Kirstine Stewart: Making Sense of Twitter

Of all the social media platforms that have become ubiquitous to modern living, Twitter has been among the most influential. 

The company’s success, however, has been a double-edged sword: utilized to spotlight wrongdoing and organize for positive change, it can also fuel echo chambers and further divide us from one another.  

In today’s episode, Eric speaks to Kirstine Stewart, the former Founding General Manager of Twitter Canada and the former VP of Media in North America, to learn more about the company’s roller coaster history, including the multiple departures of its founder and CEO Jack Dorsey, the way Twitter has shaped the media industry and the changes she would make to Twitter if she were CEO. 

ABOUT KRISTINE STEWART: Kirstine Stewart is the former Founding General Manager of Twitter Canada and the former VP of Media in North America. She has also served as the Head of English Language Programming for the Canadian Broadcasting Corporation and the Head of “Shaping the Future of Media, Entertainment and Information” and a Member of the Executive Committee at the World Economic Forum. She currently serves as the first Chief Revenue Officer of Pex, a leading company promoting digital rights technology.


Podcast Transcript

Eric Jaffe: We make decisions every day. While some of them are small, others can have a huge impact on our own lives and those around us. How often do we stop to think about how we make decisions? Welcome to Deciding Factors, a podcast from GLG. I’m your host Eric Jaffe. In each episode, I’ll talk to world class experts and leaders in government, medicine, business and beyond, who can share their firsthand experiences and explain how they make some of their biggest decisions. We’ll give you fresh insights to help you tackle the tough decisions in your professional life.

So much of how we communicate and learn these days is dictated and driven by social media. Of all the platforms, Twitter has been among the most influential in shaping our society. Launched in 2006, the app has become the megaphone of choice for a wide range of public figures from politicians to pro athletes to muckraking journalists.

It’s proven to have both benefits and drawbacks, utilized to shine a spotlight on wrongdoing and help organize for positive change, it can also fuel echo chambers and further divide us from one another. These days, Twitter is discussed just as much for the regulation and even potential removal of specific users, most notably former president Donald Trump, as the content itself.

My guest today is uniquely positioned to help us understand how Twitter works and the impact its had on global society. Kirstine Stewart is the former founding general manager of Twitter Canada, [00:01:30] as well as its VP of media in North America, after previously working for the Canadian Broadcasting Corporation. She currently serves as the first chief revenue officer of Pex, a leading company promoting digital rights technology.

Listen in as Kirstine and I discuss the company’s rollercoaster history, including the multiple departures of its founder and CEO, Jack Dorsey, the way it has shaped the media industry, and the changes she would make to Twitter if she were CEO.

Kirstine, welcome to the show.

Kirstine Stewart: Nice to meet you. Thanks for having me on.

Eric Jaffe: You left Twitter in 2016. What was it like to work inside of Twitter during Jack’s previous departure from Twitter, because I know you were there, and then I believe you were there for his return as well. Just talking about the culture, the atmosphere, the energy would be I think really interesting.

Kirstine Stewart: Sure. Just to clarify, I actually joined when Dick Costolo was CEO. I had not been there for Jack’s earlier tenure as CEO when the company first kicked off. I did join pre-IPO. Pre-IPO is obviously an exciting time at a company like Twitter. It’s fast growing. At the time, it was very much kind of neck and neck or head to head with other social media, less like Facebook. In fact, it was kind of the same size, and Twitter, a little bit, getting the advantage because it was mobile first, as opposed to Facebook, which was still very much web-based.

Being a part of Twitter at that really formative stage and being part of Dick’s leadership team, it was a very exciting time. Cut to about three or four years later, that’s when Dick was leaving, Jack was going to be coming back as leader … I think simultaneously still with also … He was co-CEOing because he was still with Square as well. It was an interesting time to have a founder come back as a CEO, but then also be responsible for two companies at the same time.

I started out as the founding GM of Twitter Canada. It was considered to be one of the emerging markets. We learned a lot of lessons from the US team. Because I have a media background, I used to be the head of the CBC and I was at a number of broadcasters like Hallmark running the international channel Twitter said why don’t you come down to the States and head up the North American media part of the business, which I did.

Eric Jaffe: What was the common mission, if you will, at the time for Twitter?

Kirstine Stewart: I think the independence of Twitter and keeping that freedom of voice, if you want to call it, that was very important to everybody who was there at Twitter. I think it was a bit of a tricky position to sit in when you have challenges like wanting to extend anonymity to certain folks who would need protection in order to feel like they had a free voice. In certain countries where there was a concern that there would be a crackdown on either dissidents or activists, I think Twitter was very proud in saying that we stand with … I think everyone remembers the Arab Spring.

