NYWIFT Blog

By Paige Hapeman

Everyone please take a moment to welcome our new NYWIFT Member, Leslie Cunningham!

Leslie is a director, writer, and producer with experience spanning documentary, branded, podcast, narrative, and digital video. She is a Supervising Producer and Head of Branded Content at the NYC-based creative agency Diagonal Media. She approaches storytelling as a writer first, understanding the central “why” of a story to unveil the universal truths that create compelling and authentic narratives.

She was recently featured as a panelist at the NYWIFT FinanceHER Institute at The New School in September 2024, discussing all things branded content. 

Continue reading on to learn more about Leslie!

NYWIFT New Member Leslie Cunningham

Tell us about your journey to becoming a director, writer, and producer.

I started at the production company, Born in Brooklyn (BIB) Media, where I worked alongside two incredible filmmakers, Joe Mauceri and Kenton Young. I was at BIB for four years where I learned everything from cinematography, audio, and lighting to story producing, editing, and the ins and outs of running a small business.

From BIB I went to the production company Embassy Row, where I worked as a digital video and podcast producer with their digital team. My background as a camera op, producer, and editor was a great asset here as this was a small team and I was able to manage all things pre through post-production for their digital video team. It was also an opportunity to hone my writing skills, as some of the shows had a more narrative arc. During this time, I also wrote my first short story, “Nobody is Happy in Kentown, Missouri,” and self-published on Amazon.

I am now at Diagonal Media, where I really stepped into directing. Diagonal is a very encouraging and creative environment, where I’ve been able to execute my creative vision and hone my directing style while launching new initiatives like our branded content push.

Leslie working on set

You are a Supervising Producer and Head of Branded Content for Diagonal Media. How did you come to work with this organization and how has your experience been?

I came to work with Diagonal Media through a freelance opportunity via the Media Mavens Google Group — another great resource for women in the industry. I’ve been with the organization for about two and a half years, and it’s been an incredible journey.

I started as a producer and editor before moving into a supervising producer role. Last year, I approached our CEO, Blake and COO, Garrett about starting a branded content team and moving the company towards more commercial, branded documentary and branded narrative work. They were all about it and at the beginning of this year my colleague, Alex Tragellis and I kicked it into gear, working with our team to create three spec commercials. We have exciting pieces in development and can’t wait to see what doors open for the rest of 2024.

Also, I have to give a special shout out to Diagonal Media for being a very kind, authentic and balanced place to work. This is a company that is really all about its people, prioritizing our mental health and our time, allowing us a space to be creative and make really meaningful work. We also give back to the NYC community. We are majority LGBTQ+ owned and we do some pro-bono work with the LGBTQ+ community, and NYC community at large through our DGNL Gives Back program.

You are currently working on your first full-length novel. How is this going and what has been the most rewarding part so far?

I am excited, nervous, and eager to finish my first novel! The working title is What Happened to Jeff?

Writing for videos has been a fulfilling part of my creative career, but writing fiction is a new challenge, and one I’ve been completely engrossed in. I try to allocate two hours every morning to write. Some days are more successful than others, but the opportunity to live fully in my creative brain while structuring a story around the pillars of fiction storytelling has really snowballed into my creative work outside of novel writing.

Even if it’s just a page, getting something new on paper that wasn’t there before feels like a huge success. I have been working on this novel for about two years now, and when it’s finished, I won’t go back to a time when I’m not writing fiction every day. It has been that meaningful to my life, I need it.

Leslie working on location

You work with commercial, documentary, and narrative content. What is the most exciting element of working with each of these different types of media and how do they differ from each other?

We recently launched our branded content initiative at Diagonal Media. My colleague, Alex Tragellis and I co-lead that department. Branded content is a very competitive and creative space, which makes it fun to work in. Brands are constantly pushing the envelope, trying to get eyeballs, and move quickly. I like the challenge to stretch creatively in this space. Our branded content team is very new, and we are working on spec commercials for brands we admire now, which allows a lot of room for creativity.

I co-directed the documentary short Deserted, about food insecurity in America, which premiered this year. I also had the opportunity to produce the documentary short Breaking the Fourth Wall, about queer censorship around the world, with Diagonal Media, which premiered last year at Lincoln Center during the Criminal Queerness Festival.

I’ve also directed many corporate-backed, doc-style pieces throughout my career. Documentaries are an opportunity to open people’s eyes beyond their day-to-day reality and encourage them to see the world through someone else’s perspective. I suppose this is what all good stories do, but to help someone tell their story in this way is incredibly fulfilling and different from other types of video work.

I have the least amount of experience with narrative content, but the opportunities I’ve had to produce here I have really enjoyed, and I’d like to do more of this work. I appreciate the care put into each frame in narrative filmmaking and working with talented DOPs to make this come to life.

Leslie at the Justice Film Festival

As a director, what types of projects do you seek out and what do you hope audiences take away from the stories you direct?

As a director I want to make more emotionally resonant commercials. I love short, thought-provoking pieces that can shake you in only 15 or 30 seconds. I want audiences to come outside of themselves for a moment and remember the things we all have in common — love, longing, heartbreak, joy, sadness, and fear (now I’m just naming characters in Inside Out 2, but you get it). I want to make things that remind people we’re all human, and we have more in common than we do differences.

Leslie directing on set

What have been the biggest influences and inspirations for your career?

This is like when someone asks you your favorite movie and you draw a blank! It feels like such a big question, but in reality, I think the people who I have had the opportunity to work with on a day-to-day basis inspire me.

At Diagonal Media, we foster an environment where people are encouraged to pursue their creative passions both inside and outside the workplace. My colleague Lillian just wrote the play Primordial about pregnancy and childbirth which rocked me, it’s such a powerful piece of art. My friend Tyler is a very talented DOP who is constantly sharing these crazy visuals and experimenting with color and light. My colleague Alex and my brother Aaron are both stand-up comedians.

Check out some of Leslie’s work and keep up with her on her website. Follow her on LinkedIn and Instagram.