Type Faces: Meet Bill Connolly.

Welcome to our Type Faces series, where we’ll be sharing the stories of some of the fabulous people behind the type here at Monotype. From all around the globe and across the organization, our Monotype colleagues truly prove that, like Charles Nix, Senior Executive Creative Director at Monotype, always says, “We are ALL creative.”

Bill Connolly is a comedian, writer, and all-around creative connector. His unique blend of storytelling and strategy led him to Monotype, where he now serves as Head of Customer Engagement for Strategic Accounts. Read on to learn more about Bill.

Bill Connolly hosting Brand Talks in Chicago.

How does creativity show up in your life?
I’ve been performing improv and sketch comedy for more than 15 years. I got my start in Boston, then moved to New York and LA to study and perform at places like the Upright Citizens Brigade, the Groundlings, and Second City.

Bill and his comedy partner, Erin Berry, produced a series of shows at the Comedy Central Stage in Hollywood.

I also write. I’ve published three books, I co-write screenplays, and I keep a newsletter on Substack called The Renaissance Plan. I also have a column at Rolling Stone Culture Council.

One of my favorite quotes about comedy is: “The job of a comedian is to lead an interesting life and share it with others on stage.” I’ve always tried to live by that.

Performing in a character showcase at Westside Comedy Theater in Santa Monica, CA. 

That’s a great quote. What are some of those interesting experiences you’ve had?
I’ve always said yes to opportunities that make me a little uncomfortable. Over time, that’s made me pretty hard to rattle. I’ve spoken at Brand Talks and South by Southwest, and I’ve emceed events for Monotype. I always joke that because I’m a failed comedian, I make a pretty good emcee. If you’ve bombed on stage before, you just don’t get spooked.

Bill speaking at an event hosted by the Data Vandals in partnership with Canva in East Village, NYC.

A few specific experiences come to mind. I once got booked to do a show in a tavern in Joshua Tree with friends, and we were put up in this house in the desert. It felt like we were totally alone, like nobody lived there, and I didn’t expect anyone to show up to the show. Then, the whole region turned out for it, out of nowhere! 

I also auditioned for America’s Got Talent — turns out improv doesn’t translate well there. I won a dance competition on The Ellen DeGeneres Show. And I once got paid to be an audience member on The Bill Cunningham Show, where I was asked to give really dramatic reactions for the camera.

Preparing to audition for America’s Got Talent.

You mentioned you’ve written three books. What was the story behind that?
I set a goal to write three books before I turned 30, and to write one in every city I lived in. I missed the age cutoff by a few months, but I got it done.

In Boston, when I started performing comedy, I quickly realized that there was such transferability in the skills needed on stage and skills needed in the business world. At the time I also hosted an internet radio show, kind of an early podcast, called “Funny Business.” That became my first book.

In New York City, where I moved to be closer to my now-wife (and also to pursue comedy), I wrote The Success Disconnect. That book really explored the complexity of success-pathing, that is, trying to build a career that maps to your internal ideals. I proposed to my wife with this book, by dedicating it to “my fiancée” and asking her to read it at the book launch party.

Bill and his wife Colleen, on the night of their engagement.

In Los Angeles, I focused more on entertainment. I wrote Mindspace while I was performing regularly and pitching scripts. You are immersed with people chasing their dreams in that city, which is very inspiring creatively.

Bill and his fellow performers at the Hollywood Fringe Festival.

I’m fascinated by how different places shape our thinking. I’d love to explore that more, maybe in a future project.

What inspires you creatively?
People. Relationships. I like to collect connections with interesting people — people from different disciplines, backgrounds, and perspectives. I get so much energy from hearing how others approach their work.

I’m also drawn to creative spaces where people can share ideas. That’s a big part of why I enjoy hosting events. When you bring designers, musicians, screenwriters, and strategists together, the conversations are electric.

I’m inspired by people who make things because I think there’s a vulnerability in it. You’re putting yourself, your own identity into the output, and that takes courage. 

What else do you collect, besides relationships?
Lately, art. I’ve started picking up small pieces in my travels — nothing expensive, but always something meaningful. 

My wife worked for a photographer and acquired this beautiful photo of Whitehaven Beach in Australia. We had it hanging in our bedroom long before we actually visited, just because it was a beautiful image. Then I brought my wife with me on a Monotype trip to visit the Canva HQ, and we ended up having a picnic on that same beach.

Bill and Colleen on their way to Whitehaven (in style).

Now the photo means so much more. I love how art can capture a place and then take on new meaning over time.

How does creativity show up for you at work?
I lead strategic engagement with some of our largest partners. That means helping them think through how type can support their business goals and brand expression. But I’ve been at Monotype for ten years, and I’ve had the chance to work in PR, content strategy, partnerships, and marketing. I’ve had four or five careers here. That’s why I’ve stayed.

What I love most is the exposure to creative people, to builders. One day I’m talking to a creative director at a global entertainment brand, the next I’m chatting with a small foundry or a musician. It’s incredible how many people are connected by type, and how many different ways type shows up in the world.

What are some highlights of your time at Monotype?
Helping Monotype show up in creative spaces has been really meaningful to me. We’ve been part of tentpole events like Cannes Lions, SXSW, and Web Summit. 

Bill (at left), Charles Nix (at right), Francesco Maselli (at center), and the winners of the Young Lions competition that Monotype sponsored in Cannes.

We launched a typography curriculum with Canva for 60 million education users. And we even experimented with a Helvetica NFT. I love that this work keeps evolving.

Typography is a gateway. It touches everything, from brand to culture to identity.

SXSW in Austin, TX in 2024.

Do you have a favorite font?
I’d have to go with Courier, because I am a writer and it’s the typeface used in scriptwriting — so I’ve seen it quite a lot during some of my most creative and fun experiences!

As someone who appreciates the creative process, what creative work do you recommend?
I love content that is original, that makes something out of nothing. Books like Big Magic by Elizabeth Gilbert and On Writing by Stephen King explore that ideal and always get me motivated. Gary Gulman is a comedian I admire. And the Conan O’Brien Needs a Friend podcast is a favorite. I just love hearing how people think and create.

What might surprise people about you?
I’m a confident speaker, but I’ve always battled anxiety. I’m definitely my own worst critic. After most conversations, I replay them in my head wondering what I said wrong. But I’ve learned that our imperfections are what bring us closer to people. That’s something I really believe. We are all just doing our best!