The Arab Spring was a really invigorating time, because people were very excited about the role a social media platform could play to give activists the microphone. The opportunity, whether it was in Syria or a number of other countries across Arab nations, it was the uprising and giving the voice to those that didn’t otherwise have avenues to speak to the outside world, so I think when it comes to the staff, they’re very proud of it. They might take a little sometimes too much credit than we were because you get caught up in the moment of, “Wow. If we weren’t here, this wouldn’t be happening” but at the same time, there’s a challenge because anonymity also breeds trolls and breeds all other kinds of problems.

It’s always a hard space to play in but people were definitely mission-focused, but there was a financial benefit to being so as well. Major voices started to come onto the platform, whether they were from government, like leaders of state like Obama and folks like that, or whether it was sports stars, LeBron James and all those folks started rolling out onto Twitter, having huge influence. The monetization was an opportunity to build on that and in an unobtrusive way as possible so users weren’t put off by the ads. The opportunity was to try to monetize within the space.

There was a huge amount of monetization opportunities with video. Monetization was purely based on advertisers, sponsorship, riding the content. I was there at a time when they were trying to actually convince airlines, banks, telephone companies, that it was a good thing to be on Twitter. The first experiences with Twitter and that ability for a user to reach out to them directly were not always the most positive interaction that you can imagine, if your luggage was lost or your flight was late. They wanted to stay away from it. The job that we had was showing brands how you could turn those experiences into positives and actually not just mitigate an issue that was a problem at the time but you could actually convert somebody into a more loyal user or client in whatever way.

We had folks like banks and all that say, “I’m never going to start a Twitter account. I’m just going to get abuse.” To show them actually if you could engage and have a conversation with someone, even off the and actually doing an MDM, you actually converted them deeper.

Eric Jaffe: You spoke to this a little bit about the transition but what specifically led Jack Dorsey to make the decision to come back to Twitter at that time?

Kirstine Stewart: I think there was a bit of turmoil going on at Twitter. There was a lot of high expectations around the IPO, that started to be problematic. I think it was very challenging for Dick to explain and to justify in a lot of ways when Wall Street came on a quarterly basis, directly to say where is that user growth, what’s going on, and so I think he was under a lot of pressure to make something happen in a way that people didn’t understand completely what success looked like, and how he was actually turning it around and actually was growing in a meaningful way.

I think it was a relief to people … I think we were just tired of the constant attacks on Twitter, on his leadership, on his lag behind Facebook. I think people were looking for change, and so Jack coming back again was that sense of, “Hey, this is the founder. Maybe as the founder, he innately understands it in a way that he can trigger something product-wise.”

Some things did change. He changed the lengths of tweet. The product, though, was quite belabored, and still for a number of years afterwards and only just within the last year were a bunch of products released but they didn’t always take.

Eric Jaffe: Yeah. Great segue. Why do you think … Well, how and why did Jack Dorsey make the decision, this latest time, to step down?

Kirstine Stewart: Everyone has their assumptions. No one knows but the man himself. I think he’s pretty opinionated and I guess being the CEO of Twitter, you can’t really have opinions about anything, as probably Mark Zuckerberg is finding out now with the recent shift [00:09:00] in the Meta price. It’s not fun being a CEO of a social media company anymore. It used to be a lot of fun. It used to be the rock star position, people made movies about you and they might not always be that flattering but, hey, you were a super star that people followed around.

Now you’re damned if you do, damned if you didn’t in terms of politics, in terms of deplatforming, in terms of what your influence or your impact on the world was, was largely being measured and there were agencies that were starting to come down on these guys. It was no longer the fun time as it used to be.

It’s going to be interesting to see how Parag deals with some of the challenges. One of the first product moves that was made right after he came in, and obviously was underway before he was CEO, was immediately taken down because it wasn’t thought through and it was actually something that was setting up more trolling. I think as we see now, there’s another form of product that’s being tested because the nature of Twitter being first 140 characters and then 280, you get smaller landscape. They’re looking to help creators by putting entire articles, like Medium, within Twitter. Taking the idea of Medium and putting it into Twitter.

The problem with that is there’s still a no edit button in Twitter. That’s not going to work either. It’s thinking through the impact of the change you make in real life and not having people put themselves at more risk for more abuse. I think it’s going to be a challenge to get people to post without the edit button, to actually post longer things that can then be brought back against them down the road or things they might need to edit. If you can’t edit something as a journalist, I don’t think they’re going to want to post an article on Twitter regardless of the fact that it’s a nice landscape.

Eric Jaffe: What was and what is your vision for Twitter? Did it diverge from Jack Dorsey’s vision? What about others at Twitter? Did you find that there was consensus?

