Sarah Boocock Cunningham of Walker-Cunningham Fine Art

  • Photography by: Sarah Winchester Studios
  • Copy by: Elizabeth Fitzgerald

Running your own art gallery is no doubt an admirable undertaking. Running your own gallery inherited from your mentor while raising two young children and making it your personal mission to better an already successful company? Overwhelming for some, but this is how Sarah Cunningham, owner of Boston based Walker-Cunningham Fine Art, spends her days.

Sarah is miles apart from the television representation of a gallery girl. Hardworking and family-oriented (her mother serves as the gallery’s manager), Sarah took over Walker-Cunningham five years ago after her long-time mentor left the business. It was a daunting task, but Sarah took it in stride, growing Walker-Cunningham’s online presence while maintaining its incorporation of consultation services and private collection management. In addition, Sarah, a graduate of both Duke and the Rhode Island School of Design, invokes an acute degree of thoughtfulness in curating the 33-year-old gallery, which specializes in mid-19th and 20th century American paintings.

Here, Sarah offers some insight on how her drive to improve an already reputable gallery took her from assistant to owner in less than ten years.

Full Name: Sarah Boocock Cunningham
Age: 37
Educational background: Duke University, BA majors in Women’s Studies and Psychology with a minor in Art History. Rhode Island School of Design, Master
Current title/company: Owner, Walker-Cunningham Fine Art

What was your first job out of college and how did you land that position?
The first job I had out of college was a summer position with a firm specializing in English-style garden design and maintenance in southern Rhode Island. It was hard work in the hot sun. I learned tons and still love to garden.

When and how did you discover your passion for fine art?
From my parents at a very young age. I have professional artists on both my mother’s and father’s sides—painters, photographers and sculptors—and my aunt (a photographer) and uncle (a painter/etcher) on my dad’s side are veteran antique dealers. We spent lots of time in museums, and I was surrounded by paintings and antiques growing up.

When you were looking for gallery jobs at the beginning of your career, what was important to you and why did you choose to work at Walker Fine Art? 
I think it’s important here to say that I was never actually looking for gallery jobs.  As a 23-year-old, I was exploring ways to stay connected to the art world after leaving a design program in grad school.  Not knowing a thing about what a gallery position would entail or how a gallery worked, I had an informational interview over lunch on Newbury Street with my predecessor.  I highly recommend an informational interview to learn about a profession you know very little about. I learned so much, and it led to an incredible opportunity.  As nervous as I was to make the phone calls to request the interview (it took several calls!), it was well worth it.

What type of art does your gallery specialize in? What’s your clientele like?
Walker-Cunningham Fine Art specializes in American paintings, sculpture and works on paper created from 1850-1950, as well as the work of select contemporary artists.  We are the exclusive agent to Dora Atwater Millikin, an artist living and working in Westport Point, Massachusetts.  The gallery is comprised of two spaces on the second and third floors of a Newbury Street brownstone.  Our clientele ranges from new collectors buying their first pieces to established collectors who are building and growing their art collections.  Aside from individual collectors, our clients also include museums and public and private institutions.

Alfred J. Walker was the founder and previous owner of Walker-Cunningham Fine Art. What was it like taking over the gallery when your mentor retired? How did you adjust to your new position as owner?
Thrill with a healthy dose of trepidation. It was an absolute honor to take on full ownership of the gallery in 2008 when Al retired. We had worked together for eight years prior, and I still count on him as a mentor today, almost five years later.

Did you change the vision or mission of the gallery when you took over?
First, I changed the draperies! But in all seriousness and redecorating aside, we have always endeavored to be a trusted resource to collectors, both new and established, and this goal is as strong as ever today. We are evolving by focusing more on web and online outreach as we experience business in our new economy and the incredible impact we are seeing from digital and social media on the art business.

What do you feel you gain and what do you appreciate about working in a smaller gallery as opposed to a larger gallery?
Both in terms of our staff and our physical size, we are a small operation.  As such, I feel we are very nimble.  We can turn on a dime with our focus if the need arises. And I love the size of our “jewel box” gallery—large enough to hang 50+ paintings salon style (floor to ceiling), small enough to feel like a living room.

How have you managed the ins and outs of running a business? Budgeting, filing taxes, marketing, web development, store planning, etc.?
I have an amazing gallery manager who also happens to be my mother. Ridley (Boocock) is an enormous part of keeping us organized, on task and the gallery looking gorgeous. We are always working together to curate the space. We have worked with the same bookkeeper and accountant for years—they, too, are like family! I have an inventory database integrated with our website designed by Artsystems (based in New York), which we manage in-house. So much goes into running the business—it takes a village!

Take us through your average work day. What does a day in the life of Sarah Cunningham look like?
Arrive at work after getting my son (age five) and daughter (age two) off to school. I spend time on email, catching up on art world news and social media. Much of the day is spent keeping in touch with my clients and colleagues and working to promote our inventory and artists. Our inventory focuses on American paintings 1850-1950 and on the work of Dora Atwater Millikin, our contemporary artist whom I represent exclusively. We are always involved with managing or helping to grow clients’ collections: art acquisitions, appraisals, consulting on framing and restoration needs. These are just a handful of possible items we’re involved in on any given day.

In what ways would you still like to see Walker-Cunningham Fine Art evolve?
We are currently focused on connecting with our clients and potential customers in the digital realm. The art world (like so many things) exists as much online as it does in brick and mortar galleries. A main goal for the future includes building our online presence and giving our clients (both new and established) the feeling that they are connected to us both online and through visits to the gallery.

Why did you dedicate your life to art?
The intensity of emotion that art stirs, the thrill of discovery, the satisfaction of pairing a collector with an amazing piece for their collection, and the promise that each day will create an opportunity to meet a new collector or gain a bit of knowledge—to me, it’s a very alluring mix.

What advice would you have for other aspiring business owners, especially those in the fine arts field?
My maternal grandfather was an entrepreneur whose mantra, borrowed from a Calvin Coolidge quote, was “persistence”—couldn’t agree with him more.

Best moment of your career so far?
The day I was hired to work at the gallery. I was 24 years old. I’ve had so many incredible experiences since and can’t choose just one, so I choose the day that started it all.

What is the most challenging part of what you do?
Like a lot of businesses, mine is all about relationships and building trust. I love this part of what I do for the challenge and the reward.

What is the most rewarding part of owning such an esteemed gallery?
Fundamentally we are connecting people with something that brings joy. Art is such a universal love. Whether it is a private collector finding a great fit for their collection or a museum acquiring work that will be on display for the public to see and appreciate, I find this immensely rewarding.

What is one piece of advice you would offer your 23-year-old self?
When decisions come your way, go with your instincts and follow your heart.


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