Jennifer Ryan,
Board Vice President,
South Portland Little League
How she uses Cheddar Up
- Concessions
- Sponsorships and donations
- Raffle ticket sales
- Fundraising event payments
Cheddar Up user since
April, 2023
NUMBER OF COLLECTIONS
7
TOTAL COLLECTED
23K+
(and counting!)
From Paper Checks to Digital Ease
For Jennifer Ryan, Vice President of South Portland Little League, modernizing how the league handled money wasn’t just about convenience-it was a necessary step to keep up with changing habits. Parents no longer carry cash like they used to, especially when they’re dashing to and from the ballfield. That’s where Cheddar Up came in.
The league’s first major success with Cheddar Up was the introduction of $10 concession punch cards. With a simple QR code at the concession window, families could scan, pay via card, and receive a punchable paper card their kids could use throughout the season. Whether it was for a post-game Gatorade or a quick snack during double-headers, it created a fast, flexible way for families to pay without relying on cash.
“We don’t have a POS at concessions, so the punch cards let us offer card payments without needing extra tech. Families loved it.”
Jennifer Ryan,
Board Vice President, South Portland Little League
This small shift made a big impact. It allowed the league to collect thousands of dollars electronically; no iPads, POS systems, or Square accounts needed. Volunteers didn’t have to handle or deposit as much physical money, and families appreciated having the option to pay how they prefer.
Sponsorships and Raffles Go Digital
Every season, the league taps local businesses for sponsorships to help fund equipment, field upkeep, and programming. In the past, this meant a lot of back-and-forth to collect paper checks. With Cheddar Up, those businesses can now pay digitally in just a few clicks. Jennifer set up a collection page that includes different sponsorship levels, each with a description of what’s included.
That feature proved especially helpful when one level sold out. Jennifer could simply toggle off that option while keeping the rest of the page live. No need to rebuild or relaunch anything. This flexibility has made it easier to manage demand, communicate clearly with sponsors, and avoid administrative headaches.
The league also expanded its use of Cheddar Up to include key fundraisers. Their March Madness-style event, “Bats, Balls, and Brackets,” brought in extra donations, while the annual calendar raffle fundraiser used QR codes and links so kids could share with friends and family beyond their neighborhood. Digital tools meant grandma in another state could support her grandkid’s team without needing a paper ticket.
“Sponsors love not having to drop off checks, and families can sell raffle tickets using links or QR codes, even to out-of-town relatives.”
Jennifer Ryan,
Board Vice President, South Portland Little League
“Any time we can collect money electronically instead of physically, it just cuts down on the risk and makes life easier.”
Jennifer Ryan,
Board Vice President, South Portland Little League
Bigger Reach, Less Risk
The benefits of Cheddar Up went well beyond payment convenience. Reducing the amount of cash exchanged on-site made a huge difference in risk and volunteer workload. With over $3,000 in digital concession card sales alone, the league saw fewer trips to the bank and less time spent counting bills. It also meant fewer worries about kids or parents carrying around envelopes full of cash during fundraisers.
Beyond simplifying money matters, Cheddar Up helped families and volunteers promote fundraising efforts in smarter ways. Whether through social media shares, email links, or QR flyers, the digital access opened doors to new supporters. According to Jennifer, the reporting features also earned high marks. Exporting payment data made it easier to reconcile funds and keep the sponsorship director and treasurer on the same page.
And while she spends most of her time behind the scenes, Jennifer says the tech helped everyone feel more empowered. Especially when it came to contributing to the community’s beloved youth league. “It’s all rewarding,” she said. “It’s about the kids, their experience, and creating something lasting for our community.”
Before you go
Want to see how Cheddar Up can help your organization the same way it did for South Portland Little League? Get started today!
