This is the first “beta” podcast for Marketing BS. I would love your feedback as I refine the interviews and the production quality. These interviews are all in two-parts. Part I covers the CMO’s career - how they got their first head of marketing role, and how they have pushed their career from there. In Part II we dive into one specific business they have overseen to talk about growth levers.
Transcript below:
Edward: My guest today is Jason Goldlist. Today's episode dives into his career. How he got his first CMO role and beyond. University of New Brunswick, McKinsey, INSEAD, A Place for Mom operations, and then Strategy, and then Head of Marketing at Wealthsimple. Today's co-founder of TechToronto or TechTo, among other things.
Jason, we know each other quite well, but I don't think I know the story of how you got your first Head of Marketing role at Wealthsimple. I know you're working for me at APFM leading strategy, you've done some work on television, but how did you get a marketing offer to run the whole thing?
Jason: Well, thanks for having me, Ed. I do owe a lot of my success as a marketer to you. You have been a manager and also a mentor to me over the course of my career. Quite a self-serving question, Ed, because the answer is going to be due to your guidance.
But it comes down also to the people that I've met along the way. You mentioned McKinsey in my biography. I did start my career there and I had the opportunity to meet a lot of incredible people that have served me well over the course of my career.
One of those happened to be the founder of a Canadian fintech startup called Wealthsimple. As I was working with you in Seattle, A Place for Mom, I wanted to make that transition back to Toronto, back to Canada where I'm from. I reached out to some contacts, including Mike, the founder of Wealthsimple, and told him I was coming back, and he was excited to share with me that he was looking for someone to lead marketing there. It just happened that the relationship that we'd had over many years at that point, it was a good fit for me to come on board and give it a go.
Edward: Were they looking at any other people or just your personal relationship was what got you the job?
Jason: At the time, they actually had an original marketer who joined the team, and that marketer didn't really have that third way about him. It was more of a traditional marketer who had come from a larger organization and didn't have that scrappy, thoughtful, counterintuitive thinking that the team really wanted.
They did get rid of the first marketer and were looking for someone else. They had started a search and in fact, if I remember correctly, Mike's original way of finding me was to ask me if I had any referrals for him.
He said, "Hey, we're looking for a marketer," and then he described someone that sounded a lot like me and maybe looked a lot like me and had a lot of my experience, and I said, "Oh, sounds really cool. Let me think about a couple ideas for you and then I'll bring them back to you." Then a few weeks later, we sat down and said, "Okay, I've got a couple of names for you." He goes, "Oh, yeah. I don't really want those names. I was hoping that it will be you."
Edward: Obviously, he wanted you. He knew you and he trusted you. Why put you in a marketing role and not in a strategy or an operations role where you arguably had more experience?
Jason: There's something that I've read from you, Ed, and that is marketing is everything. When the best leaders, the best founders are putting together their leadership teams, I think they recognize that.
So my background is a little eclectic. I have done work in strategy, I have done work in operations, I have done work in product, I have done work in marketing, and especially for an early-stage company that had really big ambitions, more so than usual (I think) you had to pitch in and do everything.
I think Mike recognized that was a good background for him and for what the company needed at the time and was something that I was more than eager to do, which was more than AdWords analytics, but actually anything that the company needed to grow and be successful.
Edward: It was almost less of a marketing role and more of a ‘grow the business anyway you can’ role.
Jason: Sure. I would argue that when it comes to an early stage company, in that time the company was 10 people. It had raised under $2 million Canadian in funding, had a couple of hundred consumer clients, and had its sights set on being what it is today and beyond, which is the leading fintech company in Canada with over a million Canadians as clients, managing billions and billions of dollars with the team of over 300 people.
We needed to grow. I would argue that it's actually everybody's responsibility in an organization to grow. The marketer is maybe just the one that's watching the metrics every day and making sure that all the activities that everyone's working on are adding up to the growth that we want to see of the company.
Edward: You have that job, the job you came in on for a little less than 18 months before you were promoted to GM. How did your job change post the promotion? Or did it?
Jason: It did change a lot and I think it changed more so with the growth of the company than it did with necessarily the kind of work that we’re doing in marketing or in general management. I think what's really neat about joining a fast-growing company is that there are so many opportunities everywhere to contribute and to get impact.
Something that I learned working with you is that it's much more fun to have 800% growth than just to have a 0.8% growth. Even though there are many opportunities where maybe working at one of the world's largest companies, 0.8% growth can represent a lot more dollar value than 800% growth.
