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Fundraising Five with Jen Winterfeldt

Jen Winterfeldt describes her experience working with Fox Advancement in her capacity as Keystone Community Services Director of Development & Community Engagement.

Published on

Sep 29, 2022

Written by

Fox Advancement

Keystone Community Services Director of Development & Community Engagement

Interviewed by Whitney Anderson

Describe your role with Keystone. Why are you passionate about Keystone’s work?

I am the Director of Development and Community Engagement at Keystone Community Services, a human services organization based in St. Paul. My work is all centered on deepening people’s investment in our mission either through volunteering, contributing financially, or more generally engaging in our work in the community. My job responsibilities interweave in all program areas at Keystone and require connecting with so many different people so I can truly say in the six years I have held this role, no two days have been the same!

Since 1939, Keystone has been a vital community resource in St. Paul. Keystone’s long history of being a trusted place people turn to when they need support or when they are looking for a way to offer a helping hand to a neighbor is deeply connected to my own personal values. Fundamentally, I believe in everyone’s equitable right to access resources and have opportunities which enable them to live with dignity, hope and build the life they want to live. Keystone’s work is truly centered in community and that commitment to each other and our community lives out in our staff, volunteers, supporters, and participants each and every day. It is that humble philosophy and human-centered approach to all of our work which keeps me passionately committed to Keystone.

How long have you worked with Fox Advancement, and in what capacity? What do you appreciate about your partnership with Fox Advancement?

Keystone has been partnering with Fox Advancement for the last 16 months. We have a small but mighty fundraising team at Keystone. When we knew there were some longer-term fundraising initiatives on our horizon that we needed to embark on to meet some of our growing programmatic needs, we knew we needed help. We were looking for a consultant to truly walk alongside us as we launched a bigger fundraising effort. When we initially met with the team at Fox, we knew we had found our perfect match. Together with the Fox Advancement team, we started out by doing a large community engagement strategic planning process, which incorporated opinions from over 750 people, and helped set our course for the future. We now have a 5-year strategic plan, which was informed by our community, and know what new investments from our community will be required to make these program expansions possible. Fox has been a valuable partner in every step of this work and I am so grateful for their guidance, leadership, and support each and every day.

I appreciate so many things about our partnership with Fox but one of the things I most value is their commitment to walking alongside Keystone. They are so deeply invested in our project, our mission, and they work so hard on our behalf, navigating the twists and turns of our project right alongside us. The staff are warm, dedicated, and sincerely feel like a valuable extension to our Keystone team. They are committed to our success as much as we are!

What do you enjoy most about fundraising? What is an example of a fundraising challenge you’ve faced, and how did you overcome it?

I did not come into this role at Keystone as a fundraiser. Earlier in my career, I had done some development work related to special events and philanthropy work personally for organizations I cared about, but I had not ever considered myself a “fundraiser.” To this day, I can’t say I’d ever call myself a fundraiser but I do enjoy helping people live their values through their own personal philanthropy. I think one of the biggest challenges I’ve faced working in development at Keystone was when we needed to quickly identify new funding sources when we had a sudden and large loss in funding. The lost funding was sizable, unexpected, and it left us feeling unsettled fairly quickly. Losing that resource that had felt so predictable for so long, forced us out of our comfort zone to truly work in partnership with our donors in a way we hadn’t done before. We made ourselves vulnerable, told the truth about what was going on at Keystone, and invited advice from our community. Looking back this seems so simple but at the time it felt very radical to share with donors the difficulties we were facing with this significant budget change. Since that time a few years ago, we have morphed our fundraising philosophy to truly be centered in donor engagement. Donors are the center of our work and now our philanthropy philosophy mirrors that. This shift has made my job easier and in so many more ways more fun. I get the privilege of helping people support their neighbors and strengthen their community. And whenever I feel stuck on a project, I put a donor I know in the center of it, thinking to myself, “What would June want us to do or what does Bob want to hear about” and then my answer is so much clearer.

What is a particularly memorable interaction you’ve had with a donor, board member, or volunteer?

Two years ago, I took a phone call from a donor who had just learned about the option to make a charitable contribution from her IRA. I had not connected personally with her previously but she reached my desk because she was curious if giving from her IRA was a gift we would accept. This donor was so excited about this new charitable option to her. For her, giving from her IRA gave her the ability to give even more to organizations she cared about. I will never forget the enthusiasm in her voice as we talked and she literally ended our call by saying, “I’m so excited about this.” Her enthusiasm for giving was infectious and that brief 10-minute phone call has left a lasting impression on me.

On a personal note: Describe your perfect day from beginning to end!

The pandemic and everything related to it has dialed up the hours I’m spending working these days. But I am a person who always has an itch to travel. I always want to be planning my next vacation so the combination of my longer work hours and our inability to safely travel at this time has me longing for an escape that I often only get from traveling. So, all of this is in my mind as I answer the question to describe my perfect day. For me, my perfect day would begin by waking up in a foreign country or a place I have never been before, traveling with my wife, family or best friends. I’d start by enjoying a cup of coffee and planning my adventures for the day. I like to play a game of tennis or take a walk first thing to stretch my travel legs. Then in my ideal world, I’d spend the day exploring a new place as leisurely as possible – on foot, by bike, in a car/train, or better yet by boat. I like to have a little bit of a plan for each day but to have enough flexibility to be as spontaneous as possible to have time to try the things we only encounter on vacation. Being on or in water is restorative to my soul so if I can be snorkeling, scuba diving, swimming, or just “floating” I am a happy person. I like to round out my travel days with delicious food and drinks, cards games, and conversations with my favorite travel buddies. I look forward to the time I can fearlessly hop on an airplane again and explore a new place when it is safe for us all. Until that time, happy travel-dreaming and adventuring close to home to you all!


If you’re interested in working with Fox Advancement for your grant and/or capital campaign management needs, please reach out to us! 

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