Building the Miami Heat of Enterprise VCs

Jonathan Lehr
Feb 6, 2020 · 6 min read

We’ve launched the “Making of a Manager” series to share our top learnings as General Partners building and scaling Work-Bench for the past 6+ years. Read on for more in our series.

For NBA fans this season there’s been a bit of a surprise atop the NBA rankings. Despite their star player Dwyane Wade retiring last year and no other superstars like LeBron James, Kahwi Leonard, or Giannis Antetokounmpo on their roster, the Miami Heat are the 3rd ranked team in the entire NBA. When NBA Analysts made their projections before the season started, nobody expected the Heat to play this well.

Aside from being born and raised in Miami as a huge Heat fan, the Heat’s surprising season has also been on my mind as I reflect ahead of a massive Annual Meeting that I’m attending these next few days for our LP Greenspring Associates.

Greenspring is one of the best in the business and has invested in many of the top VC franchises such as Accel, Benchmark, Bessemer, Lightspeed, NEA, and Scale Venture Partners.

So how do we at Work-Bench hang with the big dogs?

The answer lies in unpacking the parallels in what makes the Miami Heat and Work-Bench so special.

1. Identify overlooked talent

Miami Heat: The Heat have historically had a keen eye for finding talent outside of lottery picks, especially when it comes to players undrafted (and overlooked) by other teams. Heat center Bam Adebayo was the 14th pick in the 2017 draft and is in the running for Defensive Player of the Year. Tyler Herro was a late draft pick who is now fearlessly scoring big bucket after big bucket in the clutch. And Kendrick Nunn is the first undrafted player in NBA history to win Rookie of the Month honors twice in a season. Combing this talent with the Derrick Jones Jr’s highlight reel dunks (see an example below) and you’ve got a winning team that’s incredibly fun to watch.

Work-Bench: When you think about the team we’ve built at Work-Bench, our backgrounds are mainly from the corporate IT world. Historically these personas have been “undrafted” in venture, and speaking from my own experience in trying to break into VC in 2013 from Morgan Stanley’s Office of the CIO team in IT, most people overlooked us. As I’ll share later in this post, our team’s IT to VC experience from Morgan Stanley, Cisco, Bank of America, and Forrester Research is exactly what was needed in order for us to shake up the VC landscape.

2. True chemistry is a superpower

Miami Heat: It’s a thing of beauty to see genuine chemistry permeate an organization. For the Heat, friendship is coursing through their veins right now. Want to see what that looks like? Just watch this video below and check out this quote below from SLAM’s photoshoot.

Work-Bench: Culture is our secret weapon at Work-Bench. I found it ironic that many VCs talk about creating great culture at startups, but barely talk about building culture at their own firms. Meanwhile, given the continued rise of new funds being raised, fostering a collaborative VC fund culture is more important than ever. This is something that we put a lot of thought into at Work-Bench.

Community and corporate engagement are both key to our model. Unlike other firms, which split the investor and platform side of the house, all of us wear multiple hats. As I’ve shared previously:

By having that continuity up and down the “venture value stack” our value add runs deeper, is more consistent, and tends to be much higher leverage from an effort perspective. With no sense of “dumping a company” onto a services side of the house, the interactions remain fresh and companies can stay top of mind. This has an added benefit of helping promote better collaboration among the team to assist the broader portfolio, regardless of who is point on a company. By everyone exercising these community and corporate engagement muscles more frequently, when one of us has a specific ask for a company, we’re all able to do deep dives for meaningful talent or customer wins.

The other key element here are the tight bonds of friendship that have been forged on our team. We’re in the trenches together everyday trying to rethink enterprise VC, and this keeps us far more connected than the average VC on a weekly basis.

We also spend a fair amount of time together outside of the office — whether seeing concerts (Bowery Ballroom and Brooklyn Steel are our most frequented venues), spinning (we’re addicted to Flywheel), hosting team dinners and BBQs, watching Fast & Furious movies on premiere nights, binge-watching It’s Always Sunny episodes, competing at bowling, and lots more.

3. You need a secret sauce

Miami Heat: Heat President Pat Riley is known as running the best conditioned organization in the NBA.

This article explains the grueling and unique training every player completes, whether veteran, starter or rookie.

“We’re going to get you in world-class shape,” Riley told Waiters, as he recounted for The Players Tribune. “Not good shape. Not great shape. World-class shape. Give us a season, and you’ll see.”

Riley has made this promise to other free agents over the years, and he has an iPad full of before-and-after pictures that serve as success stories to back up his claim. When a player joins the Heat, it doesn’t take them long to realize that this organization does things differently.

This is what it takes to win championships, and these are the values that Pat Riley makes sure that his organization espouses.

Work-Bench: Our secret sauce is really not so secret: we combine our team’s unique backgrounds in corporate IT with our location in NYC — and the density of Fortune 500 companies here — to understand corporate pain points at scale. We then work backwards from pain point to founders to find the most exceptional enterprise startups tackling these problems. Then we play matchmaker.

Our work over the past 6.5 years has shown us that it is exactly this unique matchmaking that solves the most critical pain point for our founders: closing enterprise customers. We’ve been relentlessly focused on this mission and since most other VCs aren’t actively facilitating customer introductions in the process of getting to know companies, and certainly don’t nerd out on SOCII audits and Procurement challenges, or back-channel their networks at Fortune 500 companies to get the real deal on a POC or help unstick a negotiation, we’ve been able to make our mark and build a portfolio of extraordinary enterprise startups.

As the venture landscape continues to evolve and we witness interesting trends like the rise of Seed II rounds and NYC 3.0 as a booming enterprise tech ecosystem, we couldn’t be more excited about the opportunities ahead!

Before I go…

PS — Just because it feels so good, and I assume many of my readers will be Bay Area folks, here’s one more clip for y’all :)

Thanks to Kira Colburn for her helpful edits on this post!


Work-Bench is an enterprise technology VC fund in NYC.


Work-Bench is an enterprise technology VC fund in NYC. We support early go-to-market enterprise startups with community, workspace, and corporate engagement. Sign up to get our digest of top content & industry news weekly:

Jonathan Lehr

Written by

All enterprise tech, all the time || VC @Work_Bench, Founder of @NYETM, and @KauffmanFellows Class 19 || I also tweet (a lot) about the @MiamiHEAT


Work-Bench is an enterprise technology VC fund in NYC. We support early go-to-market enterprise startups with community, workspace, and corporate engagement. Sign up to get our digest of top content & industry news weekly: