Cassidy Priester, Director of Development at Canterbury Shaker Village, loves hearing how your weekend went.
Usually, its the first thing she’ll ask you about on Monday (before she’s even put her stuff down), intently listening to your restaurant or movie reviews. Other times, it’s deep in the week, and she’s so sorry to have not asked how your mom’s visit went, right as you are walking into a meeting. But each time, she’s seriously enthusiastic about wanting to know what you have going on in your life, who do you like to have fun with, and how do you like to create meaningful experiences for yourself.
It’s that kind-hearted, curious charisma that’s at the essence of how Priester operates as Director of Development, where she is tasked with cultivating a community of supporters who can give financially towards Canterbury Shaker Village’s annual funding and preservation projects. Prior to joining the nonprofit’s staff in July of 2025, Priester served as the Deputy Finance Director for Governor Charlie Baker’s re-election campaign and Director of Development for The BASE.
At the museum, annual fundraising is a pivotal objective that hinges on delicately balancing funding streams and donor relationships. For most, asking for money can feel pressurized and performative, but Priester focuses on the shared purpose that comes from connecting people to the broader mission and magic of the Village.
“We all want the Village to thrive and succeed, and we each have something to bring to the table. For me, it’s my full-time responsibility to create moments for folks to fall in love with this place. For others, they have the capacity to transform and sustain our future through giving. We’re working together,” said Priester in a recent conversation.
As Canterbury Shaker Village enters an active time for fundraising, Cassidy Priester shares her developmental principles and current fundraising priorities with Manager of Communications Garrett Bethmann.
This interview has been edited for length and clarity.
You’ve worked on political campaigns, for youth organizations, and now at a museum. Fundraising is important for each of those nonprofit sectors, and each has a slightly different methodology. What type of fundraising skills have you picked up across these roles?
Campaigns are fundraising machines. I worked for the most successful gubernatorial fundraising operation in history. There, I learned a lot of the operational skills. Sometimes we were doing ten events a week and processing hundreds of gifts in a single day. With scrutinizing campaign oversight, it was critical that we had seamless operations and recordkeeping. But with so much volume, and the transactional nature of political giving, I didn’t get much of the “real” fundraising experience until I went to work for a youth development nonprofit.
There is where I learned that people give to people. I learned how amazing it felt to be part of a tight-knit community, passionate about the same thing. And I learned that the work is so much more than fundraising appeals and acknowledgement letters. You need to inspire people to care as much as you do and show them how an investment will make a meaningful difference.
So political fundraising taught me to use my brain. Working for a youth development organization taught me to lead with my heart. And now at the Village, I’m doing both.
We have professional operations, a strong staff, and a committed board. I have mentors and folks investing in my own professional development. I still suffer from imposter syndrome and sometimes can’t believe the faith that’s been placed in me. All I can do is remind myself to put my best foot forward every day knowing that there’s an actual village of people who have my back. We all want to see this place succeed!
Are there any principles that you’ve found grounding in how you approach cultivating donor relationships?
There are a lot of buzzwords in professional development around fundraising. You need to be “relationship-based” and “authentic.” Sometimes talking in these terms can feel a little performative, though. Of course you want to have authentic relationships with folks! Those are the relationships that mean the most to us in our personal lives, so why should it be any different in your professional life?
I enjoy building community with people. When I ask someone about their family or how their last vacation was, it’s not because I’m checking a box on my list of donor cultivation steps. I really do want to know about your daughter’s first semester of college or the best Mai Thai you’ve ever had in your life in Tahiti. I want to send handwritten cards expressing thanks or make a phone call to tell you about something that just made me think of you. In that way, I have the best job in the world. I’m making friends who also care about the Village as much as I do.
And that’s the heart of it. I’m reframing the narrative around fundraising. We all want the Village to thrive and succeed, and we each have something to bring to the table. For me, it’s my full-time responsibility to create moments for folks to fall in love with this place. For others, they have the capacity to transform and sustain our future through giving. We’re working together! And when you look at it like that, there’s less apprehension when talking about money. We are all giving to the Village even if it looks different.
What are your current development priorities for the Village?
Most urgently, we need to raise our final $360,000 to preserve the Shaker Infirmary to match our Save America’s Treasures challenge grant. The Infirmary is a spectacular building with so many stories to tell about women in medicine, cutting-edge advancements in technology, and treating our elderly with compassion and dignity. This history is fundamental in our understanding of the Shaker community at Canterbury and its outsized impact on the broader American society.
The preservation project will begin in the spring, so we need to raise these funds now. We’ll use our Giving Tuesday campaign to help raise awareness for this project and will need major donor support to get to the finish line.
Just last week, we had a trustee put up a major challenge. When we raise $235,000, they will contribute the final $125,000 to bring us across the finish line. That put some wind in our sails!
Can you speak to a fundraising moment or event since you began, encapsulating the challenge, success, and outlook for development at Canterbury Shaker Village?
Our annual Simply Shaker dinner was a highlight this year. I’ve hosted a lot of fundraising events, and none of them felt anything like Simply Shaker. Our whole team pitched in, so even before the event, it felt good to be in the trenches together. When you know almost every guest, it really does feel like a party! The Village is a stunning place to gather and the food was delicious (no rubber chicken on Erin’s watch). Every detail was thoughtful – just like you would do if you were hosting at your own home. We took a lot of pride in the event.
And we had a record-breaking night of fundraising! A trustee put up a huge matching gift, which excited several other trustees to make their own. In the room, nearly everyone made a gift, from $25 to over $10,000! The size of the gifts mattered less to me. It was that everyone felt so good to be part of this community that they wanted to be part of the giving.
We raised funds for several capital projects, like painting the North Shop and our preservation internship program, and updated folks this fall on how we succeeded in completing those projects. We’re showing the impact of our fundraising and building trust with our donor community.
Fundraising is always going to be a challenge, especially with all the economic uncertainty now. But we’re showing there is a right way to do it. We’re bringing people together in community around something we all care about. This was just one night, but it proved that the Village has a bright future with so many amazing people standing behind it.
If you would like to make a gift to Canterbury Shaker Village, please make a gift here. If you would like to connect with Cassidy Priester regarding fundraising at Canterbury Shaker Village, please email here at cpriester@shakers.org. Sign up for the newsletter to stay connected.
