work-Bench an edge with technical founders. By demonstrating a deep understanding of emerging categories, the firm can get conviction in companies before other funds. Work-Bench co-founder Jon Lehr has written about this before elaborating on how the concept of proprietary insights comes into play. He said that “whereas most enterprise VCs will assess a variety of common SaaS metrics in order to get enough conviction to invest in a company, at Work-Bench we can get conviction ahead of others by using feedback from our Fortune 500 buyer network as part of diligence.” In my first month, sticking close to what I know in machine learning and usage-based pricing has already earned me some brownie points with founders. Being able to speak the same language is imperative to understanding the vision for what the company can become and any hurdles it might need to overcome. 

Therapy Included

Having sat in on my first few board meetings, sometimes VCs just need to be a shoulder to lean on. Founding a company is an incredibly challenging and emotional effort that many outside the industry don’t understand. While there’s a time and place for helping founders with go-to-market or hiring a head of sales, sometimes you just need to be empathetic and listen when the inevitable doubts may arise after a rough quarter, a senior hire that's not working out, or a grueling fundraise. Besides offering advice and potential introductions to help, oftentimes a founder may just need you to reinforce your conviction in the company and their strategy to help them power through the rough patch and keep scaling.

Reach Out

As always, if you’re looking to launch your own company, interested in joining a startup, or curious about breaking into VC, simply respond to this message. 

You can reach me at daniel@work-bench.com.