“5 things I wish someone told me before I became a CEO or Executive” Leeann Leahy CEO The VIA Agency

Jason Malki
SuperWarm
Published in
10 min readFeb 29, 2020

As a part of our series about strong female leaders I had the pleasure of interviewing Leeann Leahy, CEO, The VIA Agency. If you drink it, eat it, clean with it, fly on it, invest with it or watch it, it’s likely a brand Leeann has worked on. She grew up as a planner at big and small agencies in NYC working on clients like Putnam Investments and JPMorgan Chase, to name a few, before joining VIA. For the past six years here, she has helped raise the profile for a broad roster of clients including ARM & HAMMER, Perdue, L.L.Bean, Fidelity, Klondike, and Lowe’s. As creator and creative lead of VIA’s “GoDo” Series, under Leeann’s leadership, VIA has being named a Best Workplace by Inc. Magazine as well as an Ad Age Small Agency of the Year in 2019. These days, she lives in an antique shipmaster’s house with her husband, their three lovely children and their pet schnerrier.

Thank you so much for doing this with us! Can you tell us a bit about your “backstory”? What led you to this particular career path?

I started out as a Strategic Planner in NYC and was lucky enough to touch a lot of different and amazing brands across a lot of categories at many great agencies over the years. I’ve worked on brands like AT&T, JP Morgan, Coca-Cola, J&J, Snapple, the NFL…you name it.

About eight years ago, I transitioned from planning to general management and joined an agency in NYC in its formative years as the President. In that position, I got a crash course in the “business of our business” which is, strangely enough, something that planners in advertising don’t really have to deal with. I learned quickly and turned a then brand consultancy into a full-service advertising agency that worked with some of the most coveted brands in America, including Spectrum, Bud Light, and McDonald’s.

In the middle of that growth period, I was introduced to the founder of my current company, The VIA Agency. In our first meeting, we laughed for about two hours. It hit me like a ton of bricks that in NYC, I was in a position where I was having a ton of success but no fun. So, I moved to Maine to join VIA and rediscover the fun in my career and my life.

After two years at VIA, I was named CEO and it has been the best experience I could ever imagine. We are thriving as an agency, working with Fortune 100 companies like Lowe’s, L.L.Bean, ARM & HAMMER, Unilever — doing some great creative work and introducing some structural changes that challenge our industry. And yes…it is all incredibly fun!

What is it about the position of CEO or executive that most attracted you to it?

I think it’s the ability to be a conductor and to try and bring out the best in people, the idea of putting them together in teams that are inspiring and unbeatable. I really love coaching; I love creating unique combinations of skills that can elevate everyone.

I’ve always had this feeling that if you’re throwing yourself into a career, you should keep growing in it and follow it through to its ultimate conclusion. If you keep growing and learning eventually you get to a top — and then hopefully to a new top!

Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

So — there’s obviously having the responsibility for running the business side of things and overseeing departments and the output, the work product and culture — those are all the things you would typically expect. The thing that I think is surprising and interesting is that, in our business at least, you have to also learn to be a gracious hostess. We’re welcoming clients all the time, including new clients. It’s a lot like being a hostess welcoming someone to your home; you’re making sure they have a great time and seeing all the wonderful things you have to show them — only in this scenario it’s the people and the work.

What is the one thing that you enjoy most about being an executive?

Solving hard problems. I like being able to help people when they’ve thought through problems from lots of different angles but are still stuck. I get to offer a fresh perspective that solves a tough situation. That’s gratifying — being able to stay at a level where you can actually see the forest and the trees.

I’m often able to say, “hold on — let’s find a different door or another way into this”, or to offer different or new resources. So sometimes I’m in a position to find solutions that others may not be able to see.

What are the downsides of being an executive?

Only that there are a hundred or so people whose livelihoods are on my shoulders, plus my own family!

Well — for better or worse — I’m always on and do feel responsible for everyone who works here and the founders and the legacy that the agency is creating. That’s a lot to carry when you stop to think about it. I sincerely want people to be happy at work, benefitting financially and proud of what they’re doing. Also, sometimes it can actually be lonely — you don’t really have any peers. I really value those peer groups that I’ve found through professional and trade associations.

What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?

Probably that it’s glamourous, that you fly first-class and eat in fancy places and go to great events every day of the week. Not so much! I think it’s also a myth that the CEO has all the answers, or that the CEO is always right. Just because I said it doesn’t necessarily mean it’s always going to be right! I’m still fallible and want to be challenged, not followed blindly. Sometimes I say or do something and everyone just does exactly that, when my hope is actually that people follow the intent, not just the directive. It’s taken some time to communicate that clearly.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

We know that women question themselves more and suffer from imposter syndrome more. Of course, women also deal with male CEO’s more than they get to deal with other women. Sometimes it feels a little like we speak a different language or struggle to be taken seriously (or even if we’re not — maybe there is that worry that we will be). You have to sort of get past all of that and just show the world what you’re made of and what you can do.

