Canadian Women in Cybersecurity 2022 | Tales from Building One of the Guardians of the Internet

Sa.

Well, welcome, everyone. Thank you to our last panel for that great presentation. And I have the honor today of sharing and having a conversation. This is supposed to be a fireside chat with the founder of Cloudflare, one of the founders, Michelle. Hi, Michelle, can you hear me?

Hi. Hi, Shelly.

Hi, everyone.

Really excited to be here. I wish I could be there in person.

Yes. Well, for those in the audience who don't know, Michelle, Michelle is a Canadian founder success story. So I, you know, when I was asked to do this conversation with Michelle, I thought I would do a lot of research. And so I was reading the research and I'm like, so how does a gal from St. Albert, Saskatchewan, end up being the first founder of Cloudflare? And that's kind of the journey I want to take with Michelle, because at a very young age, I understand you were born and raised in Saskatchewan and more of a rural community. It wasn't Regina or Saskatoon, where most of us have go for business meetings. And so tell us a bit about that journey from, you know, your hometown to when you went away to McGill. I understand. And then you won a scholarship to tell us a bit about that journey and where you thought you were heading.

Well, in many ways, Shelly, I'm kind of the great example of all the programs Canada has for people across the country. I grew up in Prince Albert, Saskatchewan. As you said, it's a small city, but went to public school and did all those extra programs that you have access to as a Canadian, whether it was forum for young Canadians in Ottawa or different sorts of things. And I. My parents really encouraged us to be committed to our communities, but also see the rest of Canada. And I fell in love with science. So I went to McGill to study science, thinking I wanted to be a doctor. But I ended up falling in love with technology and through a series of work experiences, going to get my MBA at Harvard Business School. I ended up becoming a tech entrepreneur and starting a company called Cloudflare, which is about 12 years old now. And fast forward, we're now a publicly traded company. And so it's been. It's been a journey, but one where I'm very proud of. From Saskatchewan. My parents still live there, my aunt still lives there, and I will kind of never forget where I came from.

Great. And it's great to hear about all the opportunities that we do have as Canadians. I know even at the Canadian Women in Cybersecurity event here today, there's the whis's career group that we have here, ready to talk with people there's the. The Metropolitan Toronto University. Did I get that right? Ryerson's new name, Michelle. They have a new name as of last week. TMU is a short form, but they're here as well, looking for people interested in tech and having them enter their programs. And so it's great to hear how you were able to utilize those programs. So you go to McGill, you go to Harvard. Tell us a little bit about what happened at the. The McGill Harvard transition that took you to Cloudflare. Because I think at some point when you were done at Harvard, you had to decide to take a risk and do something or go get a job.

