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Zooming in on Way Finders’ Board member Leonard Underwood

November 20, 2023

If you’ve attended a celebratory event in or around Springfield over the past two decades, chances are you’ve crossed paths with Springfield entrepreneur and Way Finders’ Board member Leonard Underwood, of Underwood Photography.

“I always say I live vicariously through people’s events,” said Underwood, who is also the owner of Upscale Socks. “I photograph four or five parties a week. I’m preparing for a wedding today at Look Park, tomorrow I have a sweet sixteen. And Sunday, an event at the Springfield Museum. So I’m attending parties, dressing up, having conversations with people.”

One topic of conversation that he’s glad to see receiving more attention these days is the region’s crisis of housing affordability and availability—and Way Finders’ role in helping to solve it.

“The need for Way Finders’ services is certainly great, especially among young people. Way Finders is definitely filling that hole or that gap when it comes to housing, and being that epicenter, if you will, for housing resources,” said Underwood, who joined the Board of Directors in 2018. “I’m so glad that the organization is being amplified even more through media coverage, TV spots, and interviews. Way Finders is a gem in the community, a beacon of light and hope.” 

Underwood, who has worked on and off for the past 20 years as a substitute teacher, notes that most people he encounters in the community are familiar with Way Finders—especially at mention of the newly constructed Springfield Housing Center at 1780 Main Street. 

“People ask me questions about programs, such as RAFT [Residential Assistance for Families in Transition], and how they can get support for their family members or for themselves. And they are always very thankful for the work that Way Finders provides,” said Underwood. “I have a former student who has been homeless, I told him about RAFT because he was in dire need and didn’t have other people to reach out to—or he has been told ‘no’ enough times by them to not even bother asking.”

When Underwood was first approached in 2017 with an invitation to join the Board—by current Board Chairperson Jasmine Naylor, an acquaintance from high school that he connected with while working local events—he was drawn by the chance to be a part of something bigger than himself. And to represent his community, with care and compassion.

“Representation is important. I was born and raised in Springfield and remained here for college and to buy a home and all of that. As a first-generation business owner and board member, I don’t have anyone to show me the ropes, like an uncle or a father or grandfather,” said Underwood. “Being in this type of formal Board setting, with high level professionals, can be kind of intimidating, and not everyone looks like you in the room. I’ve been learning as I’ve been going along. I’ve learned a lot over the last five years and built confidence to share my voice.” 

One thing Underwood has learned more about is the need for fundraising, which allows Way Finders to be more responsive to client needs and offer greater support, and how donations of all sizes make a real difference. By serving on the Resource Development committee, a natural fit for his business acumen and extensive network of community connections, he has helped Way Finders identify donors, partners, and future candidates for board service. In 2021, he also joined the Board of Way Finders’ subsidiary Common Capital, Inc.

“As a business owner, I’m always thinking about the future,” said Underwood, who intended a future in litigation until a summer internship helped him correct course. “So for Way Finders, that means thinking about how we can solve this housing crisis in the Commonwealth and what that will look like in the next five to ten years. Seeing the progress of late has certainly given me hope, knowing that we’re moving in the right direction. Way Finders has great leadership, and I’m glad Governor Healey is on board with prioritizing housing.”

When asked to reflect upon highlights of his time spent serving the Board, Underwood—ever the photographer—zooms in on events. 

“Seeing the new Springfield Housing Center on a tour with [Way Finders’ President and CEO] Keith Fairey and a few other members, we were in the pandemic so we had to do it very staggered. But it was really poignant, seeing it completed and how our contributions went to a good cause,” said Underwood, an avid exercise enthusiast and runner. “And at the 2021 ribbon cutting for Library Commons in Holyoke, it was really nice to do the walkthrough, hear from tenants, and see the value these beautiful spaces bring to the neighborhood.”

It’s important to Underwood that staff know the Board cares—that they have them in mind when they’re making decisions. 

“That’s why I do my best to show up and be active and engaged as much as possible,” said Underwood, who envisions sunsetting his photography business in the next few years in favor of teaching business. “Because you get to see things in real action, put a face to a name, interact with employees. Meeting people at the September staff picnic at High Meadows Retreat, that was really good, too.”

Thank you for your Board service, Leonard Underwood!