Kirstine Stewart: Not dissimilar to what we’re hearing about the kind of unrest that happened at Google and Facebook and now Spotify over the terms of service they want to put in for engagement content, because the Joe Rogan controversy, there’s going to be divisiveness within a company when you have different political and different value systems. That happened also at Twitter.

The cover of, especially the early days, a mix of naivete, positivity, and a little bit of ego mixed in there, was a dangerous mix for a bit. It was the mix that put them into a few situations where they didn’t think things through in terms of the impact of some of the products that they were putting out.

I think my role as someone who had come from traditional media and seeing how much media influences society and a number of us who, like me, had come from the traditional media space were trying to set off warning bells a little early about content moderation, about what does it mean to have a free voice on a platform? If that free voice feels that it’s been hounded off the platform, is there true free voice? Because they’ve been trolled off.

These platforms are all private. They could make whatever rules they wanted to from the very beginning. If they had been maybe more stringent, behaviors would not have gone as crazy as they have and maybe there would not be this need for government or policy makers to feel that we need to step in over them now to regulate. Self-regulation would have been a nice idea but it needed to be done quite early I think before it got as slippery as it does now.

Now they’ve gotten to deplatforming and you see the reactions of people. They’re now trying to put bills forward that force social media platforms to take anybody and not to deplatform them, which is in a world of Nazis and horrible other voices that are wanting to take their microphones on platforms like this, it’s a pretty dangerous place to be.

Eric Jaffe: Looking at the pro/con balance sheet of social media, and saying we can’t put the genie back in the bottle but this maybe is a net negative for society, how do you think people look at that?

Kirstine Stewart: Yeah. I think anybody on any social media platform right now is probably wondering what they could do better. I think I look at it as someone who worked in it, what was my responsibility? What could I have done differently or better? I think there were a number of people who tried to raise voices.

It’s difficult when people don’t understand what the end play is. It’s difficult when there’s a lot of folks who are focused on the product rather than the impact of that product. There is a big gap between what engineers and products can do or understand about society. They’re not necessarily taught ethics or those kinds of things in the same way that others are.

Eric Jaffe: At least within the US, there’s this perception that it’s like the elites on Twitter and it’s an echo chamber for the elites and the elites think that everything that happens on Twitter matters so much and that most Americans aren’t on Twitter. How does Twitter do you think think about that? How should they think about that?

Kirstine Stewart: It actually is quite in line with the mandate of a business. When you think about the challenges of user growth, it was always being asked internally, what can we do to make our platform more accessible, more reachable, more engaging for users? User growth was a major driver of a company’s valuation, because it was usually value times users.

We talk about echo chambers and that’s a huge challenge but it’s one that is hard to dismantle because to those people in those echo chambers, the people in the echo chamber are the ones that matter the most to them. They don’t necessarily want to bust their echo chambers either.

I think for Twitter, the push to growth, more product accessibility, or bandwidth accessibility to support the product was needed earlier to get it more ubiquitous. You’re not posting funny pictures or it’s not cat videos necessarily on Twitter. There is kind of a need to be engaging and use a voice and that demands a lot of people. It’s not a passive experience to be on Twitter. If it is, then it’s not probably a very fun experience.

Eric Jaffe: Facebook, obviously, does have greater user penetration, a broader user base. They have overcome that. Have they done something right that Twitter hasn’t done? Have they done that clumsily? What’s your take there?

Kirstine Stewart: We’ve just seen in recent days, the drop of the Meta value I think was over 25% last night. I don’t know how much … It was 23% I think at the open, first day post their latest quarter that showed user growth slipping and didn’t just grow. The user base actually slipped for the first time or maybe second time in their 10 year history.

This is a challenge for all social media platforms. It’s going to be interesting to see where it lands. I think asking big social media companies to grow much more is going to be a challenge. They’re trying to hang on at this point.

Eric Jaffe: How do you see the future of news consumption? How do you see that changing and Twitter’s role in it?

Kirstine Stewar.t: Social media is a distributor of news. It’s not a creator of news. It doesn’t hire journalists. It’s almost like as carriers of news, the social platforms got to build their businesses, literally, off the backs of the work being done by traditional media in that sense of news.

But news also needed the distribution of the social media platforms to keep relevant to whole new audiences that weren’t going to turn on their televisions, their radios or pick up newspapers anymore. It was a marriage made in strange places. One got probably better advantage of it at the end, and then things started to happen. As society starts to be able to … You’re no longer a broadcaster or a newspaper with the same relationship with your readers or followers. They’re talking back to you. Social media is a two way street.

It’s a multiple conversation and people start to point out what they think is news or news becomes less valid when you think about the influence of non-factual information on public through a pandemic, through an election. These are times when people need the real truth and there’s now a question of what is the truth? What is media? What is news?