I did. I did. So in between, I went to. Studied science at McGill. I loved living in Montreal. And then I went to Toronto and worked for many years in Toronto. And at some point I realized I wasn't going to go to medical school and that I liked working in business and I liked technology, but I was lacking some of the business foundations because I had studied chemistry in undergrad. That was what I'd studied at McGill. And so I really set my eyes to go do my mba. And this is a good story because this will happen has probably happened to some other people in the audience. And so I was applying to my MBA programs and I was applying to Rotman in Toronto, like all of the usual suspects across Canada. Ivy and I was actually at a dinner party and my sister, I have two sisters. My older one was living in Boston at the time, and I was at a dinner party at her house and somebody I did not know very well asked me. One of her friends said his name was Greg. Greg asked me, hey, what are you up to? I said, well, I'm actually applying to my mba. And in a typical kind of gruff, direct American manner, he said, what schools are you applying to? And I said, well, I'm applying. I'm Canadian, so I'm applying to University of Toronto. And Ivy and I kind of went through. And he stopped me and he looked me straight in the eyes at this dinner party in a pretty intense way and said, why aren't you applying to Harvard? And in the back of my mind I thought, well, because I will never get into Harvard is because again, I was from Prince Albert, Saskatchewan. I just, I did not. Had not seen a lot of people aspire to do that. And again, this person I did not know very well kind of said that. And I said, I didn't say that's what I thought in my head to him. I said, well, it's competitive school to get into I'm not sure it's a good use of time to apply. It's so hard to get into. And the second thing he said to me, that again, some of these things are forever in printing your brain. He looked me straight in the eye again. He said, if you don't put your name in the hat, it will definitely not get pulled. And so, being a little eager, ambitious person, I went home that night. I researched the deadlines. I had worked all out that I could still apply. Ended up applying and I got into many schools, many schools in Canada, but actually also got into Harvard. And I was like, wow, wow, I did it. And then it was like, okay, well I have to go do this. And so that brought me down to the U.S. that was my first four way foray down into the U.S. and I showed up in Cambridge, Massachusetts, which is, you know, right next to Boston with. And my eyes, Shelley, were just. My horizons were expanded immediately. People were so smart from so many different industries and walks of life and it was so global. And I had thought I had seen a lot, but I kind of got there, realized I really hadn't seen anything. And I just spent the next two years learning a lot and meeting a lot of people. And, you know, I can talk as much as you want. And so it was really this big experience and it was different. It was my first time leaving Canada. It was just much more aggressive, much more competitive, but in a good sense, not a bad sense. But I really had to straighten my spine and try really hard, work extra hard. And it was during that experience that I was trying to figure out what to do after school. And I had had all these great experiences between undergrad and my MBA where I really wanted to go be part of a team that was part of making an impact in the world. Like, that was really important to me. I wanted to be at a growing company doing something that I was passionate about, that I cared about and be part of the team that made it happen. Like, that's, that's what I was looking for. And I, when I graduated, I actually had gotten an offer at LinkedIn, which it was early, they were on a rocket ship. The person who was trying to hire me was great. He still works there. I think that my career would have gone just in a great path if I had done that. They are still private, they are about to go public. Would have been a really great opportunity connecting all of us for working professionals around the world. But in parallel, I started to work on a business idea with one of my classmates. And that's a really fun story of how we started to work on that. And it was. I did have to come to this place where I was working on a company that ended up becoming Cloudflare. We had won the business plan competition at Harvard, but it's a student business plan competition. You can only take that so seriously. And I had to decide, do I go and pursue this idea where related to cybersecurity and global performance reliability, which we'll talk more about, or should I go join LinkedIn? And I remember going to see Dan. He was the, he was the hiring manager at LinkedIn and the cafeteria in LinkedIn and in Mountain View. And I went to meet him and I said, Dan, thank you so much for the offer. Like, when I went to hbs, this is the exact job offer I set out to get. But I started a company at the same time and I got to see where it goes. And again, he looked me straight in the eye, Shelly. He said, you're making the biggest mistake of your life. And it's not that he didn't think my idea wasn't good, he just was like, this is a rocket ship. Get on the rocket ship. You've all been hiring managers probably said something similar to others. And again, it was a rocket ship. But I just had to see where my idea was going to go. And anyway, long story short, Matthew and I moved our stuff to California and I am dialing in from San Francisco, California, where I currently reside.

Yeah, that's a tremendous story. I mean, a couple of things, you know, you shared that, you know, you have, you know, why would I apply for Harvard? I'm not going to get into Harvard. Right. And somebody says, well, yes, you are. You still probably didn't really believe them. But then he, you know, he made a point of saying, well, if you don't apply, you're certainly not going to get in. So you're right then. Right. So that kind of made you keep going. And then the competition that you won, that's when you had that choice. Do I take this company idea that I have or, or do I take this great position at LinkedIn and it was a risk for you, which I believe you're probably not adverse to now that you've grown a company. But yeah. And I think as we have others in the room that are thinking about their careers and is it fair to say that your idea around Cloudflare was more passionate for you than a career at LinkedIn would have been when you were making the decision? When you look at the two choices what was the kicker that said, no, I gotta do this?

