“A Great Strategy Develops like a Conversation”
Drawn to a career that would expose her to unique people and challenging ideas, Chelsea Gilroy found herself hooked on the advertising world. After spending time at the likes of AKQA, 72andSunny, Giant Spoon and David&Goliath, she joined creative agency HAYMAKER where she found that creative and strategy are truly combined.
In this interview with LBB, Chelsea shares her obsession with strategy, exploring outside of her “lane” and why the best teammates go all-in on winning ideas.
LBB> Tell us about your influences growing up and how you ended up in the creative industry.
Chelsea> I never planned to work in advertising. I was not aware of all the ad schools, the major agencies, nor the legends that are so often quoted. I was torn between aspiring to produce films and what I expected was a more achievable dream of working abroad for the State Department overseas.
I chose American university hoping it would lead to working abroad for the government or a non-profit. I spent over 12 months of my four years out of the country. An internship in Dublin, Ireland at Bono and Ali Hewson’s Edun (Sustainable Runway Fashion Company), a semester at SKEMA in Nice, France, an internship in London at a social media start up, an NGO trip to Nairobi, Kenya and a class trip to Santiago, Chile to explore their key industries.
After these experiences across several countries and an internship on Capitol Hill in DC, I was excited to pursue a career that would continue to expose me to unique people and ideas that challenge my point of view. My senior year I met a recruiter from AKQA who convinced me to check it out. I’ve always been pretty technically inclined and fairly media savvy, so I was intrigued.
Shortly thereafter, I started an internship in a hybrid role of brand/strategy/production and I’ve been hooked ever since.
LBB> HAYMAKER believes in the power of creative plus strategy combined. What’s your stance on this?
Chelsea> I’ve learned over time that while many claim to combine creative and strategy, few agencies truly operate that way. What’s great about HAYMAKER is that we don’t start with the assumption of a linear process or hand off from one department to another. Ideas develop organically. There’s no single “right” way.
We may not get it right every time, but everyone is engaged during the process and ready to jump in when they can help. We are also able to recognise when to let others take the lead, without any ego. Which, more often, leads to ideas that truly resonate with consumers.
At the end of the day, I’m a firm believer that ideas can start from anywhere and the best teammates are the ones who will put their all into the winning idea – even if it wasn’t theirs.
LBB> Who/what has inspired you the most along your career journey?
Chelsea> I’ve been incredibly fortunate in my career and the most impactful experiences so far were with AKQA, 72andSunny and Giant Spoon.
At AKQA, Rem Reynolds, Liz Taylor, Mattie Yaco, Jim Beadoin, Mike Hickman, Pasha Irshad, Alyssa Waldheim (that’s just a few) had such a profound impact on defining what a great leader looks like and provided me with such a strong foundation that still informs everything I do today.
At 72andSunny, I had the chance to learn from Matt Jarvis, Glenn Cole, Max Kislevitz, Galen Graham, James Stephens, Kristine Soto, Beau Unruh, Allbriton Robbins, Robyn Pocrnich, Marc Pardy, and I know I missing many more. I began as a brand coordinator on the Truth initiative where I first met Matt Johnson and became a bit obsessed with the strategy department. I pushed to join Strategy Breakfasts (weekly casual forum of the strategy team), I persistently requested to help on projects. I was so inspired by having access to a large group of people who were like-minded and yet so different in personality and background. We discussed everything from pop culture to politics at such a nerdy level. I’m so grateful for the chance to make my switch to strategy there.
At Giant Spoon, Marc Simons, Jon Haber, Natalie Con, JM Hermann, and so many others, demonstrated what it means to think without limits and make the impossible possible. It was truly a privilege to be a part of that special place.
LBB> You have worked within the strategy space for many years. What have been some of the top lessons you have learned along the way?
Chelsea> Measure success by the impact on the consumer. It can be tempting to chase individual metrics, industry headlines or awards but it’s amazing how much you can accomplish when you focus on the consumer vs blindly following the data or worrying about who is getting credit.
There’s no one correct way but some ways are better than others. For me, a great strategy develops like a conversation. If other people in the room aren’t chiming in or building on what you have, there’s probably a better answer out there.
When choosing roles/organisations, follow your gut, not the highest salary. At the beginning of my career, I agonised over each change in position. Is it the right choice? What will I do if it’s not? The only time I had regrets was when the salary tipped the scales. All of my successes and my favourite experiences came from taking a risk and not worrying about if it “made sense”.
LBB> What do you love most about being strategy director at HAYMAKER?
Chelsea> I love that I can be more than just a strategy director. I’ve had opportunities to co-produce indie films. In another life I would enjoy being a dedicated producer. Some agencies would view that as losing focus or that I should “stay in my lane”. What I appreciate about HAYMAKER is that they not only value it, but encourage me to continue developing all of my skills.
LBB> What have been some of your highlights at the company so far?
Chelsea> Mentoring our younger talent and continuing to learn from them has been the most rewarding part of being at a younger, smaller agency. Every time they teach me some new slang from TikTok I feel “old at under 40” in the best way possible.
And I love helping shape the future of the agency. I’ve had a great string of agencies in my career but they have all been pretty established and in scale up mode. While it’s not always easy, being able to experience an agency at such a formative stage has been an invaluable experience for me. I’m very invested in understanding what it takes to develop an exceptional organisation. I love being on the team that is building and scaling an agency. It has been such an accelerated learning experience as I continue to grow in my strategy role.
LBB> What is your vision/mission for the next few years when it comes to HAYMAKER and you as a strategist?
Chelsea> For HAYMAKER, to continue to put weight behind our agency name.
A ‘haymaker’ is a punch unleashed with the entire momentum of the boxer's twisting body. It is designed to end the fight when it lands.
I love that this is the ambition of the work at HAYMAKER, that we aspire to make work that has a real impact. It can be tough to think this way when budgets get tighter, but there’s always a way.
Personally, to continue to collaborate with brands that have a positive impact on people’s lives at a broad scale in a way that reflects my personal values.
LBB> Finally, what piece of advice would you give to someone embarking on their career journey in the creative industry now?
Chelsea> Be your own best advocate. Especially as a woman in this industry, it’s a conscious choice to avoid just pleasing people and the tendency to blend in. While I don’t feel “there” yet, being further along in my career it is easier now, to feel rewarded for taking the risk to stand out, holding firm when it makes sense and not to shy away from successes. Even with the best mentor, you won’t get where you want to be if you don’t put yourself out there.
