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Digital Design Leadership: Dominic Bortolussi


Dominic Bortolussi, CEO of The Working Group, is an avid believer in teamwork and collaborative leadership. In this interview, he discusses how he discovered his style of leadership and the fascinating path that led to the company’s success as a digital agency.

Hear from the other digital design leaders we interviewed


Dominic Bortolussi: So, I’m Dominic Bortolussi, I’m founder of The Working Group, we’re a web and mobile software company. We’ve been around since 2002, and we have offices here in Toronto and New York. I’m the CEO, so my customer really is my team, and making sure that everybody who works here can achieve and become the best that they are.

Richard Banfield: So, being a founder you obviously had that leadership role from the beginning. What was the moment when you realized you were actually leading a group of people, and not just running a business that maybe you went and founded?

Dominic Bortolussi: Hmm, yeah. I think I had a number of really good conversations over the past three or four years. And through those conversations I discovered what type of leader I am. And I discovered that I’m the leader meritocracy, a democratic type of leader, a leader who asks opinions of other people and expects them to step up. Not an autocratic leader, not a me-first leader, not a top-down leader. And through that exploration I discovered that really my customer is not my clients. My customer is my team. And that was a interesting shift, because I always assumed that my customer was my clients, you know, were my clients, people that I was building software for. So, that was a not so subtle shift that’s happened over the last couple of years. So, I guess my recognition of my type of leadership has evolved over those past few years.

Richard Banfield: And has it changed who you are? Did you need to change any part of your personality to do that?

Dominic Bortolussi: I think it is still happening now, so, yes. No, I didn’t need to change my personality, I needed to change my perspective on what my role was. I think until I started having those conversations, at times I was uncomfortable with my thoughts as to what leader I was. Did I need to be the talk-down person, commanding and bargaining orders out to everyone, ’cause that was a role on the position that I was uncomfortable in. And so it turned to be good that I discovered that as a different type of leader and that I need in a different way. And uh… So that brought with it much more comfort than what I thought I was gonna have to do as a leader.

Richard Banfield: So, obviously that change required you to learn a bunch of new skills. How did you acquire those skills?

Dominic Bortolussi: So, I started working– Number of ways. I started working with a coach, a life coach I suppose, a life or leadership coach. And he introduced me to a lot of interesting literature, a lot of ways about thinking about leadership. I did it through speaking with a number of peers and people that I admire in technology space here in Toronto and elsewhere. I did it by attending events with other, you know, creative agency leaders, like Owner camp, at the Owner camp. So, it was a few things; reading, speaking with people who have knowledge about that and looking within myself to try to figure out how I wanted to navigate this shift.

Richard Banfield: Great. What– As you’ve evolved from being just a founder to being a leader of the team of people, you have obviously had to deal with the stress that come along with that business. Not an easy job. Tell me a little bit about how you balanced those things out, and don’t completely lose your mind.

Dominic Bortolussi: Right. So, one thing for me and for The Working Group is, there’s a lot of leaders here. I also have three other partners, they’re full partners in the business. And they are each phenomenal leaders in their own area. You know, we have Chris Eben here, he’s very visible in the community, does a lot of speaking engagements, is very active in our business development. And so his leadership is very visible in sort of a traditional corporate leader. He was out there speaking and pointing direction. Andrés is also a phenomenal leader. He leads all of our project operations, and has amazing empathy and ability to connect with people. So, his leadership is really through example and through his amazing communication abilities. Jack is our technical leader, technical director. And he’s type of leadership is through example by doing– He’s perhaps the most dedicated worker I know who, you know, put his head down and solves problems with people. And he’s getting really good at incorporating other people into the problem-solving system. So, how have I– The question I think was initially, “How I’ve dealt with–

Richard Banfield: How did you acquire new skills, and which ones did you feel like you needed versus maybe the ones that your partners could take care of?

Dominic Bortolussi: Yeah. So, I think it was, a bit of it was delegation, in terms of leaning on my partners to be at the lead in areas that I wasn’t as good at. And part of it was discovering what I am good at, and the type of leader that I am. And through speaking with knowledgeable people, mentors and reading, I developed those skills just through practice, and by setting aside about an hour each week, generally on Fridays, you know, to do some writing and thinking about how I want to continue with that shift. So, just setting aside time.

Richard Banfield: What about to beyond the work space? How do you balance your life? I’m guessing you have a family and balance with that stuff.