You know, I think that I get asked that a lot because there's many of you that might be thinking about starting a company or maybe you have just started or might want to in the future. And I think entrepreneurship is amazing and a great path, but it's so easy to talk yourself out of doing it. I mean, one of the ways that I see it and I again, cause I just, now that I'm in it, I talk to a lot of entrepreneurs or people who want to. Opportunities come up all the time. For every single person, every single person here, opportunities present themselves. But it's easy, or it's easy for your parents, or it's easy for your friends or your life partner or your siblings to tell you all the reasons not to do it financially. It's too risky. It's not a good time. Oh, what if it doesn't work out? These are stories we tell each other all the time. And I just see that. And so I was lucky. I was at. I didn't have a good job. I had a good job offer, but I wasn't making any money. When you're a student, you know, you're spending a lot of money, you're not making any money. So it wasn't that I had to give up a salary. I wasn't making anything. I was already kind of used to living with pretty modest budgets because I wasn't making any money while I was doing my mba. So in many ways, when I look back, I think it was kind of almost an easier decision if someone was to leave their job. Because I just was doing, I was a student, it was almost like a cover. And I was like, okay, now is a better time because it is hard to leave a well employed job. And so giving up, just choosing not to pursue one to see where this went was, I think, an easier decision for me than somebody who is really well employed at a company being like, am I going to leave my career to go start something? I think that's a really hard decision for some folks. And so for us, one of the things that helped make this an easier decision and everyone's different. I know lots of people who say, I'm going to start a company, they do whatever they can to do that. I was not that person. It was not. It's not what I set out to do. I kind of accidentally started a company, but what I liked was we had gotten into a venture capitalist. Their name was Highland Capital. They're well known, they're part of the whole Silicon Valley. They had a place in Boston and they had an entrepreneurship and residence program that we had gotten accepted into. And back to my, like, Saskatchewan roots, where I was like, well, even if Cloudflare doesn't work out, I can say that I had done the EIR program at Highland Capital. Like, it was almost like, sure, I didn't. I wouldn't have gone to LinkedIn, but I had something, a cover to put on. And which is why I think programs like Y Combinator or techstars or a lot of the programs like CDL in Toronto, like, a lot of. Or in Canada. Excuse me. A lot of these programs are great for entrepreneurship because it gives you community. And it says, I participated in this while you're working on your idea. So. So whether it works or not, you have something to put on your resume, which I think is. Which was nice. And so for me, that helped make the decision. And I will just also say that I was super lucky. I was dating somebody at the time, my boyfriend, who is now my husband. He lived in Vancouver, and he was very supportive. He's like, you should see where this goes. My parents were super supportive. My sisters were supportive. So while lots of people have people in their life saying, don't do it, I had a lot of people saying, you should see where this goes, which also made it helpful. So it was these combinations. And when I just zoomed out, all I kept coming back to is, Cloudflare's mission is to help build a better Internet, and we want to make the Internet faster, safer, and more reliable for everyone. And I kept coming back to, if we do that, I would be proud to be part of it. Like, I would be really proud to say that I was going to be part of that. And if we do this, this will be a monster company, a big company. And that was. It was all those things wrapped up that gave me. Let me lean in to try and make it happen. Now, don't get me wrong, when Dan said to me, you're making the biggest mistake of your life, I thought twice, 500 times, I was like, oh, my God, maybe I am. But I still have to see where this goes. So that was my story. So it's kind of like I fell more in love with it. And that might resonate with some of you. Others will be very definitive. I'm going to do this or I'm not. And I think that I hope what you learn from my personal journey is there's not just one way, there's lots of way to build Your careers. There's lots of ways to be successful in life. There's. There's lots of ways to start your company and have an entrepreneurial journey, and one is not better than the other. There's just lots of different ways.

Great. And so I'm assuming you still talk to Dan.