Can you share the most interesting story that happened to you since you began leading your company?

We once had two final pitches on the same day — around here we call it Epic Friday. It just so happened that we were in the finals of 2 pitches, and one was against the best agency in the country (at the time). We had a choice whether to spread them out or do them together and as an agency we decided to do them together. They both took place here in the building just a couple of hours apart, and we just galvanized the entire agency around them and we wound up winning both pitches! I’ve never even been in 2 finals in the same day, let alone go on to win both.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I’m not sure I’ve made it yet! There’ve been plenty of mistakes but at this stage of the game I don’t find them too funny — yet. Let me ask some other people and we can revisit this one again in a couple of years.

What is the most striking difference between your actual job and how you thought the job would be?

I’d say you go into the job thinking that the buck stops with you and that you make all the final decisions. But I think in reality, your job is not to be the final arbiter and the answer-giver, often your job is to ask more interesting questions and let others make the decisions.

Certainly, not everyone is cut out to be an executive. In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive?

People who are really good at big picture thinking, who have clear vision, who are rooted in integrity, people who are transparent communicators — they make great leaders. If you lack those things or you’re a micromanager; if you’re overly hung up on political things, or you get stressed easily when things are in the weeds, you’re not going to be as successful. Or if you’re doing it just for a power rush. That’s not going to move you in the right direction.

What advice would you give to other female leaders to help their team to thrive?

Believe. In yourself, in the opportunity, in what’s possible — just go for it. You can do hard things and you can figure it out. You’re never stuck in one set of circumstances. And never let your team buy into their own “mythology” …reset things in a positive light.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

My mother never gave a fake compliment or built people up in a phony way. It just isn’t her style. And so that made me want to really put in the earnest effort when I was growing up. When I was in 7th grade, I was in a production of Midsummer Night’s Dream and when I came offstage, I asked my Mom “How was it!?!?” and she sort of shrugged and said, “It wasn’t your best.” My father got really mad — but actually she was right! I didn’t really love the play and I hadn’t worked all that hard. I may have been fine — but it wasn’t my best. And that’s why “do work that makes you proud” is one of our agency principles that resonates most with me. Work that makes you proud is the best you can offer. And that is all anyone can ever ask. Thanks, Mom.

How have you used your success to make the world a better place?

I hope at least partly by the culture we have here, people feeling supported and able to go out and do incredible things in the world. But I also get to be involved in a lot of organizations; the board of United Way, the board of the Portland Museum of Art. I get to take part in some of the cultural discussions and design discussions that involve our city. The local soup kitchen and advocacy org Preble Street is going through strategic planning and they value my input on that. They’re doing great work for Portland and I am happy to offer what I can. I just encounter a lot of people who ask for advice that is so far beyond advertising and it’s flattering and I get to have a bigger impact that way. And then there are people who call and just ask for advice about their business, particularly entrepreneurs and startups. It’s nice to be able to help people who are in that phase as well.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

I would love the idea of some kind of working moms and stay-at-home mom’s togetherness initiative. A way that moms could all find a way to be more genuinely supportive of one another and realize that we’re all on the same team. It’s just such a crazy relationship that we have with one another sometimes! I don’t have guilt about working outside the home or not being able to be as involved with school, but I know so many women who do. I think it would be a great thing for the world if we could get something like that going. Really none of our jobs are more important or more difficult than the others, so let’s support each other’s efforts.

Can you please give us your favorite” Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Run Towards the Fire.” I can’t tell you how often this has been relevant in my career. When a problem is blowing up you have this sort of primal instinct to run for cover — but actually you have to do exactly the opposite. Run towards the fire. Be decisive, take responsibility, get beyond the blame game and move forward towards the fix. The more you R.T.T.F. and teach your people to do it, the more control you have over what happens. I think it also makes your employees more honest and forthcoming and helps them tackle issues more directly.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them

Richard Branson. I love how he lets his people pitch their ideas to him and then he often goes on to actually invest in them. And I love his creativity he brings to every category he’s been in. He just seems to be having fun in life. He’s a business hero of mine, for sure.

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Jason Malki
SuperWarm

Jason Malki is the Founder & CEO of SuperWarm AI + StrtupBoost, a 30K+ member startup ecosystem + agency that helps across fundraising, marketing, and design.