Dominic Bortolussi: Right, yeah. Well the neat thing about The Working Group, and probably a lot of entrepreneurs who started their own company, is that we all have plan for The Working Group to be our product, to be the tool that allows us to maximize our own lives.
And so baked in that is the idea that we can take time off if we need to. And that the other partners are there to cover for us. That extends to everybody here at The Working Group. You know, we anticipate that people have their own journeys and their own life paths that they have to take. Sometimes that means that they need to take a month off, or two months off to go traveling. And rather than trying to, you know, hug them so tight that they never leave, we give them the comfort and flexibility to do that. And that of course starts at the top. So, by having four great partners who can cover for each other we’re able to allow the flexibility that happens. You know, I don’t have any kids, Jack and Chris have kids, Andreas doesn’t have any kids either. We’ve got… we’re in totally different stages in our life growth and we have different needs. And so having a really strong relationship between the four partners and making sure that we give each other flexibility needed builds a great partnership and the great business for us.

Richard Banfield: So, having four partners obviously has all sorts of challenges in terms of pointing the company in the right direction. How do you guys tackle the “where are we going” conversation?

Dominic Bortolussi: Yeah. So, with a lot of communication. We now shifted to a one hour morning meeting every morning where we have progression of topics that we speak on. So, Monday is about projects, Tuesday is about sales, Wednesday is about people in the team, Thursday is about legal office administrative, Friday is about vision. And, you know, by setting that side of time and by having an agenda that we continue to refine and go through, we’re starting to build that regular routine of checking in with each other.
That’s part of it. The other part is that we discovered we needed to ensure that our own personal life visions and missions were aligned with what The Working Group was. And we were fortunate enough when we did that exploration that they did in fact have to tell nice things what The Working Group is all about. So, we’ve got lucky in that sense, or maybe we knew it all along and that’s why we became partners. But I think that’s critical. If you have a business with a number of partners and the objective of one person is to become a billionaire, and the objective of another person is to spend a ton of time with their family and maintain that lifestyle of entrepreneurship, there’s gonna be a conflict. So, uncovering that early is probably a very wise thing. And then if you do find that you are well aligned, then building the tools and the process to keep communication lines open and make sure that you maintain that alignment.

Richard Banfield: Great. When it comes to putting a team together beyond just the four partners, how have you gone about doing that? And has it changed overtime with your philosophies or strategies for building that team changed?

Dominic Bortolussi: So, initially when we were small, you know, from 7 to 15 people, the focus when I was hiring was always on billable production people: developers, designers. I was doing the project management and Andreas was doing the project management. So, every single person at the company until we were about 15 or maybe up to 20 was pretty much production people. And the objective then was to find people that were aligned with how we work. You know, we enjoy our work together, we ask for excellence. Don’t we have a lot of fun doing it. So, finding people that were aligned with that, who are really good at what they did, and who wanted to build a career as a master craftsman, whether that’s a developer or designer.
Once we hit a certain point somewhere after the 20s, it became painfully evident that we needed a few more types of roles built into there, you know, more project management, more product management, or an office coordinator, an office admin. Now we have an HR person. You know, there’s a number of roles that emerged overtime. And so that’s how the team has shifted. So, now, when I’m interviewing people I’m still looking for that lifestyle and mission fit, and, you know, that cultural fit so you knew that people get along. But the skill set has broadened from being just an amazing designer or developer to having a lot of other types of skills. Project managers, now that we have dedicated project managers, it’s an interesting skill set, you know, it’s like detail oriented. And people who enjoy the communication, people who are able to manage clients, you know, manage the accounts well, so it’s a different skill set than what a developer needs to have.

Richard Banfield: Are there particular qualities you’re looking for in those folks?

Dominic Bortolussi: In anyone?

Richard Banfield: Yeah. That’ll be on maybe the hard skills. What are the general philosophical or soft skills that you’re looking for?

Dominic Bortolussi: Well… I don’t know. I don’t know if I’m gonna get in trouble by saying this but I mean I love hiring immigrants, and first generation people. Yeah. I mean, they’ve got all the passion of a building career in a new country, in a new place. Work ethic is amazing, the attitude is amazing. There’s no self-entitlement. And this is of course not to say that everyone who isn’t, you know, a first generation or an immigrant doesn’t have that, but… And I don’t go out of my way only to hire immigrants, but I find that we have a high number of people that are recently settled in Canada, or whose parents were settled in Canada.
And, yeah, I don’t know why that is, but, I mean, we all get along really well. I think maybe it’s the nature of the industry, that, you know, it’s stem focused, you know, there’s a lot of science technology piece of it, it tends to seem to favor a lot of people from, you know, Asia, South Asia, East Asia, as well as in the Middle East. So, we’ve got a very diverse team here. And we’re trying to get more gender balanced as well, which is another challenge. You know, we’re sort of becoming the classic agency where all the designers, or half of the designers, are women, and all the developers are men. And we’re trying to change that, and we’re trying to encourage that change. That’s an ongoing–

Richard Banfield: To try and get some balance?