We do. I do, yes. Yes.

Bet you have great conversation now. So let's talk a little bit about your journey from building a company from ground up to where it is today to what your leadership style is. Did you have to adjust your leadership style at any point? How did you get from A to B? How did you build a company that looked at diversity, inclusivity, and women? So if you could share some of that, that would be great.

That's great. Those are all big questions, Shelley, and really important ones. So let me just give. Let me just. Because some people in the audience might have not heard of Cloudflare and other of you might know us or might be customers of us, of ours. So thank you so much. So today Cloudflare is. We're about 2,700 people around the world. We have over 4 million customers that use our service. And Cloudflare's service is to help make anything connected to the Internet, whether it's a website or application, an API, fast. We protect them from cybersecurity attacks, cyber attacks, and we help make them more reliable. About 20% of the web touches our service, our network. We run a globally distributed network, and so we work at huge scale. Yesterday, we stopped 85 billion with a B cyber attacks on behalf of our customers. So it's this, this huge network that acts like an immune system for the Internet. It's really good identifying all of us legitimate users, like Shelley or myself or any of you trying to do things. We make that experience faster and more reliable. But if you're an attacker trying to do something online, we make it a lot harder. We increase the friction and we use technology, our technology, to do that. And so it's. So it's super cool. And companies like Shopify use us. Other Canadian companies like wealthsimple, I love all my Canadian seven shifts out of Saskatoon, my Saskatchewan roots. Like, they're all Cloudflare customers as well as, like, Glossier or 23andMe. I mean, we have all sorts. L', Oreal, all sorts of companies, small to large, need to be fast, safe and reliable. So that's what we do. Today, we're 2700 people when we started. We're now publicly traded on the New York Stock Exchange. So last year we did over 600 million in revenue. Over 60, 650 million in revenue. We've been growing our revenue at 50%. And so it's this rocket ships. We sell our services to businesses, we're growing our team, we're winning customers and it's global. We have an office in Toronto in Canada as well as 16 other countries around the world, from Japan to France to the UK because all of the businesses around the world need to be fast, safe and reliable. So that's what we do. And, and it's been really great. And your question about how has my leadership style changed? Well, it's changed a lot. You can imagine when you start the company, there's three of us that started, Matthew Lee and I and we had the first two hires were two engineers. You can imagine when there was five of us sitting in a room together, there was a lot of doing, like literally doing because you got to build everything. But then when you have 200 people, you're still doing, but it's more about making sure everyone else can do their jobs. And now fast forward to today with 2700 people, but a lot of the organization reports up into me. All of the go to market teams, all of our people organization and it's now it's your. You're helping your leaders inspire their team. So it's really evolved. And I get. And I've loved every part of the, I've learned to love, I've learned to love each part of the journey. And I think that's been one of the biggest lessons where I used to get really stressed when something wasn't going right or really weighed down when someone was broken. And what I've learned along the way is in every company something is always broken. And so that's an opportunity for improvement. And so seeing it as an opportunity versus as a failure has really made my journey more healthy and I've enjoyed leadership more because of that. And you kind of say, okay, well this is a learning opportunity. And literally just this week, yesterday I had to make some hard phone calls where there were some hard phone calls. And instead of, I was thinking to myself, five years ago I would have really been weighed down from those. I would have been stressed. It would have kept me up at night. And now it's okay, this is a great learning opportunity. I'm excited to go see this. What can I learn from this? How did it go? How did I do after the fact? And I didn't lose one minute of sleep. And so I think that that's an example of how my leadership style has changed and what I do has changed. And again, I think that when I look at people who go through these paths, it's when you stop learning or growing, you get into real trouble where you feel like you're