Hamilton Chicago’s Associate Company Manager Dishes on her Path From the Stage to an Office

Full disclosure: After interviewing Kaitlin Fine, associate company manager of Hamilton Chicago, I may or may not have asked my coworkers how weird it would be (on a scale of 1-10) to call her up and ask if we could be best friends. Because when I “meet” someone as down-to-earth, driven, and smart as this lady, that’s where my mind goes. So, allow me to introduce you to my new BFF (she doesn’t know that yet, but just go with me here).

After first graduating from Northwestern with a bachelor of science in theatre (yes, really), Kaitlin realized during her senior showcase that she would rather be behind the scenes than on the stage. That uncanny ability to shift gears and roll with the punches is clearly key to her success; we can’t help but love (and laugh) when she says “nothing is permanent except a baby.”

Here, she discusses what it’s like to be part of a major phenomenon, her thoughts on performing again, and the best way to get your foot in the door to company management.

Name: Kaitlin Fine
Location: Chicago, IL
Age: 28
Current title/company: Associate Company Manager, Hamilton Chicago

Education: B.S. in Theatre from Northwestern University

You started out as a musical theater major at Northwestern. During your senior year, you realized that performing wasn’t what you ultimately wanted to do with your career. How did you come to that realization? Was there any resistance to facing that reality when you had put so much time and work into your craft?
Spring break of senior year, a bunch of the music theatre and acting students go to New York for a showcase—basically a big audition where the casting directors and agents come see you do your thing. After that performance, I was running around the city delivering headshots to those who requested them and found myself standing outside a casting director’s door waiting for someone to open it, shoot their hand out to to take my folder, then close it again. I had this very clear “aha!” moment where I thought to myself, “I’d much rather be on the other side of that door.” It was simultaneously wholly terrifying and remarkably relieving—the latter of which made me take note. It felt…right, if very surreal—I had been performing for two-thirds of my life at this point. My strongest memory is how nervous I was to tell my parents—they had spent so much time and money supporting me and I didn’t want to let them down. Thankfully, they are literally the best humans and just shifted their support to this new direction.

After you realized you wanted to go down a different career path, what was your next step?
 Did you always know that you wanted to remain in theater, or did you ever consider moving into another industry entirely?
I felt very lucky to not have to look outside the industry for other career options, because there was such such a wide range of things I had left to learn within it. Part of the reason I went to Northwestern is because it’s a great school first, and a great theatre program second. I describe it as a “choose-your-own-adventure” program, in both classes and, maybe more importantly, extra-curricular activities. That freedom allowed me to discover my other interests. When I got to school, I knew very little about what went into putting a show up, and by the end of my freshman year I was producing the first ever all-freshman musical. I spent the next four years continuing to work in the massive student theatre scene at NU while performing, so by the time I made my choice to switch, it was much more of a slight perspective shift than a total 360.

What did you learn during your first internship with The Producing Office (TPO)? Did anything surprise you about what interested or resonated with you?
For a second I debated just saying “all the things” here and leaving it at that. My time at TPO was my version of grad school. I learned the players, I learned the game, I learned what I wanted to do, and I definitely learned what I didn’t want to do. There are a bunch of theatre management undergrad programs popping up now, but when I was in school there was nothing, so I really had no idea what to expect.

I found myself standing outside a casting director’s door waiting for someone to open it, shoot their hand out to take my folder, then close it again. I had this very clear ‘aha!’ moment where I thought to myself “I’d much rather be on the other side of that door.”

What I found was that my experiences in college had prepared me better than I thought. I always tell students that Broadway is just like student theatre, but with more zeros, and I really think it’s true! There are the same stressors at any level, and really it all comes down to the interpersonal relationships. It also didn’t hurt that in my first few months there I worked on Rent, Avenue Q, In the Heights, and the revival of one of my all-time favs Ragtime. It made running around midtown Manhattan in the rain (because wasn’t it always raining?) a little more bearable.

What made you ultimately feel at home in company management? Do you find that your background in performing helps you be more successful in this role?
Company management is the best of both worlds to me. I like working in an office— like numbers and logistics and spreadsheets—but I also love the community of being in a theatre. Commercial theatre company management really only exists in New York, so I just had no concept of what it was until I was in the office. Very early on I remember thinking that it seemed to combine my skills and interests more than anything else I had found before, and so far I think I was right.