Dominic Bortolussi: Absolutely.

Richard Banfield: So, if somebody was to ask you to describe the culture of The Working Group, how would you describe it?

Dominic Bortolussi: You know, The Working Group is suppose to be, we’re aiming to be the best studio in the world to learn and to work and to grow at. And the growth part is intentionally vague. Personal growth, career growth, skill growth. You know, everybody here loves what they do. They want to become master craftsman in what they do. And so we’re trying to create an environment that allows that to happen. That’s my objective. It’s to make an environment and put in the process, the people that will allow everyone to become the best at what they do.

Richard Banfield: If you were to do all over again, what would you change? What mistakes might you avoid, or obstacles might you, hurdle?

Dominic Bortolussi: Hmm… Um… I would… I’ve started my transition from working in the business and doing the day-to-day in the project managements, and putting my fingers in the dike.
I would’ve started the transition away from that earlier. It’s easy to say in hindsight. But, even now, you know, I’ll find myself, you know, two hours in, asking myself, “Oh, God, why am I doing this? I shouldn’t be doing this. We have people that are much better at this than I am. I need to step back slowly and get someone to help with this, so that I can go off and do other things.” So, that transition is always difficult, it’s a classic problem for entrepreneurs. But, if I could’ve become that, or if I could’ve recognized that earlier it would’ve been better.

Richard Banfield: And going forward what do you think the opportunity is for you as a leader or for your team of partners to know what skill sets may you still need to work on and what are the gaps that you still need to fill?

Dominic Bortolussi: Yeah… Yeah… I do… I don’t know. You know, I think the four partners, we need to continue to get better at, you know, choosing a direction for the company, because it does get difficult at times when you’re got four helmsman who each have, you know, a common direction they want to go but different tactics about how to get there. So, we need to work on that. And I don’t know if that means that we should bring in an advisory report, we’ve been exploring that possibility, to help us with those decisions, or to help with structuring. Yeah, that would be probably the key thing.

Richard Banfield: And then lastly, when you look at the industry as a whole, that space that we operate in as businesses, what do you see coming down the line that are opportunities and challenges and trends?

Dominic Bortolussi: Well, I think one thing that we’re uncovering for ourselves, you know, and I speak to… our own perspective on this is that as the size of our clients grows, getting bigger and bigger national and international companies, we’re realizing that in a vendor they’re looking for someone who provides more than just the production, more than just slaps out a design and development of a piece of software, whether it’s a web or mobile product, and hands it off and supports it.
They’re looking for the smarts and the strategy in advance of that. And we’ve always provided that, but we never focused on that until recently. Because our genesis was as a development shop. We were guys behind the scenes who’ve been coding the apps. And, you know, as the size of our projects has grown and the need for that type of strategy has grown and our recognition of that means that– I think agencies are gonna be able to offer more and more of that type of work in concert with the development process. And using an agile process, which is something that we’ve adopted over the last three or four years, the strategic thinking is very tightly intertwined with the production. You know, every cycle that you go through goes through a piece of strategic process, a strategic thinking about what you want to develop and why you wanna develop and how to prioritize that. So, educating our clients into that process I think is gonna lead to better things, to better production, to better software. So, I think that’s a common theme that we’ve seen with a lot of our peer agencies around here is that, rather than just being the design and dev shops, they’re being asked their thoughts and their expertise into how to design or what to design for a client based on their business needs.

Richard Banfield: Dom, thanks for your time. Really appreciate it.

Dominic Bortolussi: You’re welcome. Thanks, man.

If you’d like to learn more about Dom and his team, check out The Working Group’s website of follow Dom on his Twitter account or bug him for more info via email.

Author Richard Banfield

As CEO, Richard leads Fresh Tilled Soil’s strategic vision. He’s a mentor at TechStars and BluePrintHealth, an advisor and lecturer at the Boston Startup School, and serves on the executive committees of TEDxBoston, the AdClub’s Edge Conference, and Boston Regional Entrepreneurship Week.

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