10 Years Later: A Conversation

In June 2016, Katherine Fox, Kelly Whalen, Kearney Dewing, Sheila Cooney and Sarah Levine all walked into Prosek Partners as new Apprentices eager to launch a career in financial PR. Now, 10 years later, they’ve grown into leaders across the business, helped expand the firm into new markets, fostered longstanding client relationships and, perhaps most importantly, built lasting friendships together.

To celebrate a decade at Prosek, they reflected on what first drew them to Prosek, the moments that shaped their careers, how the communications industry has evolved over the past decade, and the advice they’d offer the next generation of professionals beginning their own journey.

What drew you to Prosek 10 years ago and what’s keeping you here now?

Katherine: I actually started out as an intern in our Fairfield office, second semester senior year. At the time, I was looking for a communications internship that allowed me to get hands on experience with clients while learning more about the world of PR. As I worked through the internship that semester, I realized that Prosek was exactly the type of firm that I wanted to work at post-graduation, and that the Prosek Apprentice (PA) program was the perfect fit for me. I applied to be a PA in our New York office and never looked back!

The professional development that I received, starting as a PA and continuing throughout my career, is one of the biggest reasons why I’m still here. On top of that, Prosek is what Jen Prosek calls a “friendship factory.” Walking into Prosek 10 years ago, I never imagined that I would meet some of my best friends, but developing relationships with amazing colleagues over the years has also certainly been a highlight of my time at the firm.

Sarah: Ten years ago, I was wrapping up my senior year of college and trying to figure out what came next. While I had completed internships throughout school, working just a few days a week in relatively unstructured environments didn’t leave me feeling fully prepared to step into a career in PR.

As I researched New York-based PR firms, I came across Prosek’s Apprentice program and immediately saw it as the perfect bridge between college and a full-time role. It offered the opportunity to continue learning, while gaining real, hands-on experience, which was exactly what I was looking for.

Like Katherine, that commitment to growth and development is one of the biggest reasons I’ve stayed at Prosek. The firm is constantly investing in its people through training sessions, workshops, and opportunities to learn new skills and explore different areas of the business. Just as importantly, there’s a strong culture of feedback that helps everyone continue to learn, improve, and grow throughout their careers.

And, of course, one of the best parts of the Apprentice Program was the people. I made some great friends during that time, and those relationships have made my experience at Prosek even more rewarding over the years.

Sheila: Prosek’s PA program was exactly the type of entry-level hands-on training that I was looking for as I was preparing to enter the workforce. I already had internship experience and wanted an opportunity to really put the lessons I’d learned from those positions to work. Prosek’s incredible client roster and Jen’s entrepreneurial ethos was what attracted me. Now 10 years later, I’ve seen how entrepreneurialism and good ideas are encouraged and fostered here. I love being surrounded by creative, forward-looking colleagues. Having an incredible team that I love working with is what has made these last 10 years so much fun.

Tell us about a pivotal moment in your career.

Kelly: Moving from the Fairfield office to Boston in 2018 to help launch Prosek’s newest office (at the time!) was a pivotal moment in my career – and one I’m still enjoying! As one of the first few employees in the Boston office, I had the opportunity to help build something from the ground up while remaining connected to the broader firm. What made that experience especially meaningful was that it reflected one of the things I value most about Prosek: the ability to build a custom career. Throughout my 10 years here, I’ve been able to take on new challenges, explore different opportunities and grow alongside the firm without ever feeling like I needed to leave to find what’s next. Helping establish the Boston office gave me a front-row seat to Prosek’s growth and allowed me to contribute to shaping the culture of a new market while staying connected to the values that drew me to the firm in the first place. I’m so proud of what we’ve built and are continuing to foster in Boston, and I still love visiting the Fairfield office and working at my old desk every now and then!

Kearney: 10 years can hold a lot of pivots – here’s a few:

• Echoing Kelly in moving to Boston in 2018 to help open Prosek’s newest office at the time
• Building my own custom career, now co-leading the firm’s national security and defense technology offering
• Advice from my manager to listen and learn from those I work with that do not have the same work style as me. That’s where you can really find out what skills you want (and need) in your toolbox.
• A few years ago, I was finding it difficult to get to the next level and earn the promotion I desired. I remember those passing feelings of loneliness or frustration. What became the pivot was when I turned that emotion into motivation and drive. Years later, I still look back at that time and am grateful that the best result is never given, but earned.
• Any opportunity to teach, mentor and manage. There is always something new to learn in speaking with the next generation. As many people have opened doors for me, I hope to open even more for others in the years to come. One of the most important parts of my career is ensuring those around me feel supported, confident and inspired.

What’s it like having started together not knowing each other as PAs yet remaining close friends today?