But in terms of a fast-growing startup, when there's that kind of growth and that kind of excitement, there's a lot of opportunity for impact. The kind of things that I would work on started at (I would say) traditional early stage startup channels, like how do we get earned media? How do we find our communities online that want to be early adopters of our technology? How do we go participate at local events and win customers one by one?
That ended up turning really quickly into what new products do we need to introduce to keep our growth, sustain, and accelerate it? What are our customers telling us that we need to build and fix? As an example, what are the other skills we need to add to the team to grow and deliver the brand on the product promise that we've delivered with our brand?
Edward: I want to go back a little bit. I want to talk about the path that got you to the place where you got that offer. I have a theory that the things people do when they're in junior high school ended up affecting them their whole lives. Let's go back to that time when you were in junior high. What were you passionate about back then?
Jason: It's funny you mention it. When I think about my junior high experience, I was not super studious. I was not booksmart in junior high. I was the kid who was hustling his classmates in the hallways to buy from his latest venture.
I remember one of the things that I built in junior high was, you'd call it today a direct-to-consumer clothing brand. Then, I just called it ugly wear and I sold very ugly sweatshirts to my friends at school. I had a paper order form that they would use to customize. I found in the Yellow Pages, a tailor that would come and actually stitch custom logos onto the blanks that I would buy in Chinatown. I think the total cost of one of my items was like $50, which was a fortune for a junior high sweatshirt, and I probably sold it at $51 or something.
Edward: Why did you do that? Did you need that dollar that you're making? I can't imagine that was the motivation. What was the motivation?
Jason: I thought it was cool and I think that's driven a lot of the things that I've done in my career is that I find it interesting and I want to learn more about how it's done. At the time, I think the core insight to me was everyone's wearing the same clothes, everyone's looking the same. There's got to be a way to express your personality more. Why can't we order custom clothing? That just turned into a bit of a self-directed research project to figure out how it could be done. Then once it was done, how to let others do it as well.
Edward: What broader elements did you learn? You learned obviously how to make a sweatshirt. Did you learn anything that was more broad than that?
Jason: I think that's one of the earliest examples that I can remember of something I kind of live my life by now, which is GTD. How do you get things done? And how do you ship product? How do you make decisions? And how do you not necessarily delegate and outsource things, but just go and do it yourself?
I think that was a really important learning that I had from doing that. It wasn't like there was a turnkey provider who did it. It was every step of the way thinking through the process, finding out how these things get done in the real world, and then going out, getting driven around by your mom to go and do it.
Edward: You outsource nothing except for the driving of the car?
Jason: You know what? I wish we had more lax driver regulations here in Canada. I could have done it myself then. Maybe I would have Uber’d if that was around back then.
Edward: Jumping ahead to your university experience. Who’s unusual? Tell me a little bit about where you went to college and how that happened.
Jason: Part of it is because it was cool, I think applies here, too. A part of that is also sort of thinking against the grain. For me, a lot of my classmates in high school were all going to the same colleges and studying the same things. I had been successful or interested in things that ran against the grain a little bit.
I wanted to do something different and I found that at a small college in the Maritimes in Eastern Canada called the University of Brunswick, where they had a 20-person program that focused on interdisciplinary studies.
It was a philosophy degree that helped you think about the world and instead of putting you in a large auditorium and giving you a multiple choice test, they sat 20 people around a piano in an old Victorian home and had discussions with the different deans of the faculties. You were sort of ranked and rated based on learning outcomes. There were no numbers involved or attached. It was really about the impact of your thinking, the quality of your discourse, how you interacted and pushed the thinking forward together with your classmates.
Edward: How did you come out different from that experience than when you went in?
Jason: They talked about different types of programs. One that accepts great people, there's no transformation, and they come out the same. Of course, you have the stamp of approval from the program. You've got all other programs that bring in certain people and then transform them into something different.
I do think that this one was a transformational program. For me coming into it, I think I lacked perspective on how powerful those skills would be. I think I've still thought that perhaps you needed a high score in math to be successful or you needed to study engineering to know how the world works.
I think what happened is when I came out of that program, I learned really the way that we interact with each other, the way that we solve problems together, and it's not just about what you know, but how to learn and how to know is more important.
Edward: Do you think that your career and the kind of the rest of your life would have been different if you'd taken a different route if you'd gone to the University of Toronto? How would things have been different for the rest of your career?
Jason: I think it would have been really different, actually. The reason is that I think that in any other program, if I hadn't gone against the crowd, I think I would have fallen in with the crowd. I think I would have thought the same way. I think I would have studied the same things. I think I would have coveted the same graduate roles as everybody else. By striking a little bit of an alternative path for the time, it let me think in a different way and question myself, just because other people are doing it, do I need to as well?
