Jessica Ashleigh Pomeroy (ARAD ’23) recently started a new position as Major Gifts Officer at Park Avenue Armory. We are proud to congratulate her on her achievements following her graduation from ARAD. We are also delighted to catch up with her and learn more about her career path. Read below for the full interview!
Hi Jessica! First of all, can you share a little more about your background and the experiences that have shaped your career path?
Performing arts have always been an important part of my life. I grew up performing in plays and musicals in and around my hometown, and went on to study musical theater for one year at Marymount Manhattan College before transferring to The New School, where I ultimately got my BFA in directing and producing.
After graduating, I did a lot of independent production with friends from school. We produced a site-specific play festival in Brooklyn, a new play reading in lower Manhattan, and several virtual play festivals and events throughout the pandemic. In the Spring of 2021, I co-conceived and produced an online arts experience called Remember Fest 2020 featuring visual and performing art inspired by the experiences of artists during the pandemic. Self-producing really sparked my interest in fundraising. I remember feeling so proud that we were able to raise enough funds to support artists in achieving their visions while bringing meaningful work to audiences.
The impact of the performing arts is incredibly personal to me, and I had also begun to see first-hand how vital adequate funding for this kind of work was. I had a growing desire to advocate for and secure funding for the performing arts at a higher level. This eventually led me to apply for a position at HERE Arts Center as a Development Associate. I had interned at HERE in college, and learned about the opening from an email list that they included all of their past interns on. There, my interest in arts fundraising grew, and I ended up working there over the next few years in a variety of different roles which eventually led to where I am now.
What did your journey look like after graduation? Can you describe the steps you took that led you to your current role?
During the second year of my ARAD degree, I was promoted to Director of Development at HERE, where I worked for several months following graduation. Not long after, I learned about an opening in the development department at Gibney Dance, fundraising for a diverse array of dance and social justice programs. This work was aligned with my belief in the transformative power of art within communities, which is at the heart of my love for this work. I was also seeking an opportunity to expand on my fundraising experience outside of one organization. I applied for the position and with recommendations from previous mentors, ARAD professors, and co-workers, I secured the position of Director of Development at Gibney.
Several years prior, I had worked as a Production Assistant at the Park Avenue Armory, and it was a really amazing experience. I admired so much the way that the Armory worked with artists to achieve their visions by virtually any means necessary. I also wanted to be a part of an organization that worked across artistic disciplines in the way the Armory does, helping to secure vital funding for such a major cultural center in the New York City ecosystem. I always knew that if an opportunity came my way to work with the Armory again, I would take it, so when the Major Gifts Officer position became available, it felt right for so many reasons.
How has your experience at Park Avenue Armory differed from your previous roles?
It is a much larger organization than I’ve ever worked for, so it’s been exciting to get work with and learn from such a large team of highly experienced arts administrators. It’s also a very different organization than the others I’d worked with before; the Armory produces a wide variety of genres and styles encompassing both performing and visual arts featuring artists at various stages of their careers. The diverse range of work they do is a big part of what attracted me.
In my roles at HERE and Gibney, my work was much more all-encompassing. I was managing the development team, overseeing the strategic decisions for the whole department, and collaborating across the individual and institutional giving spaces. At the Armory, I am much more focused on individuals. I work with a specific portfolio of major donors, planning events for them to attend, managing their relationship to the organization, and soliciting gifts.
Were there any specific courses or experiences during your time at ARAD that you found particularly helpful in building the skills needed for your career?
During my second year in the ARAD program, I took a class called Mapping Harlem’s Cultural Organizations. This course significantly broadened my understanding of the diverse range of cultural organizations in New York City, and was very experiential. For example, we took a walking tour of Harlem, visited various arts organizations including The Apollo, and interviewed professionals working in the neighborhood’s cultural sector.This kind of broad knowledge of the sector is so important for anyone working in arts and culture.