I joke about my performing past, but in all seriousness, I think it has helped me in every aspect of my life. From the understanding of rejection to the people skills to the ability to project my voice (which I now primarily use to cheer for the Cubs), I think everyone would benefit from an acting class or two.

Photo by Justin Barbin

Before Hamilton, the first show you helped manage was The Last Ship. Tell us about that. What did you learn during that first experience? 
You’d be hard pressed to find more polar opposite experiences than The Last Ship and Hamilton. Obviously the ship did not sail quite as we all expected (it ran for about 12 weeks on Broadway), which was challenging and difficult and, more than anything else, sad. At the end of the day, only about 20-25 percent of shows on Broadway recoup their investment, and I’d say about 40-45 percent of that is a crapshoot. You can have all the right pieces in place, but if it doesn’t catch on, it doesn’t catch on. It’s not a testament to those pieces themselves or how hard they all worked, it’s a testament to the industry itself—it’s subjective and risky and emotional and thrilling and torturous. It was not an easy experience for anyone, but I’m so happy to have had it before working on such a juggernaut. It really helped to keep things in perspective.

At the end of the day, only about 20-25 percent of shows on Broadway recoup their investment, and I’d say about 40-45 percent of that is a crapshoot. You can have all the right pieces in place, but if it doesn’t catch on, it doesn’t catch on.

Let’s delve further into company management and what it means. Give us an overview of what is expected of you, and what kind of skills are required to get your foot in the door with this kind of position?
Company management is a weird, catch all position. We’re part HR (we do payroll/benefits), part accountant (we pay the billz), part camp counselor (we plan the parties), part ticket broker (we run the company seats), part therapist (we deal with feelings). We’re the liaison between the producer and the company, and basically run the day to day business of the show. I love it because we’re at the center of all the action in the theatre – most things that happen pass over our desk at some point.

The skill set is vast and specific – people skills are just as important as understanding the numbers which is just as important as organization, etc. On a big musical like Hamilton, there are usually two people in the department – a CM and an associate (that’s me!). It’s a job that you really can only learn by doing, and I have been wildly lucky to learn from some of the best company managers in the biz.

As far as getting a foot in the door, I think the only way to do it is to dive in. Get an internship, talk to people, create relationships and go from there. In terms of the nitty gritty – once you’re on a show, you may have the opportunity to join the union, ATPAM (the Association of Theatrical Press Agents and Managers) by taking this intense test on all the different union rules. Suffice it to say it’s a bonding experience to study and freak out with the other members of your “class” (aka a group of a dozen type-A 20-somethings) and then you take the test and you pass and then you go get a cocktail.

These days we can find you on the production team of that musical no one can stop talking about: Hamilton. What has been like to be part of such a phenomenon?
I get this question a lot and I have yet to figure out how to answer it. The last year and a half of my life has been grueling, challenging, and thrilling. It has been the definition of once in a lifetime, and I will forever be grateful for this experience. Part of what makes it so crazy is that inside the building, we’re just doing the same thing every other show is doing—putting up the show eight times per week. But what makes this so wonderful/overwhelming/all the things is what happens after you step outside. It’s the 3,000 people at the lottery, the thousands of NYC Public School kids (soon to be nationwide!) studying the show in class to prepare to come to one of our student matinees, Hillary Clinton quoting the show in her convention speech—these are the things that still make me go “WHAT?!” So, I don’t know that I’ll ever find a satisfying answer to this question, but I will end up with a long “Things-That-Make-Me-Go-WHAT?!” list.

Oh, and hands down the best part of this experience has been the people I’ve crossed paths with (including former Everygirl feature Pantea Faed!). I have a whole new community of humans in similar positions in different fields—brilliant, wonderful people I never would have met without the Hamilton hook up. That has been the biggest of all the wins. Cause, let’s face it, as cool as it was to see Beyoncé up close and personal, nary is she going to be a lifelong gal pal.

It’s easy to get caught up in every decision being The Defining Decision of Your Whole Life, especially in your early 20s. I found (and still find) it so comforting to keep in mind that everything and anything can shift.

