Comedian and Founder, The Kind Squad
She Leads Thousands of People Whose Small Gifts Make a Big Difference
Jess Miller has survived plenty of struggle.
She lost her mother to a divorce when she was 8, then had a traumatic experience in the Army, then lost her mother again — this time permanently, to suicide — a few years after that.
But difficult experiences can be motivators, too — in her case, to spread kindness in a hard world.
“Being kind is just caring about people, right?” she said. “If you’re kind, you actually care about doing good things for other people. That’s kind of my philosophy.”
It’s a credo that led to Miller performing stand-up comedy starting about 15 years ago and turning those shows into benefits for local nonprofits — and, eventually, to her creation of the Kind Squad. First a Facebook page launched in 2015 and now an official 501(c)(3) nonprofit, it’s essentially a collection of people who gather online to donate to fundraising drives aimed at helping people in need — or just making someone’s day.
Miller explained the humble origins of the organization. In 2020, during the pandemic, she wanted to do something to contribute to the community and started a campaign called Art Kits for Foster Kids, posting about it in the Facebook group to solicit donations.
One member expressed interest in donating, but mentioned not having enough money to pay her own water bill. Miller calculated that, if 100 people donated $3 each, they could help cover the bill. So they did, and the model was born — what is now thousands of people who take up the call for small donations that collectively add up, leading annual campaigns ranging from Art Kits for Foster Kids and Mother’s Day Flowers for Foster Moms to the pre-holiday Western Mass. Toy Drive, which, this past December, collected more than $100,000 in toys, which were distributed in partnership with numerous agencies.
“The Kind Squad is built on a simple but powerful mission: to show children and families in need that they matter — and that their community truly cares.”
In all, the Kind Squad has raised approximately $300,000 not just for those annual campaigns, but for one-time requests that come in from across the region — and the entire U.S., for that matter.
“Maybe this homeless shelter needs a little jungle gym. I literally write everybody’s donations out, I buy the stuff, I put the receipt out — 100% in, 100% out. And that’s kind of how we’ve been. It’s micro-philanthropy — just people who want to give.”
Karin Jeffers, president and CEO of Clinical & Support Options (CSO), who nominated Miller as a Difference Maker, appreciates how the spirit of the Kind Squad goes well beyond helping others and speaks to the meaning of kindness itself.
“The Kind Squad is built on a simple but powerful mission: to show children and families in need that they matter — and that their community truly cares,” Jeffers said. “The Kind Squad has helped literally thousands of children and families, providing toys, essential items, emotional support, and moments of joy during some of the most difficult times of their lives. Jess leads this work with no expectation of recognition or reward. Her motivation is purely selfless: to make a real difference, one family at a time.”

Long before Jess Miller launched the Kind Squad, she was using her comedy platform to raise funds for nonprofits.
Photo by Bob Zemba, Simple Truth Imaging
Jeffers pointed out the recent toy drive’s haul and its “extraordinary impact” on families. “She ensured that countless kids experienced the magic of the holidays — many for the first time. But Jess’s work goes far beyond gifts. She understands that what families often need most is reassurance: the knowledge that they are not forgotten, that someone sees them, and that kindness still exists. By showing up with compassion, consistency, and heart, Jess delivered something even more meaningful than toys — hope.”
That’s real impact — generated by a true Difference Maker.
Early Stages
Miller’s foray into performing in public didn’t get off to the most auspicious start — she tried out for America’s Got Talent.
“I didn’t do comedy; I sang. And I killed the song. I literally killed it. Not in a good way, but in a very, very bad way,” she recalled. “But I had fun, and I wanted to do that again. I love performing.”
So she took some acting classes — “because I really sucked” — and eventually landed a part in the musical Rent at Exit 7 Theater in Ludlow. She enjoyed that a lot, but had an itch for comedy, so she took a comedy class at Carolines in New York City, then tried some improv in Boston.
Progress was slow — she auditioned for another musical as well, but didn’t get cast — before one of her teachers gave her some advice: “if you want to do comedy and you’re not getting gigs, book yourself — post your own shows.”
So around 2013, Miller produced her first comedy show — a fundraiser for foster kids for the Massachusetts Society for the Prevention of Cruelty to Children (MSPCC). In fact, comedy benefits were the model right from the start — make people laugh, raise money for a good cause.
“Then I started doing monthly performances called the OMG! It’s Only Wednesday comedy show. Every month, we would try to do something to benefit the community. So, if it was bringing a can of food, you’d get five bucks off a ticket. Tickets were already cheap. But bring a coat, bring in hygiene products, you get five dollars off a ticket,” she explained. “I think, when you’re in business, you should be grateful that people support you, and try to give back to your community.”
A few years later, she opened up a venue in downtown Springfield, called the OMG! Comedy Club, that ran into issues with the landlord, and that project eventually shut down. “That was just before COVID, though, which may have been a good thing,” she said.