having this resistance. And often with women, not to overgeneralize. But I just, I see it a lot in my own company. And when I meet with women is, it's easy to say, well, I'm not good enough. I shouldn't be in this role. Someone is more suited to do it. And you know, it's basically imposter syndrome all over the place. And I have that too. And you kind of just realize at some point that everyone is just making it up as they go along. And so really, you're my. See, what I see as my secret weapon is how fast can I learn? It doesn't matter. Maybe you have a slow start. Maybe the first time you give feedback, it doesn't go very well. But do you get better the second, third, fourth, fifth, sixth time? And by the sixth time, everyone's now mimicking how you do it versus how they do it. And I think that that rate of what you learn can be this huge superpower when you're in a position where you're constantly growing and expanding your horizons. And so I think that's the other thing I want to out point, to punch up because I just see that all the time. And I kind of was waiting for a long time as a woman leader for someone to tell me this. I really wish someone had. I wish there had been a Greg in a room looking me in the eye, being like, you are enough, Michelle. Like, that didn't happen. And so it was kind of a realization I had to come to myself and not ask for permission, like not go get sign off. And I think that, you know, part of being a good student doing all these programs, I was always used to getting a lot of good grades and teachers giving feedback. When you become the leader, you're not getting that. So you have to kind of be in charge of your own and figuring this out for yourself, you're like, well, I run my calendar and this and then I'm going to do a great job. And so that's just been a personal shift. And again, I think I'm in a place where I'm really enjoying it. The last thing I'll just say about diversity, because this is a women in cybersecurity event, which I love, and I really wish I was all there, meeting all of you in person is, I mean we, it's so great that we have so many women in one room together. It's so great that we have so many women in the industry. And we need more because there's way more men than women. And so I best part of my job are the people I get to work with. About 30% of our team at Cloudfloor are women. Our security team is 40% women and underrepresented minorities. We're really proud of that. But we need more. And I think that all the stories you read about online are true. There's way more men than women, but there are so many great women. And so I care a lot about building diverse teams. I care a lot about helping advocate, represent being a diversity in the industry because more diverse teams run, build better businesses and are a better place to work. And so it's super important. And so I think that's something that we spend a lot of time thinking about. But it's a journey. It is not, you know, it's, you know, on this point and this might resonate with the folks. Some things that I started to see internally at Cloudflare a few years ago where we started to talk about more about this at our executive leadership level, where we would talk about, okay, how are we doing from a diversity standpoint. The first time that brought up it was like very awkward in the room. People didn't want to have the conversation. They were worried about saying the wrong thing. And what was interesting is now we talk about it a lot and everyone's gotten better at it because it's like, no, no, this is important. How are we doing? Where are we trying to get to? We're going to measure it. We're, we talk about it. We say we expect hiring managers to take this seriously. We want to make a conservative effort. We give visibility and dashboards into the hiring manager so they can see how they're doing compared to the company and their personal goals. And I think that we've come a long way. And our head of people, Janet, who I one thing she really said, she was at Twitter before Cloudflare spent her whole career in high growth companies. She has this saying, which I really, really use all the time, is when it comes to diversity, you have to allow an organization to put their foot in their mouth sometimes because by not saying something, it's worse. Like it's almost like it's better for them to have the footfall and then be like, hey, whoa, that's not cool. That did not sit well and be a place where you can quickly learn and iterate, and I think that we've really tried to employ that at Cloudflare. Now, if someone's doing something systematically wrong, that's a whole different thing. But I think that this is something that's important, so it's a topic I really care a lot about and, and think it's super important.

