C100 Charter Membership is a by-invitation community of influential global Canadians united in their motivation to positively impact Canada and to champion the next generation of brilliant Canadian technology leaders. They have led distinguished careers as impact-driven senior leaders, outstanding entrepreneurs, and sought-after investors.

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In a year like 2020, there is a critical element of leadership that makes good leaders, great leaders; how they lead in a time of crisis.

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We are excited that this year we welcomed 10 new C100 Charter Members: Allen Lau, Anar Simpson, Andrew D’Souza, Brian Hale, Erik Blachford, Kirstine Stewart, Michael Hershfield, Michael Scissons, Mike Wessinger and Patrick Spence.

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Meet Erik Blachford, Partner at Narrative.Fund

Former Expedia and IAC CEO, Board Director, and playwright.

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Based in San Francisco, Erik serves on boards including Peloton, Zillow Group, Siteminder, TourRadar, Liftopia, Varsity Tutors, and Busbud. Previously, he has served as CEO of Expedia, Inc. and IAC Travel (including Expedia, Hotels.com, and Hotwire), Butterfield & Robinson, and Terrapass, and as Executive Chairman at Couchsurfing. As President and SVP of Marketing at Expedia, he led the team that built the Expedia brand. Non-profit boards include Cutting Ball Theater and World Wildlife Fund (U.S. National Council). As an independent film and theater producer and executive producer, he has mounted shows at the San Francisco Fringe Festival and helped finance several independent feature films.

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You have said before that, for you, “good marketing is storytelling”. What makes a brand’s story stand out among the rest? Examples?

Great consumer brands let their customers in on a secret. That’s the essence of storytelling. When Peloton says you can be your best self, and you think, “YES”, you feel like you are part of a group that understands something special, that your personal story aligns with that brand story. It’s the same when Apple says you can Think Different, or when Norway says you can be an adventure traveler, or when Zillow says that you’re ready for a new home. We all want to be seen, and we all want to feel like we’re part of something bigger than ourselves. Brands that merge our stories into their stories, those are the brands that inspire devotion.

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You are a true renaissance man, Erik. Besides your years in leadership in technology companies, and now technology investing, what other pursuits do you spend your energy on and why do you make time for each?

I write a lot, plays, fiction, and poetry. One of my life dreams was to get an MFA in Creative Writing, which I finished, at San Francisco State. I can’t wait for Covid to be in the rear view mirror, so I can start writing and directing fringe theater plays again. I don’t pretend to be on the same level as Cutting Ball Theater (where I was on the board for years), but I’ll never stop trying. I invest in indie film here and there as well, the latest being The Nomads, which is about a rugby club being formed in inner city Philadelphia, based on a true story.

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What does “Canadian leadership” mean to you?

I think being Canadian is about thinking we’re all in this together, but also being willing to pull your jersey over your head if that’s what’s required (and we all know what I mean by that).

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How would you describe the Canadian tech scene to someone unfamiliar with what is going on at home?

I can only speak to the Montreal and Toronto ecosystems, but it’s no exaggeration to say they are both on fire. The latent in both markets rivals anything we see in most US cities. My hometown, Montreal, in particular feels ready to establish itself as a world class tech center.Meet Allen Lau, Co-Founder and CEO at Wattpad

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Meet Andrew D’Souza Co-Founder and CEO at Clearbanc

A fintech entrepreneur helping founders win by democratizing fast and affordable access to capital.

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Andrew is the CEO and Co-Founder of Clearbanc, a Toronto-based fintech platform that is now the biggest e-commerce investor in the world. Co-founded by Michele Romanow, Clearbanc has already invested $1 Billion into 2,200+ e-commerce and software companies, using data science to identify high-growth funding opportunities in less than 24 hours. He is currently an advisor and investor at Wealthsimple, Properly and Tulip Retail. Prior to Clearbanc, Andrew was the President of Nymi, a wearable platform focused on identity and security and the COO of education startup, TopHat.

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You recently told Business Insider that moving back to Toronto from the Bay Area has accelerated your Career. Can you share more of why you are so excited to be back in Canada?

To say you work for a Canadian company is a point of pride. A lot of people are disenfranchised with where society is going. For example, you look at America and how divisive society is, how divided this election has been and how the country currently is as a whole. Then, you look at Canada. If you think of most talented individuals in the world, they’d rather contribute their talents to a company that is Canadian or that operates with Canadian values. One that is focused on equality and diversity of both talent and thought.

