Kirstine Stewart: On lifelong learning, and on breaking new ground at TribalScale


This interview with Kirstine Stewart, President and Chief Revenue Officer at TribalScale — an innovation firm delivering first-in-class product strategy, design, and development across platforms — was conducted and condensed by Jodi Kovitz.  Kirstine Stewart is also the author of the best-selling leadership book, Our Turn, and is an advisor to #movethedial and TheBigPush.

Q. You have had a remarkable and impressive career.  How did it start?

I started in media, my first job was a Girl Friday at a television production company. I was changing water bottles and filing papers.  From there I became a salesperson, then I was managing international sales, and then I became a President of the division by the age of 30. I believe it was a combination of luck, opportunity, and being open to new possibilities.

Q. How and why did you move into tech?

My first foray into tech was when I moved to Twitter.

I moved from the most important job at the CBC to 140 characters because I was excited about connecting users to content in a new way, and the power of data to understand and drive people’s choices. I also like to be where the action is, I am entrepreneurial that way.  I don’t want to be the one following; I want to be there at the beginning.

When I first arrived in tech, I believed that it was a new frontier for women; a new place to go and to have a voice.  Marissa Meyer had just been made CEO of Yahoo when she was 6 months pregnant.  The historical rules didn’t apply as there weren’t any; they were being made up as we went along, so it was a more open playing field for women.  Seeing other female leaders thrive got me excited.

Once I was in the tech space however, I realized that it was not exactly the opportunity that it should have been then. That’s why I am excited to be working with organizations like #movethedial: the moment is now.

Tech is the way of the future, and it is a place that everyone and anyone can reinvent.  I think there is opportunity to do so. I love what’s happening in AI and thinking about how we can connect to human beings.  I am most hopeful that the space corrects itself, and gets to a place of fertile ground for women, men, people of colour, and where everyone can come together and build a new industry.

Q. Tell us about the new role, and why you wanted to go to TribalScale.

After leading Twitter’s expansion into Canada, I moved to the US and ran all of Twitter’s North American Media Partnerships. I have always had a passion and ability for bringing partnerships and content together.

I then realized that I wanted to go back to Canada, and I moved into the role of CSO at Diply, a social entertainment publisher that creates content for millennials. I had a great experience and our team accomplished a lot. I am proud that Diply was ranked #1 as the fastest growing company in Canada by Deloitte, and I am excited to stay on as one of their advisors.

I recently realized, however, that I wanted to get deeper into the pure tech space. I became curious about machine learning, voice, AI, etc.

TribalScale is at the forefront of these new technologies, and I want to deeply understand them. After scaling from 6 to over 130 employees in two years, and expanding globally, the founders recognized that it was time to bring seasoned leadership experience to the table. I joined TribalScale because I feel I can both contribute my leadership experience and learn at the same time: it is a great marriage.

On top of that, I align strongly with the founders’ values around diversity of thought, and the skills at the leadership table, which are both very important to me at this stage of my career.

I spoke at TribalScale’s TakeOver Innovation Conference. When the conference was first announced, Sheetal (who I will be running the company with) very clearly said that he would be setting up the conference with a 50% gender-balance (which he will often say he did after being inspired by #movethedial). TribalScale ended up surpassing this target and had more female speakers than male speakers, which shows real initiative from the top.

Q. You’ve been a business leader for a long time. What is it specifically about #movethedial that resonates for you?

I get approached by a lot of groups and organizations doing great work.  They all have good intentions.  It was more important to me, however, to find a connection with an organization that had the belief, but also the skills and mechanisms to make a real movement happen.

I am very passionate about supporting you and your team’s efforts with #movethedial. We all want to see a shift and better representation in the space, but because so many groups are working on different parts, it needs someone to pull all these people together and make the movement significant. That’s what I believe in what you and #movethedial are doing.

Q. Tell me a bit about what you believe influences you from your early years.

My parents were immigrants to Canada.  They instilled a sense of having to pull up my bootstraps and work hard. At the same time, they were very supportive and always made me believe I could do whatever I wanted. Whether I was a son or a daughter, it didn’t matter, I was a person first.  They expected the best of me, and for me to do my very best.  

Q. What do you want the world to know about TribalScale?  

I think that TribalScale is in this unique position where it’s not only a unique business at the forefront of tech and innovation, but it’s also investing in its own right. TribalScale takes on new partnerships and prioritizes collaboration. What they are doing in the automotive and banking industries is fascinating. They are always thinking about helping someone else and are teaching others how to be innovative. Opening the door to innovation is what TribalScale does on the service side.

When I first told Diply I was moving into an advisory role, I started looking for opportunities on the VC side. I thought I had a lot to give and that it was a good time for me to head in that direction. But in TribalScale’s Venture Studios, they are one step further and are looking to move ahead by investing in companies early, and are moving forward on a lab-type basis. It will be be interesting to help them with services but also to support incubators and generators, nurturing and investing in business, that’s interesting to me.

Q. What gets you excited when you think about the year ahead?

I think AI and and the technology opportunities in Canada excite me most.  I know there is a lot of focus on Montreal but I am excited about the role that TribalScale will play, not only in Canada but internationally.  They already have a strong presence in Dubai and in New York City. Tech isn’t confined to borders.  I am excited about seeing how far we can take it, and to show that Canadian skills are highly valuable and needed on the international playing field.

Q. You are a tremendous role model. Can you share a few pieces of advice?

Be open and ready for anything. In Our Turn I share what I mean by this: decide that there is nothing you can’t go for and win, especially if you apply yourself and be a good person. At the same time, let go of expectations and let your passions guide you.  Careers are not all a straight line, yours can be a jungle gym, but it might be magnificent. Maybe one path will be a dead end but finding success and passion is all about being open to opportunities and keeping your head up.  

Hard work, and going above and beyond, is very important. Don’t underestimate it. Starting at the bottom in my Girl Friday role taught me that you can absorb and learn a lot when you are willing to do anything and make yourself useful.  Making yourself useful and noticed is the best thing you can do to invest in your own career. That helps people see you as being helpful and useful in the next job.

I don’t believe in balance, I believe in work/life flow. Sometimes it’s 90% work and sometimes it’s 90% home.  It’s hard as you can’t always anticipate, but you have to go with it and do the best you can.

Lead yourself, with authenticity. If the first task of leading is to figure out your goals, the first responsibility has to be to lead your­self, understand and stand up for your values, your vision, and yes, your own style. To be anything other than authentic will inevitably compromise your confidence. It will also compromise the trust others place in you. You can’t lead effectively, or for long, without earning and keeping the trust of the people you work with. Authenticity matters, and it matters more today than it ever did.  When the line between public and private has blurred, and when so many interactions take place in a virtual sphere, a leader has to walk her talk.

articleElektra Simms