Sheila: Working your first true full-time career job with a group of peers is invaluable. The world of corporate communications is as fast-paced and intimidating as it is exciting. Having an instant network of people that you can bounce ideas off of made us all that much stronger. We also just clicked right away – it’s hard not to become fast friends when you’re working on high stakes projects alongside each other, five days a week for 10 years. I feel truly lucky to have made such strong friendships at work. We’ve since celebrated birthdays, engagements, weddings, babies and more together. I think I stopped introducing them as my “colleagues” a few years ago. They’re just friends now!

Sarah: It’s been the best. Having a built-in peer group when entering the workforce for the first time was incredibly valuable. Of course, we had managers and mentors to learn from, but there was something so helpful about having peers who were going through the same experiences in real time: people to bounce ideas off of, compare notes with, and ask the questions we may have been too embarrassed to ask anyone else.

Fast forward ten years, and I still can’t quite believe that so many of us are not only still at Prosek, but still close friends. We’ve been through relationships, weddings, babies, promotions, challenging media situations, and so much more together. Those relationships have made the experience here even more meaningful and have truly made logging into work every day that much more enjoyable.

Katherine: As Sheila and Sarah said, it’s simply the best. Having this peer network throughout my entire career has been so incredibly helpful to my personal growth and success. While we may not work on the same accounts or even in the same industries or offices, we have all experienced the same struggles and challenges at various stages and it’s been invaluable being able to bounce ideas or frustrations off each other. 10 years later I feel so lucky that we are all still here and as close as we are. I love cheering this group on both personally and professionally and I can’t wait to see where the next 10 years takes us.

What’s one piece of advice you’d give someone joining Prosek today?

Kelly: Be resourceful and never stop asking questions. As Jen’s mantra goes, “Just Ask!”

Early in my career, I assumed that learning happened primarily in formal training sessions. While those are valuable, some of the most important lessons come from paying attention to the people around you. Even today, I learn a tremendous amount by listening to Managing Directors and Partners navigate sensitive situations, deliver difficult news or counsel clients through complex challenges. There is so much knowledge sitting around you every day if you’re willing to observe, ask questions and stay curious. Take advantage of that. The people at Prosek are the firm’s greatest resources and everyone has an interesting story or two to tell.

Kearney: Build meaningful relationships with as many people as you can. The beauty of working at an agency is that there is so much to learn from those you work with. Whether it’s leaders at the firm, our various clients, relevant media, or colleagues at all levels, the best thing you can do is intentionally get to know those around you. The relationships you nurture are what make for a purposeful career.

Related, what’s a piece of advice you wish you’d received 10 years ago?

Sheila: Don’t assume that things are done a certain way because it’s the only way or the best way. Change is good and necessary. If you can think of a better way of doing something, go ahead and suggest it. Chances are the rest of your team will be receptive to it and may even celebrate your initiative.

Sarah: A common industry expression is, “It’s PR, not the ER.” Maybe I heard that advice 10 years ago, but it took me a while to truly internalize it.

We work with clients in critical industries who expect a high level of performance, and we always strive to deliver that. Early in my career, though, I put a lot of pressure on myself and sometimes treated every challenge as if it were an emergency. Over time, I’ve learned that taking a step back, keeping things in perspective, and remembering that this isn’t brain surgery, actually helps me think more clearly and do my best work.

The work we do is important, but maintaining that perspective has made me a better professional, and probably a less stressed one, too.

Kearney: There is a difference between what you can learn from reading, versus what you will learn from experience. Time is invaluable when it comes to learning how to handle different situations and challenges. In PR, no two days are the same and over time, those experiences build fundamental skills, including the instincts, emotions, and thought processes needed to navigate each scenario. Google is your best friend, but sometimes there is no substitute for time in the saddle.

How has the industry changed over the last 10 years? Where are we headed in the next 10?

Kelly: The tools and technologies we use and have access to have changed dramatically over the past decade, but the constant has been the “relations” in public relations. While we may not be using Yahoo! Messenger to instant message each other or landlines to call up reporters, strong relationships remain at the center of what we do. This applies not only to our relationships with journalists and clients, but also to the way we collaborate with one another.

The best ideas still come from conversations, brainstorming sessions and teams working together to solve problems. Looking ahead, I think we’ll continue to see a greater emphasis on authentic, human-led communication. As AI-generated content becomes more common, trust will become even more valuable. The ability to build relationships, exercise judgment and communicate and advise with credibility will remain critical skills, no matter how much technology evolves.

Katherine: I agree with everything Kelly has said, but something else that I think has changed over the last 10 years is how we work with clients and reporters. We’ve really entered into a 24-hour news cycle where breaking news could happen at any second and we all just roll with it. Especially as we got comfortable with working from home in a post-COVID world, reporters and clients alike expect answers and updates as needed, and not always during work hours!

And while AI is not going anywhere, I think in the next 10 years, we’re going to see a swing back towards the basics. AI is so helpful in content generation, and can create so many efficiencies, but as Kelly noted, it’s never going to replace critical thinking skills, and I think we’re going to see a focus on that over the next few years.