VC Profile: Underscore’s Jenni Goodman

Jenni Goodman is a Community Manager at Underscore, a Venture Capital Firm that uses an innovative community model for their portfolio companies.

Underscore Community Manager Jenni Goodman (Courtesy of Underscore)

Niche. Domain expertise. Master of One.

Innovation’s cultural zeitgeist has progressed towards idolizing those who specialize in hyper-specific subfields. I applied to college recently, and that sentiment was apparent in the countless online forums where embattled teens argue over application “spikes” and “hooks”.

To adherents of this new orthodoxy, Jenni Goodman has followed an unorthodox route. Skilled in logistics, planning, and relationship-building, she didn’t followed one pre-determined path. After graduating from Boston University in 2008, she worked in various jobs for various companies, from Pfizer to career management firm GetFive. She wasn’t quite sure what she wanted to do, but working in different industries helped her generalize her toolset across a broad range of functions.

Eventually, Jenni found her calling in startups. Her people-skills and planning abilities would transfer well to entrepreneurship; after all, employees at early stage companies often perform disparate duties. And in 2016, she had the opportunity to attend Babson for an MBA and collaborate with entrepreneurs. Her new job was at MassChallenge, a non-profit startup accelerator based out of Boston.

MassChallenge introduced Jenni to the diverse and fast-paced world of startups. There, she led their Health Tech Community. As a community manager, she experienced the trials and tribulations of running an early stage company, connecting founders with opportunities, customers, advisors, and resources to supercharge their growth. While it was tough, the experience helped her pick up dozens of skillsets from product marketing and technology to sales.

Jenni enjoyed her work at MassChallenge. She was absorbing a variety of skills and talking comfortably to people in different fields. And that’s when she got a call from Underscore. 

Michael Skok was a former investor at North Bridge Capital before he founded Underscore in 2015. Frustrated with how VCs was being run, he decided to talk directly with founders to learn what they needed. After speaking with entrepreneurs across the country, he discovered that many startups were talent-strapped. They needed incredible first hires to shoot their companies to stardom, and they needed mentors to guide that rocket-ship of growth. So when Skok returned to Boston, he founded Underscore.  The firm would provide the requisite capital, but it would also introduce a Core Community, a hand-built network of Boston business operators, leaders, and founders. 

Underscore is Boston-Biased; they focus on Boston companies and the Boston startup ecosystem. Jenni also saw Boston’s potential from her time at MassChallenge, and acknowledged its lack of national coverage. Her dreams of putting Boston’s startup scene on the map meshed with Underscore’s investing ethos, so taking a job at the firm seemed like the right move.

Jenni would manage Underscore’s Core Community. And while most investors are hired because of niche domain expertise, Jenni pointed out that her multifaceted experiences landed her that job as a community manager.

She elaborated, “I didn’t have the typical venture career path, but because I had my hands in so many different things, that actually turned out being very helpful. I was more of that master of none, but that meant I got to touch a lot of different functions that are really important to my role now. I didn’t pigeon-hole myself which gave me the experience to know a lot about everything.” In other words, being a generalist had beaten being a specialist. Connecting Boston’s startup community would take a wide breadth of knowledge, and she had built just the skillset to do so.

To build a community is to juggle multiple different tasks. Jenni needed to understand the startup ecosystem’s needs to provide resources for Underscore’s companies. She also had to connect leaders in the community, encourage people to invest time and money, and drum up excitement around the Boston startup scene. “The goal is for people to eventually move to Boston and want to start their companies here.”

Luckily, those goals are intertwined. Building an incredible ecosystem helps new companies gain traction faster. More traction encourages community members to get involved. Increased involvement drives more public attention.

To grow the community and keep members engaged, Jenni and Underscore have implemented several strategies. The most visual component is their online portal. At first glance, Underscore’s Core Community website looks like a pared-down LinkedIn. You can search through their directory, make connections, and find a diverse set of professionals ranging from CEOs to sales managers and product heads. But the group is more niche, focused on Boston and startups specifically. There’s also a list of weekly events you can sign up for, giving members the chance to network and listen to industry experts.