The talent pool has become global. I could go to the smartest people in Nigeria, Indonesia or Germany and say “You can join Clearbanc, or a great Canadian company today, and you can stay where you are. However, if you decide to move yourself and your family to Canada, we can help make that happen. You will meet people that look like you, embrace you, eat food like you and you will feel at home”. That value proposition is one Canadian companies can lean into.

We’re going to have to reinvent our economy to drive our GDP. One of our biggest advantages is that we are an egalitarian, welcoming society that people are excited to move to and support.

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How have ‘Canadian values’ played a part in your journey to Clearbanc?

The reason we started Clearbanc is driven by the same fundamental Canadian value that is of equal access to opportunity. What I learned in Silicon Valley is that it’s about who you know. Those are the founders who are funded and in the press, but they’re not different from people in the middle of the country or back in Waterloo or Newfoundland with the same level of talent and ambition, but not the same level of access. Clearbanc set out to provide capital, advice, networks and opportunities at scale without the restriction of who you know of where you grew up. We’re proud that Clearbanc has already funded eight times more women than the venture capital industry average. Also, a vast majority of our team are first and second generation Canadians. When looking at improving diversity on teams, a large part isn’t what someone looks like, but rather their experience. Everyone comes from a different life experience.

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Meet Michael Hershfield, Senior Vice President of Sales at WeWork

Michael is a founder, operator, investor, and global executive who has built a career scaling consumer marketplaces.

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Michael is a cross-functional executive and entrepreneur, whose expertise spans across marketing, sales and operations, and has a keen eye for knowing what it takes to grow an organization. He initially joined WeWork as the Global Head of Growth for the Medium and Large Business Segment, he has skyrocketed in less than three years to SVP of Sales. Previously, Michael served as COO at Kitchensurfing and Nucleus Intercom. He is currently a Venture Advisor for Silas Capital and angel investor for Clay.run, Brighthire.ai and Tealhq.com. Michael is a valued Board Member of Israel Policy Forum and C100.

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Looking forward, every company is adapting to new ways we work. What trends do you see staying and leaving for the workplace in 2021 and beyond?

The extreme version of our work experience today will not survive post-pandemic, but the lessons we have learned around valuing our time with family and experiencing the value of personal time, those will stay with us in a post COVID-19 world. What will remain, is the office experience. It will adjust and adapt because our realization of what matters in life will stay with us for a long time. Companies have to adapt. We have to be sensitive to the lessons we have learned about what is most important and what we most value when together with coworkers.

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In addition to being a new C100 Charter Member, you are also a new Board Director for the organization. What motivated you to contribute your time, energy and network to the C100 mission in such a big way?

I’ve been in the US for 10 years and hit my 10-year anniversary during the pandemic. More than ever, being Canadian, being proud to be Canadian and engaging with Canadians matters to me. The C100 represents the best way for a proud expat like me to engage with the country, its citizens and to be helpful in the best way.

I live in New York City. The C100 has an emerging presence here and will play a critical role in the near future. Canadians will also play a critical role in the return of this city, in technology, in the arts and in finance. Being united as a diaspora is something Canadians will play an important role in and the C100 is uniquely positioned to play a part in that.

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Meet Allen Lau, Co-founder & CEO at Wattpad

Changing the way we tell stories, Allen Lau is a serial entrepreneur, investor and champion of the Canadian startup ecosystem.

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Since its founding Wattpad in 2006, Wattpad has grown into a global, multi-platform company shaking up the entertainment industry, with over 40 million monthly users and over 150 million original story uploads.. Stories born on Wattpad have become blockbuster movies, hit television series and bestselling books. Prior to Wattpad, Allen co-founded FeedM8, a mobile advertising company that was later acquired, and co-founded Tira Wireless, helping leading brands optimize content for mobile delivery. He is an admired leader in Canada’s technology ecosystem and is an advocate for Canadian entrepreneurs. He is also a Co-Founder of early-stage venture fund, Two Small Fish Ventures.

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In December 2019, Wattpad made the announcement to open a second headquarters in Halifax, planned to be as big as the Toronto HQ. What drove this decision?