Which brings her story to 2020, when the Kind Squad — due to that woman reaching out about an unpaid water bill — started to become more than a Facebook page. “It just stacked up from there. We’re close to $300,000 at this point, just doing little missions like that.”
The week before she spoke with BusinessWest, Miller and her team of volunteers had completed a coat collection for a homeless shelter, and they’re constantly receiving other requests from far and wide that the Kind Squad community, currently about 2,700 strong, quickly responds to.
Miller’s wife, Stephanie Greenberg, partially explained why foster kids and foster moms are so important to the nonprofit’s work.
“I think it’s important to be able to give to kids because they don’t have a voice — especially foster kids. I mean, they get nothing. I used to be a teacher, and when they get moved, they just get a trash bag full of whatever they had in their house that they were able to grab at the time. And it’s just sad to see that. So anything we can do to make their lives, especially the holidays, a little happier for them, I think it’s good.”
Kim Dougherty, a volunteer with the Kind Squad, said the model works because each individual commitment is very light — the power is in the accumulation of all those tiny donations.
“It’s not a matter of, ‘oh my God, we need to give 100 bucks.’ You can give $1.25, and if we all give $1.25, look at what we can do. It gets infectious because you want to spread it to everybody else — to say, ‘hey, look at this. It’s minimal; it’s really not a lot.’ How many people can throw a dollar aside? Most of us can. So I think the simplicity of it was what drew me in — it’s not going to take all my time. It’s not going to take a ton of money. It’s simple. And that’s why it works.”
“And if you can’t give a dollar,” Greenberg added, “it’s not a big deal — there are other missions and other ways you can help. Like, for the toy drive, people brought in their gently used Christmas bags, and we can use them next year. That was a game changer.”
Kind Words
Sometimes Miller asks herself a troubling question: “why is it so hard to be kind?” And she realizes that the best way to answer it is, simply, to model kindness, showing others that it’s not that hard after all.
“In 2020, after George Floyd got killed, I was just like, ‘I don’t know what to do.’ Like, on a national or global level, what can one person do? But on a community level, a local level, you can do a lot.”
And some of it goes beyond the micro-philanthropy.
“In addition to toy drives, food drives, and fundraising campaigns to help families in need, Jess and Steph and the Kind Squad have helped families dealing with children diagnosed and going through treatment for cancer, using her Kind Squad page to gather emotional support, physical donations, and volunteers to support the family and visit them in hospitals,” Jeffers noted in her nomination.
“Jess has an exceptional ability to mobilize generosity and unite people around kindness,” she added. “She pours her time, creativity, and personal energy into the Kind Squad, building trust with families and inspiring others to give, volunteer, and care. Her leadership has created a ripple effect that continues to strengthen the community long after any single event ends.”
“I post it, and then people donate, and if we can get enough money, then the mission is completed — and we do that over and over and over again. But it never comes from me. It’s always from the Kind Squad.”
Amid the surprising success of December’s toy drive, Miller teamed up with organizations like the MSPCC’s Kids Net program, CSO, the Massachusetts Department of Children and Families, and others — “basically, we partner with whoever needs toys.”
And now, she’s thinking bigger. “If I can get the systems in place the right way, I have an idea for the Great American Toy Drive, which is all of America, all helping foster kids. It’s either me going on tour or getting at least 50 other comics involved from all 50 states, and then doing the toy drive on one night.”
She then looked around at the small, rented office in downtown Chicopee that the nonprofit calls home, and thought about the long week spent moving $100,000 worth of toys to people and organizations in need.
“If I have my own space, then I’ll be able to do a lot more. This is not big enough for us to do $100,000 worth of toys. But we have to stay small until we can afford it — because we really haven’t done a lot in terms of income. It’s mostly small grants. They’re not even grants, just very small donations to get us through. In 2024, it was tough because the focus went from helping people to paying for the space. I’m like, ‘this doesn’t feel right.’”
But since then, the volunteers — a core team of eight, plus about 30 who help with the toy drive — have eased the load significantly, allowing Miller to dream of what might be next in her mission of kindness.
“I don’t know what I’m doing. I have no clue. I jump in and I’m like, ‘I’ll figure it out,’” she told BusinessWest. “I post it, and then people donate, and if we can get enough money, then the mission is completed — and we do that over and over and over again. But it never comes from me. It’s always from the Kind Squad.”
Still, it’s gratifying to be called a Difference Maker.
“I like to make a difference. I want to make a difference,” she said. “I guess that’s what I’m getting at. I think I just want people to know that they’re not alone — and that a lot of people feel the same way. And I’m surrounded by those people. If you’re part of the Kind Squad, that means you have some humanity in you, and you care what’s happening in the world.”