I also found the Marketing class that we took to be very beneficial. We learned valuable Excel skills, including helpful formulas and data visualization techniques. We also explored CRM systems, understanding their functionalities and uses. These skills have been incredibly useful; I use both Excel and CRM systems (Tessitura at my current position), on a daily basis as a fundraiser, and I have learned that an arts administrator in any segment of this industry or any department within an organization will use these tools frequently.
As you look back, what would be the most memorable experience at ARAD? Is there anything you wish you had known or done differently during your time at ARAD or in your early career?
I really enjoyed participating in Student Advocates for the Arts (SAA) and I wish that I had the time to be more involved, but working full time while I was in school made it challenging. I would definitely recommend that current students get involved. Advocating for the importance of the arts and finding ways to make the work of ARAD students more visible to the broader TC and CU communities is so important and worthwhile.
My thesis research was also very memorable. It was especially interesting to interview accomplished leaders of arts organizations around the city and gain an inside look into their work. One thing I wish I had done is spend more time prior to my thesis work conducting informational interviews with arts administration professionals. I went into my thesis interviews without much experience in this area, which led me to feel nervous and underprepared at times, no matter how much I ‘prepared’ on paper. I think, in general, and I will say this again and again, talking to people who are doing the work you want to do will always benefit you. Not only might it prepare you more for future interviews, but it will make you more comfortable having professional conversations with people in the industry, which you will only do more of as you progress in your career.
What are your long-term career aspirations, and how do you see your current role contributing to achieving those goals?
In the next five to ten years, I hope to be working in a high-level executive position at an arts institution, participating in advocacy and making decisions that allow the arts to continue thriving and allow artists to make work that brings catharsis, empathy, learning, and beauty into the lives of audiences and participants.
Working at the Armory feels like a really exciting next step toward this dream, and I hope it will be a place I can remain for a long time as I grow in my career. As I said before, I have the opportunity in this role to work with highly experienced arts administrators with a wide variety of experience, many different kinds of artists and genres, and the wide variety of donors that comes with producing such a diverse body of work.
Lastly, what advice do you have for current students and recent graduates regarding job searching, career planning, and networking? Are there any strategies or approaches that you found particularly effective?
At the risk of oversimplifying, I will distill the things that have brought me success so early in my career down to two words: relationships and proactiveness.
One thing that has been really important for me is mentorship. When I was at HERE, I found a mentor in my supervisor, and I later joined the Association of Fundraising Professionals Mentorship Program, which matches emerging fundraisers with more experienced professionals for one-on-one career mentorship. When I say a mentor, I’m talking about someone who has a role or does the kind of work that you aspire to be in or do, who you have a professional and/or personal relationship with, where you can ask them questions about how they got to where they are in their career, brainstorm ideas with them, and ask for advice about how to get to the next step in your own career. For me, these have been women who are a few steps ahead in their career from me, but not so far away that it feels like I can’t quite understand where they are coming from. Of course, this is different for everyone, but that’s what’s worked for me. My relationships with these mentors have helped me to understand what a healthy workplace looks like, brainstorm strategic plans and ideas with people other than my direct co-workers, and grow as a leader and manager of others. When it comes to finding a mentor, I would say don’t be afraid to reach out to people who are doing the kind of work that you want to do, whether that’s on LinkedIn, via email, or by stopping by their office if you already work with them. You will be surprised how many people will respond positively to being taken out for coffee and will be willing to answer your questions. As long as you are respectful of people ‘s time and availability, many are excited to uplift others who want to work in the same career.
I would also add that being proactive is one of the most important skills that has advanced my career. What I mean by “proactive” is taking initiative without being asked, volunteering for projects and events, and sharing ideas in meetings. For those aspiring to managerial or director roles, executives seek individuals who demonstrate a willingness to do whatever it takes to achieve results, while keeping high standards. Be the person who steps up to make sure the job gets done, Even if some of the responsibility falls outside of the bounds of your role. Trust me, it will go a long way.
Arts Administration 
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