This expansion is a major milestone in a year of incredible milestones for Wattpad. We’re a global company, with teams and partners across time zones and on nearly every continent, so a second HQ will allow us to supercharge our business as we continue to grow. Halifax is a city and community that is unmatched in Canada, with a thriving tech scene, world-class talent, and a business-friendly environment. We’re thrilled to make Halifax home to our second headquarters.

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Having navigated four crises as a leader- the dot-com bubble, SARS, the 2008 financial crisis and now COVID-19- what advice do you offer for business leaders navigating their first crisis?

The pandemic is a huge disruption that causes so many systemic changes. We have to simultaneously play both offence (i.e. seize the new opportunities) and defence (i.e. conserve cash). With time, the negative impact of COVID-19 is becoming better understood. Therefore, one should focus on seizing the opportunities. There are plenty!

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Originally from Hong Kong, attended university in Canada and was recently recognized as one of the University of Toronto’s Engineering Alumni Network Award recipients. Where do you believe Canadian educational programs stand on the global stage, particularly in attracting and retaining international talent?

Canada has numerous world-class universities and colleges. I believe Canada has done an excellent job in attracting international talents. That said, we are not doing a good enough job in retaining talent. Many students leave Canada after graduation. We should provide financial and other incentives for these top talents to stay in Canada.

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Meet Michael Scissons, CEO and Founder at the Careerlist

A serial internet entrepreneur and investor.

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Michael Scissons is a Canadian internet entrepreneur based in New York where he is CEO at Careerlist, a company he founded in 2018. Careerlist is building the first modern talent platform, pairing the industry’s top recruiters with technology that transforms the job search experience for candidates. Michael’s previous company, Flashstock, where he was co-founder and chairman, grew into the global leader in Content as a Service and was acquired by Shutterstock in 2017. Previously, Michael was the Head of eCommerce at AB InBev where he led the global eCommerce businesses, launching and acquiring operations in 10+ countries. Michael also sits on the Growth Board of Directors for ZX Ventures, the venture capital group of Anheuser-Busch InBev.

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Careerlist finds itself at the intersection of technology and recruitment to revolutionize how companies find and access top talent. What was the inspiration behind Careerlist and where you see the future of recruitment?

I have always had an unusual interest in recruitment. I think it’s because my father was in the business as a PhD psychologist and a big part of growing up was spent around it. Careerlist is exciting for me as I can combine that early interest with my knowledge in building a scalable software company.

Recruitment is about people and it will always be about people. We will see technology play a great role in finding great people, seeing how they fit, sending them offers, etc., but at the end of the day I think the future of recruiting is human.

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What is the number one piece of advice you wish you knew early in your career?

Always work in a jet stream. You want the natural pressure of the industry to carry you forward and give you the space to make mistakes and learn. If you start your career in an older industry with lots of incumbents, you will have more barriers ahead for your growth and you might progress slower. If you end up working in an area that is growing rapidly, the winds will carry you forward. Find the right jet stream and find the right tribe of coworkers. Stick with them.

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Meet Anar Simpson, Board Director and Global Ambassador at Technovation

A key influencer for digital inclusion of women and girls in technology.

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Anar is the Global Ambassador for Technovation — which equips young girls with technology and entrepreneurship skills which readies them for tech careers — and has grown the program to over 100 countries. In addition, she has been instrumental in initiatives at Mozilla, the United Nations High Level Panel on Women’s Economic Empowerment, and the US State Department’s TechWomen initiative.

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Why is it important to engage in programs and develop policies that help foster a community of young women and girls in technology?

All technologies are shaped by those who develop them (this is why early social media attempts tended to advance, not hinder, misogyny). This influence is even more apparent in digital technologies as they consume so much data and propagate so quickly. It’s important for diverse viewpoints to go into the earliest stages of these products so that they have a better chance of being used positively for everyone. Women and girls are an essential part of that. This is also why our program at Technovation is designed to educate girls on the use of technology as much as on the “how” of technology. We equip the girls with skills to be tech entrepreneurs who are thoughtful about how they can change the world.

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Women have been disproportionately affected by unemployment during the past few months due to COVID-19. What initiatives do you feel could play a vital role in offsetting these numbers?

There are two areas contributing to womens’ recent unemployment: 1) The burden of care work — by some reports more than four times as many women have left the workforce than men because they have to care for their children, their parents, or their relatives; 2) The nature of their work and their seniority — more women have been let go because they generally have less seniority and tend to fill more marginal, low-authority positions and have shorter tenures.