What does a typical workday look like for you?
In New York, we work out of an office during the day, then go to the theatre each night to check in and sign a box office statement. Here, our office is in the theatre, so we keep more theatre hours. I usually get up, check emails, and do some work from home, clean up my perpetually disastrous apartment, then head to work in the afternoon. Depending on the day, we’ll be in the office at least through the beginning of the show, and often to the end. Part of the gig is always being available, so I’m rarely completely checked out, but in this day and age it’s easy to be accessible, which allows for some flexibility in terms of the actual hours spent in the office. Shouts to Dropbox!

Where do you ultimately see yourself growing in this field? Where would you like to be in five years? 
I feel very passionately that I never could have imagined that I would be here, so how could I possibly imagine what’s next? To quote my main man A. Ham, there are literally a million things I haven’t done. I’ve been fortunate to be able to say yes to some really amazing opportunities, and I look forward to the time when the next one presents itself.

Do you ever consider or feel pulled to perform in a smaller scale performance or show, outside of your full-time job? 
Oh gosh no; I am SO good with not performing. It never felt like I gave something up, just that I chose a different path. Jonathan Groff talked me into singing for a #Ham4Ham show last year and, while it was so much fun, I had an EPIC amount of anxiety leading up to the moment. I’m happy to be where I am.

I never could have imagined that I would be here, so how could I possibly imagine what’s next?

Best moment of your career so far?
Not to be a bandwagon-jumper, since I know Lin talked about it in the PBS documentary, but sitting in the East Room of the White House watching Chris Jackson sing “One Last Time” between the portrait of George Washington and President Obama in his last year in office was…magic.

What advice would you give to your 23-year-old self?
My best gal and I have a saying, “nothing is permanent except a baby.” It’s easy to get caught up in every decision being The Defining Decision of Your Whole Life, especially in your early 20s. I found (and still find) it so comforting to keep in mind that everything and anything can shift —it takes the pressure off.

Kaitlin Fine is The Everygirl…

TV show you wish was still on the air?
Friday Night Lights/Sports Night/Parks and Rec (Sorry, I really like television.

Dream role in a musical?
Peggy Schuyler. Not Maria Reynolds though. Just Peggy.

New York or Chicago?
IS THIS A JOKE?! Chicago. It’s all the good parts of New York without the trash on the streets. Plus Kris Bryant’s steely blue eyes.

Favorite Hamilton song?
If I am in the building during “Room Where it Happens,” I am upstairs watching “Room Where it Happens.” But also shouts to “That Would Be Enough” and “Wait For It.”

If you could have lunch with any woman, who would it be and why?
Michelle Obama. She is the best thing that has happened to our country since the Battle of Yorktown.

  • Love this! It’s refreshing to know I shouldn’t freak out about every single decision right now in my early/mid twenties. 🙂 Really enjoyed this interview.

  • Gillian Robins

    As a Stage Manager with a BA in Technical Theatre, this gives me hope that there’s a career option for me without drowning in debt of an MFA program that’s insanely competitive (I’ve also been out of school for a while… not sure a grad program is right for me now). I’d love to pick her brain some more about getting into this field. I didn’t know a career like this existed. It’s like the best of all the worlds!

    • Johanna

      It’s odd you wouldn’t have heard of it during your degree?
      I did a BA in technical theatre as well (in the UK) and we had multiple lectures about all the roles in the theatre and their functions.

      I work full time as a stage manager now, but would definitely consider company management in the future.

      • Gillian Robins

        You would think, but my college had a very small department which was actor-heavy, and I was quite focused creating my own stage management major at the time. We didn’t have a lot of guest lecturers or much in the way of visiting companies for experience and information. I sat on headset once for a local Repertory company, that was it really. This was also almost 13 years ago when I graduated. Maybe things have changed?

        • Johanna

          Oh, I see. Quite different from performing arts institutes in the UK. We did at least three shows a year (you could do more, you just weren’t marked on them) + a placement in our second year as well as guest lectures and so on. We were also quite small (the whole uni only had 800 students).

          But it seems American colleges are a bit more “pick your own adventure” so you have more choice and flexibility and can make it more into your own thing. So I guess it just depends on what you’re after 🙂

  • Alex Porterfield

    This was an AMAZING article, thank you! I just graduated with a BA in Theatre Performance from Fordham University, but after years of internships at talent agencies, casting offices, and production companies, I just can’t seem to get away from the business side of the industry.. So I’ll officially be working at a talent agency in January and couldn’t be more excited for this new adventure!