Bossing It: Jeff Dack’s Swiss Army Knife of Skills
Jeff Dack is partner and CEO of Funday, an independent branding and advertising agency that believes that there's always fun to be had. Founded in 2019 and fully remote, the agency is built of 50+ industry vets and entrepreneurs, offering clients big agency experience with boutique vibes and exceptional value. Funday's expertise spans strategy, creative, production and media, enabling the agency to work with an array of North American brands.
Prior to his post at Funday, Jeff was CEO of Wunderman Thompson Canada where he was tasked with merging three business units (JWT, Wunderman and Mirum) into a full-service CX agency featuring creative, strategy, CRM, data, and technology services, for parent WPP. Prior to that, he was CEO of Carat Canada, Dentsu’s media business, and grew it to a hair shy of the largest in the country.
More broadly, Jeff has a unique background, having progressed from an agency creative, to a strategist, CPG marketer, then agency operator.
Jeff resides in Toronto with his wife Lisa and three children Sadie, Rachel and Dylan.
LBB> What was your first experience of leadership?
Jeff> It was likely as a C.I.T. (counselor in training) at summer camp…I would have been 15, almost 16 years old, in charge of younger campers.
LBB> How did you figure out what kind of leader you wanted to be – or what kind of leader you didn’t want to be?
Jeff> Well, I can tell you I was a pretty shitty C.I.T. Don’t get me wrong, I was full of enthusiasm and camp spirit, I was just in it for myself. Fast forward about 10-12 years, and I was leading others in an agency context. I learned then and there that it’s not about me, it’s about them, the team, and the work we produce. I also learned to have the confidence and conviction in your ideas to direct people, but not let that self-belief tip into the ego of it all.
Make it about the output and the journey, the process of getting there… and treat people the way you’d want to be treated.
Simple enough framework, but that’s how I do it to this day.
LBB> What experience or moment gave you your biggest lesson in leadership?
Jeff> It was around the year 2000 and I was just getting started in advertising. I had some early success (depending on how you define success, I guess). I was fortunate enough to work at an independent shop, a start-up agency in Toronto called ZiG (which eventually became Crispin Porter Bogusky up here years later.)
Anyways, after the three founders, I was one of the first six or eight employees, fresh out of school, having done a freelance gig previously at TBWA/Chiat Day but other than that had little experience. I was a copywriter working with an art director and we were crushing it early on with campaigns that we were getting some notoriety for, winning a few awards etc.
Well, it got to my head in the worst way.
I got briefed on a project and had the audacity to basically shit on the brief and say no, we’re not going to do whatever was being asked of us. Well, my boss, one of the co-creative directors and founders of the company, sat me down and basically asked me who I thought I was to turn down anything. Immediately, my head shrunk back down to size (Beetlejuice style) and I got it. I really had lost my way… and had she not set me on the right path, I probably wouldn’t have made it to this point. She taught me to be humble, and thankful for any opportunity I get.
That lesson has stuck with me for almost 25 years and I am forever grateful to her and the fine folks that took me under their wing and showed me what it really takes to be a pro. The way she spoke to me, how direct she was, and ultimately how supportive she was, was a huge moment for me.
LBB> Did you know you always wanted to take on a leadership role? If so how did you work towards it and if not, when did you start realising that you had it in you?
Jeff> It’s an interesting question for me, because I am an advertising generalist. I’ve had a lot of gigs and a lot of experiences, but I don’t necessarily have one superpower. The reason I mention this is because had I had that one skill I was especially good at, I may have just pursued that one thing and tried to get better at it year after year.
But I’m not blessed in that way. I was a “good” writer, ACD, strategist, marketer, operator, and consider myself (based on feedback) a good leader. So, for me, leadership has been the best use of my Swiss army knife of skills and it evolved naturally over time as I matured.
LBB> When it comes to 'leadership' as a skill, how much do you think is a natural part of personality, how much can be taught and learned?
Jeff> My leadership approach is akin to coaching a baseball or basketball team in that, many strong coaches are strong because they’ve played the position. They can relate and ultimately empathise with what every player on their team is going through because they’ve gone through it themselves.
So I think a major part of leadership is innate, but the way you relate to people and motivate them comes from what you have learned (and were taught) and how you worked on your craft for years before someone vaulted you into being the coach.
LBB> Have you ever felt like you've failed whilst in charge? How did you address the issue and what did you learn from it?
Jeff> Of course I’ve failed. Every leader has at some point, and those who say otherwise are lying. I fail all the time, although I wouldn’t necessarily call it failing. I’d call it learning and improving. From my perspective you learn way more when things don’t go according to plan. Failure versus success is too binary a way to look at it.
LBB> In terms of leadership and openness, what’s your approach there? Do you think it’s important to be transparent as possible in the service of being authentic? Or is there a value in being careful and considered?
Jeff> Over the last 10 years or so, I’ve had roughly 1000 people work on teams where I was the leader. That math is based on the size of the agencies I led, the annual turnover rate etc and a good guesstimate. Point is, I’ve also left those posts – sometimes by choice, and sometimes not – and received lots of feedback in the form of texts, calls, emails etc.
One of the most common pieces of positive feedback I’ve received from those experiences is how much people appreciate my transparency. I always tell people that 95% of what I know you can know too. Yes, I have some fiduciary responsibilities, and yes money and people “stuff” is private, but beyond that, why aren’t leaders sharing more? I don’t get it. How can I motivate people if they don’t know why they’re being asked to do something? People want context. They want to understand the plan. Want to feel a part of something, and a big part of achieving that is being open and honest with your team in good times and bad and sharing the news.
To me, it’s treating team members like the adults that they are and letting them decide if they want to be in the boat with us or not based on having the real real and not hearsay.
LBB> How important is your company culture to the success of your business? And how have you managed to keep it alive with increases in remote and hybrid working patterns?
Jeff> At Funday we like to say we’re all about “Big Experience with Boutique Vibes.” Our culture, our ethos and the way we work is critical to our success. We know if a team member, or a client is “Funday” or not, pretty quickly. It’s a feeling.
Our environment is fully remote so we keep the fun times going with games, quizzes, our unofficial mascot Ramy B, and general silliness in Slack to keep the camaraderie up. We have sacred cows we live by, and we are constantly working to ensure the conditions for success are in place so the group can be at its best and have the confidence, space, and time to create the best work for our clients.
LBB> What are the most useful resources you’ve found to help you along your leadership journey?
Jeff> Not resources, but people. Four of them. My wife and three kids. Love, understanding, imparting wisdom, being vulnerable, demonstrating patience… the qualities you need to be a good partner and parent are the same as being a good leader. It’s really just about being a good person and doing right by the team.