I'll give you a great example. A very common path for people from my high school was to go in, do a college degree, go straight to a law program and practice law. Very common path for my friends, one that most of my peer group did, and those are higher-earning jobs.
Those are people who have comfortable lifestyles and are able to provide for their families very well. For me, that wasn't interesting, and I think if I hadn't made that choice, I think I would have fallen into that path. For me, instead, coming out of that program, I was really interested in the world. Part of the program included sort of a domestic internship anywhere in Canada and an international internship anywhere in the world.
Through my program, I was exposed to all sorts of different things. Having gone to the West Coast for an internship, a marketing internship, and then gone actually overseas, going to Switzerland and spending a summer there. I was curious about the world in a way that was different and I wanted an opportunity not to go to law school after I graduated, but to learn more about how the world worked.
Edward: And yet, your first job after college was at McKinsey, which many people would argue is the epitome of the traditional path for high-performing young people.
Jason: It's funny looking back at it now. It certainly looks the case and I have to agree with you. At the time, I had no idea what McKinsey was and I have to say, my family, my friends, my peer group, my school, for God's sake, do not know what McKinsey is. I did not go to a feeder school where there was on campus recruiting. I had never even heard of it.
In fact, the way that I discovered it is also quite interesting. I was doing an internship in Ottawa after I graduated and I just struck up a random conversation with someone in the community and had mentioned to them that I did that internship in Switzerland. He said, "You know what? You remind me of my nephew who's actually working in Switzerland right now for a company called McKinsey. You guys should connect."
In fact, I made that email to Rob Charon, who was in fact, finishing his second year as a business analyst in the Toronto office of McKinsey. He encouraged me to learn more about it and apply, helped me with the interview process, and helped me find that job.
Edward: If you'd gone to University of Toronto, do you think you would have ended up McKinsey anyway, maybe even without doing the internship in between?
Jason: Certainly not. I think I would have been on the path. I think I would have kept the blinders on, put my head down, and ended up following the path to the world of law or something like that.
Edward: Okay, let's play another what if. Now you're at McKinsey. You don't have that lunch, and you don't find out about Rob Charron and the opportunity, and you don't go to McKinsey. What happens instead? What does your career path look like for that alternate Jason?
Jason: We can play it out a few years. That could be fun. I do think I would go to law school. I do think I would start a job at a law firm. I do think that I would practice law, try to become a partner. I think that's the game that people try to play. I think that's a six- or eight-year game, which is kind of fun. Probably sometime along the way I become disillusioned with the art or the practice of law, and maybe I would feel the fallacy of sunk costs so strongly that I would leave private practice, just go in-house at a company, and keep practicing law in-house. I think it'd be sad. I think lawyers are sad.
Edward: Do you think you end up being the in-house counsel for Wealthsimple?
Jason: Certainly not, and the reason I say that is because the fiduciary responsibility of being the in-house counsel of a disruptive finance company is not something I want to take on, and I can't imagine that my career path would have led me to be intimately familiar with the capital market legislation in Canada. I don't think I could find that interesting. Even though we've played this what-if game where I've gone against my natural curiosity, I do think that would kick in at some point along this career path and prevent me from doing something like that.
Edward: You come out of McKinsey and instead of going directly to business school, you work for the Vancouver Olympics. How many McKinsey people were you working with there?
Jason: It was none when I started, but one of the cool things about working for an organizing committee (the Olympics) is that I think I joined as employee number 900 and something. By the peak of the games, I think there were 70,000 employees, contractors, and volunteers working for the games. So you need to scale up quite quickly.
I think all that happens in the span of six or nine months. I had the opportunity to hire some great people to join my team, but on the other hand, it's not a professionally-managed business, for example, like the one that we joined later afterwards and A Place for Mom.
Edward: What did you learn when you're at the Olympics that you wouldn't have learned if you'd done a more traditional post-McKinsey role?
Jason: It's a good question because I think this goes back to part of the career arc here, which is after McKinsey, there is also a defined path that lots of people do that I also avoided at the time. It was very fashionable to go and spend a year or two at a private equity firm or a hedge fund before going to business school and coming back to the firm. For me, that also didn't sound interesting and I wanted to try something different.
One of the things that I thought I had been missing from my McKinsey experience, even though I had managed teams of clients, is that I hadn't had a direct management role at McKinsey. As an analyst, I was doing tons of maybe big data insights, creating lots of decks, and trying to come up with strategic recommendations, but I hadn't really managed the team. I thought it would be cool to add that weapon to the repertoire and manage a big team. I think at the peak I was managing a hundred paid staff and volunteers to run the operations at the Games. That was the path that I took.
