Shayna Sherwood

39 | Casting Director, Realtor, Co-Teacher, Sherwood Real Estate, Doro/Sherwood Casting, FNESU
Residence: Franklin

Career Highlights: The career highlight I’m most proud of is landing an internship at Fox Television during the golden age of network TV, when Bones, Glee, and American Idol ruled primetime. It was an incredible time to learn the business from the inside out. I learned from every single meeting, every script, every interaction. I still remember what my boss drank, a non-fat double decaf cappuccino, that I proudly got her every afternoon. I’ve always found each moment to be an opportunity to learn and grow. That experience gave me the grounding, broad knowledge, and confidence that propelled me forward.

Community Involvement: My community involvement includes supporting various organizations within the performing arts sector, but if a cause needs a hand and it resonates with me, I’m all in! From student productions, to lending a hand to a family directly in need. I believe in showing up for my community when it matters most, even if the cause does not directly effect me.

I currently serve on…

-The Board of Directors for the Friends of the Opera House in Enosburg Falls. (The Opera House is a historic center for the presentation and promotion of the performing arts and activities that celebrate our sense of community).

-The Advisory Board to the Vermont Production Collective (VPC is a 501(c)(3) non-profit  established in 2021 by working professionals, to support established and aspiring artists in film production and related fields. We exist to facilitate collaboration, mentorships, networking, and more).

-The Town of Berkshire’s Planning Commission

And a number of other small community organizations and events as they arise.

What motivated you to live and work in Vermont: I was motivated to live and work in Vermont because this is my home. I’m a proud, born-and-raised Vermonter who grew up attending Rainbow Mountain Preschool, Berkshire Elementary, and Enosburg Falls High School. I learned to dance, sing, and dream in this beautiful state. A career in the entertainment industry took me beyond our borders, but those experiences gave me the tools and perspective to return home stronger. Now, I’m committed to continuing my career here, using what I’ve learned to help grow and celebrate Vermont’s creative community.

Favorite part of your job: My favorite part of my job as a Casting Director is connecting with actors, being a small part of their creative journey, cheering them on, and watching their paths unfold in amazing ways.

My favorite part of being a Realtor is connecting people to place. I get to help families not only find a “home,” but find their place, and supporting sellers as they move forward onto their next journey. Every match strengthens the community I love and allows me to be a pivotal part of how our community is shaped.

My favorite part of teaching is the students! They’re curious, bold, and not afraid to test you. Once you’ve earned their trust, real magic happens and you get to learn and grow from each other.

Most inspiring mentor and why: My most inspiring mentor is my mother, Margo Sherwood, the first female fashion buyer for Sears Canada in the 1960s. From launching Sherwood Fabrics and Bell Bottoms by Margo in Montreal to opening restaurants, antique shops, and Sherwood Real Estate in Vermont, she’s built a lifetime of fearless creativity and entrepreneurship. At 80 years old, she’s still unstoppable! She is stylish, innovative, and an absolute delight to be around.

What is the best career advice: The best career advice I have received is to slow down, double-check what you’re doing, and really think through the possible outcomes. Teamwork makes the dream work, and the magic happens when you’re not afraid to collaborate and think outside the box!

What would most people be surprised to learn about you: Few people know that I’ve always secretly wanted to compete in a demolition derby!

Favorite Vermont escape: My favorite Vermont escape is any mountain hike that leads to swimming.

Favorite Vermont season: My favorite Vermont season is Fall. It is the most magical time of the year!

If you had unlimited access to funds, which cause(s) would you support: The cause I would support if money were no object is addressing the substance abuse crisis affecting our state and my own community. Friends I grew up with, people I’ve known since elementary school, need our help. I would build a dedicated space in every single town, a safe place where people can find help, understanding, and connection. It’s an incredibly complex issue, but I believe it’s at the root of so many other challenges that our state faces.

Where do you see yourself professionally in the next 5-10 years: In the next 5–10 years, I want to have multiple large-budget, Vermont-themed films in production and others continuously in development, all part of building a truly functioning entertainment industry in our state. I want to share my home and land with others as they visit VT, showing off its beauty and creative potential. Most importantly, I want to inspire the youth of VT to dream big…to know they can go anywhere, be anything, and do whatever they set their minds to!

Drawing on your experiences, what advice would you give to someone looking to get involved in community service: Empathy goes a long way. Truly envisioning yourself in someone’s shoes opens a world of opportunity. Don’t be afraid to ask questions or offer help, even if it isn’t accepted the first time. A friendly smile can also make a huge impact.