But the main benefit of the Core Community comes to founders in Underscore’s portfolio. Those companies can immediately access a highly-vetted network of mentors and people to help their sourcing needs. You could call it a Boston alumni community of startup founders and leaders.

Getting into Underscore’s portfolio means embodying the ethos of their investing strategy: community. Underscore looks for the same traits in founders that would be useful in a Core Community member: grit and the ability to take feedback. “Taking feedback from your community and customers is an incredibly important trait to be able to succeed. And we’ve had issues when we’ve realized this person is not someone who could potentially succeed because of stubbornness and an inability to take advice from others,” Jenni added.

Investors balance risk and move capital into startups’ hands. Jenni takes the next step by providing nourishment and turning those investments into successes. 

Among the resources provided for portfolio companies is the core partner program, which helps founders find powerful advisors without giving up control. Many founders have trouble finding mentors to guide them, and when they find qualified individuals, they often have to sacrifice considerable equity to attract them. To solve this, Underscore gives away their own stock to potential advisors. Founders can therefore leverage high-powered individuals with limited downside. 

Startups can also access the Founders’ Core Forum. Running a startup can be isolating, so Underscore wants to ensure that all their founders are connected.

Monthly, the founders that are a part of Underscore will meet. They’ll discuss various topics. When this started, our topic was about the new normal and how people were handling everything. We discuss a variety of topics, and having a forum where our founders can connect and talk with each other has been incredibly important.

Especially during the coronavirus, when everything has changed, having a backbone of support can be super great. “How do we deal with employee engagement? What are we going to do with our leases where we’ve a signed a five year lease and no one is using it? And that’s a lot of money. How are we thinking about hiring or layoffs or saving cash?”

Ultimately, whatever’s on the founders’ minds is on the table for discussion. Whether it’s wellness, mental health, or current events, it’s a great way for them to trade tips, blow off steam, and become better acquainted.

While Covid-19 has introduced wrenches into many founders’ plans, it hasn’t stopped Underscore’s Core Community events. In fact, planning’s easier. Instead of booking a restaurant and inviting people to attend during a block of time, Underscore can host everything online. Virtual meetups also offer a different sense of closeness in comparison to real-world events. “If you want to have a small, intimate discussion, you could really just have a couple breakout rooms on Zoom. And I think people are just excited to engage because they miss being around people so much that the need for a community/conversation is larger nowadays.”

The Core Community has taken off. Since the last time I checked, there are hundreds of active members in the Core Community portal, and many are there to give back. Jenni said, “so many people get where they are in their career because they had an advisor or mentor and, now, want to do the same for someone else.”

A Core Community Event

In her two years at Underscore, the startup landscape has shifted, especially given the constraints of a pandemic. However, there is one constant: building a community is hard. People have conflicting schedules. Engagement is sometimes slow. And the topics that people care about are always changing.

But Jenni has a great support system. Her current boss, Jimmy, the CFO at Underscore, lets her have full agency over decisions. “He’s the type of person to be here for advice if you need feedback, but he won’t instruct you on what you have to do. He wants to be that person that helps you walk and talk through things.”

Just recently, Jenni returned to Underscore after being on maternity leave, and felt overwhelmed with everything that was going on, between the coronavirus and scheduling new events. Having someone who could guide her where she needed and see the big picture despite the difficulties helped her keep a level head. Just like it takes a community to build a startup, it also takes a community to build a community.

VC Pitching Tip

Ask for feedback. Even when you’re giving your pitch, just ask. Did that make sense? Do you have any questions? How can I improve on what I’m talking about? After workshops, send a thank you email and correspond. I love when people ask, what could I have done to improve that? So someone who is always eager to learn and improve themselves is someone you want to invest in because they realize that things can always be better. They want what’s best for their companies and they want to have the best product.

Entrepreneur Advice

Learn as much as you can about the venture space, startup ecosystem, and founders. Reach out to people to get coffees and interview them to see what they’ve learned and what they’ve done. And the more connections you have in that space, the easier it will be to succeed. Reaching out to people cold is very different from warm intros. Get involved more in the ecosystem.