Initiatives to address these two factors, would be to properly compensate people for care work and re-skill workers for better jobs — yet another reason to have more women in technology-centric jobs that are more recession- and “future-proof”. There are some positive signs such as Canada’s Finance Minister putting a line item for Care Work into the 2021 budget. However, this is a large structural problem and needs more dedicated initiatives from governments worldwide. This was the focus of our work on the UN Women’s Economic Empowerment report. While these recommendations will not be enough, they are a starting point. Ultimately, there needs to be a shift away from only measuring GDP.

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Meet Patrick Spence, CEO and Board Director at Sonos

Admired leader with a long career of scaling iconic consumer electronics brands.

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Patrick Spence is the Chief Executive Officer and serves on the Board of Directors for Sonos. Patrick joined Sonos as Chief Commercial Officer in 2012. He has played a central role in the development and launch of some of the company’s most successful products and expansions into new countries. Prior to joining Sonos, Patrick spent over 14 years at RIM/BlackBerry in a variety of roles, including overseeing sales channels and country marketing operations in various regions, ultimately becoming the Executive Vice President of Sales & Marketing. During Patrick’s time at RIM/Blackberry, the company grew from $50 million in revenue to more than $20 billion, and from 150 people to more than 17,000. In 2007, Patrick was named one of Canada’s Top 40 under 40.

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To say you have a breadth of global experience would be an understatement. In light of international successes, how has your opinion on Canada and Canadian leadership shifted, if at all?

Before leaving Canada I wondered if there was something that other countries were doing or had (particularly the U.S.) that made them different/ better than Canada/ Canadians in terms of starting a movement or building a business. My twenty years have led me to the conclusion that the only thing in the way of Canada/ Canadians being more successful on the global stage is Canada/ Canadians. Our society serves us well in preparing us to be the kind of entrepreneurs and leaders the world needs more of, we just have to realize it. There’s nothing in the way of Canada/ Canadians playing a bigger role on the global stage but ourselves.

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What does “Canadian leadership” mean to you?

While it’s a broad generalization, I think Canadian leadership is humble, inclusive, & sustainable. Humble because we mostly let actions speak louder than words (maybe to our detriment at times). Inclusive because we know what it’s like to be on the outside looking in living next door to the world’s superpower — as people awaken to the importance of diversity & inclusion in building a successful company, I think it’s a natural Canadian strength. Sustainable because we build things to last vs. to flip or growth at all costs.

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Meet Kirstine Stewart, Head of the Future of Media, Sport and Entertainment, World Economic Forum

A media powerhouse, Kirstine has helped lead some of the most significant shifts in media, from the CBC to Twitter North America.

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With a board of governors including CEOs and Chairs from major global media companies including Google, Facebook, Alibaba and more, Kirstine works with the media and tech industry to keep it leading edge in a disrupted marketplace. Previously, she was VP Media for Twitter North America after successfully launching and building the first Canadian Twitter office in Toronto. Before moving to Twitter, Kirstine was the Head of Canada’s national broadcaster the CBC. She is credited with reviving the public broadcaster by introducing such hit shows as Dragons’ Den, Little Mosque on the Prairie, Murdoch Mysteries expanding CBC’s reach across TV and Radio and taking the Corp through a major digital transformation marked by the 2014 Olympics and the launch of CBCMusic’s multi channel online offer. Kirstine is an outspoken advocate for and focuses on showcasing diverse talent and is the author of the bestselling leadership book published by Random House “Our Turn”.

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Having spent time in both the traditional and digital areas of entertainment, where do you see the future of media, sport and entertainment?

Especially though pandemic, we’ve seen acceleration of change for the future of media. There has never a time where we are more dependent on content. People have mostly been stuck at home, streaming Netflix, missing sports (for a period of time) and not physically getting together. As content creators look for new ways to reach audiences, this pandemic has forced people to look at things in an innovative way as it has shifted our reality. Demand is up and resources are down. Whether it is the challenge of physically getting together or securing funding (we saw many advertisers pull out of media systems), there was a surge in demand with little resources available. Media is still valued, but how we get it to them, became the challenge.

