Taking the Road Less Traveled: A Q&A with Executive Creative Director, Jeanie Caggiano

Nearly 40 years ago, Jeanie Caggiano received a rejection letter from Leo Burnett. “I wish I would have kept it,” laughs Jeanie.  

Being rejected didn’t stop her. Since then, Jeanie has spent her entire professional career with Leo Burnett, with over three decades of creative experience as one of the Agency’s most influential and award-winning creatives. Jeanie’s hallmark trait is taking the road less traveled: taking on the hardest categories and transforming challenges into creative solutions for her clients.  

We sat down with Jeanie to learn more about her storied career and gain insight into how future generations of creative talent can learn from her non-conformist approach to leading and learning as an advertising agency leader.  

Q: What’s one of the biggest obstacles you faced as creative lead on the Bank of America account and how did you overcome this obstacle? 

A: Well, when I was approached to be the creative lead on this account, I was undergoing cancer treatments. And I was also running UnitedHealthcare as both creative lead and business lead. So, balancing all that with my lower level of energy was a huge challenge. I couldn’t even walk up the stairs without having to sit down for five minutes to catch my breath. I was tempted to say “no,” but I said “yes,” and I’ve been glad ever since. Both the UHC and Bank teams did a fantastic job of supporting me during this time. They helped me continue doing the work I love without having to sit around all day thinking “Oh god, I’ve got cancer…”. Working helped me keep my mind busy and I was able to overcome the physical obstacles of my illness by doing the work that I love with such a supportive and encouraging team. Plus, being able to work remotely was a godsend. 

Q:  How do you characterize your approach to work? You’ve been with Leo Burnett for over 35 years spearheading some of the Agency’s most influential campaigns—are there any common themes that you can attribute to successful campaign work? 

A: I try to make people go, “I never thought of it that way before.” Taking a different point of view, making people WANT that product, telling a memorable story—those things make for successful work. Brave clients know that, and I’ve been lucky enough to work with quite a few.  

Q: You’re passionate about mentorship and helping new creatives rise “through the ranks.” What’s your favorite thing about developing team members? 

A: I’ve been a mentor through Leo Burnett’s Mentorship program, which has been a HUGE honor. I also really value giving real-time feedback to my creative teams. Feedback that feels hard to give is often the most valuable, especially when it’s fresh. I encourage each creative to get out of their comfort zone—it may be a beautiful place, but nothing grows there. I think back to my career and realize some of the hardest feedback I received was what I needed to hear most.   

Q: Do you have a mantra or a favorite quote that embodies your approach to work? 

A: I have SO many. But one of my favorites is a quote from Voltaire that says, “be regular and ordinary in your life, so that you may be violent and original in your work.” Throughout my career, I’ve taken some of the hardest clients—the ones many creatives don’t want to touch—and helped my clients turn their work into gold. I wouldn’t know what to do with a new cereal flavor, but give me something that’s a thorny challenge, and I thrive.  

Q: What have been some of the most memorable moments and successes of your career?  

A: It’s hard to pick one success—I’ve led work on P&G, Allstate, UnitedHealthcare and other clients that won 11 Cannes Lions. I was also invited to be a juror at Cannes, which was amazing. 

Maybe the most memorable was when started working on United Healthcare several years ago and sold a campaign for health insurance featuring crazy ways people got into the healthcare system. I loved it, but I was surprised they bought it—and even more to my surprise, the launch spot we created went viral and was the most watched commercial in the world for three weeks running. It also won Gold at Cannes. All of that made me laugh, because at the time, I was 56. And this is an industry that worships youth. 

 But while industry accolades are nice, I take pride in how I’ve been able to create change in boring categories (like car insurance, health insurance, and now banking). My hope is that I can inspire other creatives to be bold and courageous in their work and ask for the hard problems—that’s where creatives often have the greatest opportunity—because there isn’t as much competition.  

Q: Any final “parting” advice to creatives looking to make an impact in their work? 

A: Creative that doesn’t make you go “I want me some of that” is invisible. We get paid to show up every day and tackle the industry’s hardest challenges. We won’t always succeed. But if we continue to show up, especially when it’s hard, our creativity has the power to turn difficult problems into something moving and truly worth celebrating.