Eric Jaffe: Without going down a whole political rabbit hole but, obviously, former president Trump’s Twitter feed, he’s probably the most prominent person ever to have been deplatformed. What impact did his Twitter presence have? What impact do you think the deplatforming of him had?

Kirstine Stewart: This is something where I can claim some bit of personal experience because I was the head of the government team for North America when Donald was … Trump was already on the platform, because he had a personal account, he was on The Apprentice, and he was a celebrity.

When it changed to a government account, because he became one of the nominees for the Republican nomination, back then, that was something that as a service, to all qualified nominees, Twitter supported them through onboarding and explaining how to use the service. We helped to onboard Donald Trump as well as anybody else who was a qualified candidate at the time.

Eric Jaffe: Wow.

Kirstine Stewart: You’re giving someone a microphone. Again, this was something that was inherent in the values of Twitter. How do you regulate that, moderate that, in a place where you’re saying, “Well, I’m not a media company, so that conversation can happen on my platform and go at it. The good shall win”, I think that’s the naivete part that I referred to earlier.

I do believe that nobody thought that they were setting up anything that would bias to negativity. I think everyone thought the good will prevail. Having been from the traditional space of media, a lot of us were saying that’s not going to happen not human nature. There’s a reason they say what bleeds, leads.

Everyone has an opinion now and everyone is an expert and when everyone is an expert, then no one is. That’s been the challenge. Deplatforming the worst of that or trying to deal with the Joe Rogans of the world, again, it’s a bit late to do it now and people only … They only view it with suspicion. If they’re fans of that, if it’s confirmation bias and you’re saying exactly what a lot of people want to hear, what is the truth anyway? It gets very murky.

Eric Jaffe: When you onboarded Donald Trump as the nominee, was that an actual in person or, I don’t know, over Zoom interaction with him personally? Did you onboard his team?

Kirstine Stewart: The candidate and their team. I think in the case of Trump, he came around the New York offices and had a tour to see … It’s what you do as the media team to get people comfortable with … There’s some folks in the same kind of roles that wouldn’t be comfortable with the microphone, so you’re trying to get them to understand what they can say, can’t say, don’t get themselves in trouble.

There’s a lot of how-to play on social media, whether it’s Twitter or Facebook, in a way that can get you the most followers, it can get you the most, “This is what you should do if this happens. Don’t ever tweet your location until after you’ve left”, safety concerns that you want to teach people in roles that are high profile, so all of that. Don’t ever put your address, this is what happens if you say somebody else’s address. There were basic rules about what would get you kicked off the platform but it just got very murky.

Eric Jaffe: Okay. Last question for you. You’re the CEO of Twitter starting tomorrow. What is one product, innovation, change, that you would want to implement if you started as CEO?

Kirstine Stewart: I think I would actually do a couple things, if I could do two things.

Eric Jaffe: Okay. Two. Deal.

Kirstine Stewart: More global offices. I think there is going to be a challenge, the more US-centric any of these social media platforms become, and Twitter very much so is very US-centric. A lot going on there in the world. You’ve got to be more global.

Then, secondly, because I’ve been talking about it enough times, an edit button. I don’t believe in just going in there and being able to change anybody’s thing or being able to go back and change their … There could be track changes, whatever, but there should be the ability … I know a number of us have tried to say something and said something completely wrong or something else that they didn’t mean to say, because they just needed an auto-correct or an ability to edit button and it hasn’t happened and it needs to happen, even if there is some kind of rules around how you use it.

That would be what I’d do, go global and give a little more control to the user.

Eric Jaffe: I like it, the micro and the macro. Well said. Well, Kirstine, such a pleasure to have you on. I feel like we could talk for another hour. Thank you for coming on the show and being so candid. I thought it was a really, really fascinating conversation.

Kirstine Stewart: No. Thank you. I appreciate the dialog. They were great questions. It’s always great to talk about this.

Eric Jaffe: That was Kirstine Stewart, the former head of Twitter Canada and VP of media for North America, among other roles. My biggest takeaway was the striking degree to which based on how Kirstine described her experience there, Twitter’s success has been a double-edged sword.

When it launched, it would have been hard for its founders to foresee how massively it would be adopted, how influential it would become, and some of the other unique challenges that massive growth would pose. It’s a cautionary tale for founders to make sure they are bringing in the right experts to advise about how best to navigate future phases of growth, to help them see around corners, and to anticipate the challenges that are coming.

We hope you’ll join us next time for a brand new episode of Deciding Factors featuring another one of GLG’s network members. Every day, GLG facilitates conversations with experts across nearly every industry and geography, helping our clients with insight that leads to true clarity. Feel free to leave us a review on Apple Podcasts. We’d love to hear from you. Or email us at if you have feedback or ideas for future show topics.

For Deciding Factors and GLG, I’m Eric Jaffe. Thanks for listening.

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