We’re seeing a lot of interesting moves. For example in Sports, how do broadcasted games engage with audiences who would typically be in the stadium, when they are no longer there? The NBA really rose to this challenge not only by providing a safe environment for their players in the middle of a pandemic, but also by using innovative technology to bring fans virtually into the stands. This is just one example of what we needed to do in order to get content in the hands of people who wanted to consume it and create it themselves. It is a challenge when we have a spike in demand, but are looking for new ways of how to fund and create the content. Yet, it is also a huge opportunity, because we already know how many people rely and depend on entertainment and information.

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You have been a vocal advocate for female leadership for seizing opportunities, as touched on in your book “Our Turn”. What reflections have had in the 5 years since releasing your book?

At the time of releasing the book, I thought I was speaking about a new kind of leadership that was overdue and that the window for embracing that kind of leadership would be short. What I was hopeful for, was that the new wave of creative success in business was a demand for a new kind of leader. However, what we have seen is that when demands shift, they don’t shift on a straight path. We see that access and diversity initiatives can roll backwards. We’ve seen this in the pandemic disproportionately affecting diverse workers. We’re seeing women leaving the workforce at higher numbers than before. The ground made in the last couple of decades, in terms of pay equity and presence in the workforce, that people worked hard to achieve, has rolled back in a matter of months. This is deeply concerning.

I thought the book would be obsolete in 5 years and the subject would be in the rear view mirror. I’ve been asked to speak more on this topic lately, as people are concerned about the state we find ourselves in. We’ve seen unrest in the US especially and attention to voices we don’t typically hear at the table. It takes leadership to make change. Coming back and placing focus on diversity and leadership of colour, of gender and of different backgrounds, is at the forefront again. There is a new awareness of how easily progress can be lost and people won’t take no for an answer.

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Meet Mike Wessinger, Founder and CEO at PointClickCare

A natural born leader, Mike has been named one of Canada’s top CEOs, while leading an organization at the forefront of healthcare technology.

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Mike Wessinger is the Founder and Chief Executive Officer of PointClickCare Technologies. A rare Canadian unicorn and Canada’s largest private software company, PointClickCare is the leader in cloud-based software technology for the long-term post-acute care (LTPAC) market. Mike introduced the first cloud-based electronic health record (EHR) platform in the LTPAC industry in 2000 by leveraging a Software-as-a-Service (SaaS) model, the industry’s standard software delivery model today. His focus on building a strong corporate culture has resulted in PointClickCare being recognized as one of Canada’s Best Places to Work and Mike himself has been recognized as one of Canada’s #2 CEO in Canada (Glassdoor), Entrepreneur of The Year (EY) and Most Admired CEO (Waterstone Human Capital).

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In a 2019 interview with The Globe and Mail, you expressed that you were happy you didn’t take PointClickCare public in 2015. More specifically, stating that “private is the new public”. How has your decision to remain private benefited the organization? Do you feel there are circumstances and industries where going public plays an advantage?

I believe remaining private allows us to continue to focus on and invest in the long term vs chasing a quarterly number. The PE firms we have been working with share our long term view and don’t get distracted if we optimize for the long term success vs short term earnings or growth. Also, they have been very flexible in providing liquidity to early shareholder and employee option holders. The bottom line is we get everything we need from a growth capital or liquidity perspective without the cost or burden of being public. For many other companies I feel like getting public may be their only option with all of the complexities of their cap table. In our case it’s very clean. Founder-controlled and one class of shares.

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What advice do you have for business leaders on developing and fostering an authentic company culture?

We take culture very seriously. In fact we see it as our key competitive advantage. Our competitors can recruit from the same schools, pursue the same customers, copy our strategy etc. We believe that our culture helps us get the very best people allowing them to do their best work. That’s a huge advantage. A few recommendations:

- Be deliberate
- Define the culture you aspire to become
- Don’t borrow someone else’s culture. Make it your own and don’t outsource it.
- Find ways to institutionalize it (I.e. culture orientation sessions, recruit and reward systems etc)

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What is the number one piece of advice you wish you knew early in your career?

Surround yourself with people that have a high Grit Quotient (GQ).

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Visit our website to learn more about all the C100 Charter Member and how you can join. Follow C100 on Twitter, LinkedIn, Facebook, Instagram, YouTube, and right here to learn more about Canadian entrepreneurship.

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Article written by Lauren Howe, C100. Please provide any feedback to lhowe@thec100.org. Last updated: Dec 8, 2020.

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