Wow, it's so great to see all your energy and to hear, like, you know, learning to love to do things, because we don't all love what we do, but sometimes you just have to learn to love it. How fast can I learn? You know, that could have been an obstacle for you, and you just turned it around to say, well, how fast can I learn? Putting your foot in your mouth, having the conversations, all great things that we're all trying to. To learn today. So in today's world, if you took yourself when you started out, let's say, where you're at Harvard, and you're making that decision, what do you think has changed for the young person looking today to kind of say, I want to be like Michelle. What do you think has changed for them?

Now is the time. Now is the time. So just on the entrepreneurship point, specifically, and tac. Okay, so let me zoom out. The Internet has become so important to businesses, and technology has become so important. It's not going back to how it was. It's only going to accelerate. And so if you love technology or the Internet, like, lean in, because that is a huge part of the future, and we need great people building companies and solving problems and writing policy, public policy, around it. There's a lot of work to do on the public policy side because it's just changing things. And here, let me just set the context quickly. About 10 years ago, when I started Cloudflare, there were eight tech companies that had market caps of over $100 billion. So it's companies like Microsoft and Google and Amazon and Apple and Facebook and a couple others. Okay, eight in a decade that grew to over 30. And so the $100 billion market cap is huge. That's a big market cap. That's really big. So in 10 years, we went from eight to over 30. So the acceleration, the pace, the ability to build large companies quickly in a pretty short period of time has really sped up. When we started Cloudflare, Eileen Lee wrote a really important piece of research called the Unicorns. I don't know, that's where the term unicorn came from. And she said a company that's worth More than $1 billion in valuation is called A unicorn. And at the time she put out her paper was about 2012 when she had sized it all was about four company, four to eight companies a year that were unicorns. We were one of them. So it totally tracked like Dropbox was our year. And Stripe, like we're kind of. There's like the, all the companies. A lot of Shopify, a lot of these big companies today were kind of in our vintage of starting. So you think they're overnight successes, but they really take 10 years. Coinbase, another one. So there was kind of four to eight that started every year last year alone. And the last year was very frothy. There was 386 just in 2021. And so that is the pace of innovation and technology and the Internet of what's happening. And so I think there's this huge groundswell that no one has quite put like that. We don't even really grok as a society yet, but it's happening. And so that's huge opportunity. It's huge opportunity for people here who want to start things, who want to go join a new company and be part of a growth company to help build all of these products or be part of it to make it happen. I mean, there's just a lot of new innovation that's going on. And some of them will go to business. That's how entrepreneurship works. Some will go to business, but a lot of those will become the iconic companies 10 years from now, which is super exciting and what I think is good from a trend perspective. Back to your question. So there's just something happening. I think there's lots of opportunity. My advice to people when they ask me about the career is go somewhere where it's growing. Because growth is where you learn. You're put into situations where you should be making decisions that maybe you're not quite qualified to do. And that's how you learn. Like it's, it's. You want. Growth helps solve that. If you're at a company that's kind of stagnant, I would go to one that's growing because that's probably a bigger part of the future. So I think growth is an important piece early in your career, but one trend that's different, so it's this acceleration is that it's not all just happening in the Silicon Valley anymore. Before you had to do what I did, you had to pack yourself in a U Haul. Not you didn't have to. I mean, obviously Harley and Toby didn't, but. But a lot of people packed their stuff in a U Haul and showed up in Silicon Valley. And that's kind of what the dream entrepreneurial dreams are made of. And I am part of that. Like, we did that back in 2010 when we started Cloudflare, Silicon Valley was really the only place we really seriously considered. Today, that's changed. I think a lot of companies are getting built in Toronto, in Ottawa, in Montreal, across Canada. But not just Canada, across the United States, and then many countries in Europe and in India, many countries. And I think it's because entrepreneurship is here to stay. These innovation trends are here to stay. And it's not about one city winning. It's rising all countries and many cities around the world and creating these economies and jobs and better productivity and ways of living. And that's. That's much more spread out. And I think that's good. I think that's good for Canada. I think that's good for people who don't have to leave home to go do these things. And so that is something that I see that it's very different.

Wow. Well, Michelle, our time has come to an end. This has been a great chat. I could chat longer. I'm sure everybody in the audience agrees with me. You are an inspiration. We truly appreciate you spending your time. Congratulations with your success and for sharing your time and success with all of us here today. Thank you for your time.

Thank you so much for having me, everyone. Thanks, Shelley.