I also thought it would be cool to be part of the Olympics. I mean, the Olympics don't come to your home country all the time. The timing had worked out and I thought it'd be really interesting to take a peek inside of that organization.
Edward: Now, post-McKinsey, I hired you to come to A Place for Mom. This was the job you had before your CMO role. Why did you come work for me and what else could you have done instead?
Jason: Actually, in between there. I did do my MBA in INSEAD, so that opens up a lot of job opportunities. There's a huge on-campus recruiting push. There are all sorts of post-MBA opportunities that open themselves up to you. But I think there was a transformation that I had there where before I had been guided by what I thought was cool.
I thought clothing was cool. I thought that doing the small program was cool and interesting. I thought doing the Olympics was cool. I thought seeing the world with McKinsey would be cool. There was a bit of a transformation I underwent during my MBA, which was seeing a lot of other ambitious people that also thought some of those same things were cool.
One of the defining factors for me of something being cool was that not a lot of people want it. It made me reflect a little bit more on what I wanted to do next and the reflection led me to this new insight, which is awesome people are cool. Instead of chasing industry, instead of chasing a brand, instead of chasing experience, how can I chase great people that I could work with who would care about me, who would invest in me, who would believe in me to take on more responsibility and grow?
I made a list of people who had worked with before who I thought fit the bill and I guess you were just the first person to pick up when I called you. You told me there was a great opportunity and I think I said yes before I even asked who it was, or where it was, or what we were going to do. I just was excited about the opportunity to work with someone awesome.
Edward: A lot of your career looks like jumping from success to success and sometimes fairly randomly where opportunities kind of happen and you jump at them. What were the biggest failure points in your career? Where did things not go as expected?
Jason: It's not always up into the right in the sense that if you wanted to use a traditional measure like salary. I certainly made much more at McKinsey than I made at the Olympics. That was a major step backwards, for example.
Edward: I wouldn't call it a failure, though. Where did the failures happen? Where did things happen that at the time at least you did not expect and did not want?
Jason: The human mind is probably really good at erasing a lot of those things to be consistent with your story. But there's no doubt that at each one of those points, there are things that you want specifically, like local maxima that you're optimizing for, that you don't get.
You can imagine at a firm like McKinsey, there are lots of different projects to work on. I'm certain there are projects that I wanted that I didn't get, and even worse, projects that I had that I hated, and ones where I wasn't working with great people or didn't feel like I was, and it was a slog every day to learn, to try to be productive, to try to even just be happy.
It's the same also at the organizing committee for the Olympics. This was sometimes tedious and not exciting work. I can remember a time where I tried to make it better. I tried to apply some of the insights I had from McKinsey to some of the processes at the Olympics. After spending weeks building this macro model in Excel to help all of the volunteers get their preferred time spots on a 24 hour calendar for 77 days, I was told that I couldn't use it. I was like, what? All that time and effort that I put into what I thought, improving the process, making it more efficient, making it more effective was sort of all wasted.
I had maybe some dreams or delusions of grandeur of this product that I built, sort of being rolled out across the entire organization and maybe it would be like a legacy of the organizing committee to be passed on to the next organizing committee, the next one, and there it ended with me using it by myself.
Edward: When you left Wealthsimple, you did not move on to a new marketing role. What was your plan for what to do next and where did you end up at?
Jason: It's similar to the transformation that I had at business school, which was driven by a lot of reflection and seeing sort of people around me be successful in their own career paths. I think I got the chance to do that a lot again at Wealthsimple, which is to think about the people that inspired me, the people that I looked up to, see their career paths and where they were going, and see which parts of those I wanted to take for myself and which ones I wanted to leave behind.
I certainly saw lots of people continue on the marketing path, chase another CMO role or level up to a bigger brand with more spending, maybe one with more followers on Instagram, or maybe one that gets treated better by Google or Facebook because of their annual ad budget. That wasn't an interesting challenge for me.
The people that I looked up to, they had taken marketing skills and they had created something entirely new. I think I got pulled into more of an entrepreneurship track and thinking, how can I take some of the skills that I have and apply it to something new and different, together with the people that I want to be building with.
Edward: What's next for you?
Jason: We are starting all over again. If you think about my career progression, I started at a really big firm, then I went to a smaller organization. I went to an even tinier organization, then I went to a 10-person startup. I think I finally—like Benjamin Button—gotten back down to being born and starting with just myself.
What's next for me is building a software business in a sustainable way that's going to help really change the way that people meet each other, that people learn together, and that people grow as one and I'm really excited about it.
Edward: That's great. Well, thank you, sir. We'll continue this conversation in part two, digging into Jason's experience at Wealthsimple.
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