Who is a C100 Charter Member you ask? In short, they are some of the most exceptional senior leaders in tech who not only have demonstrated remarkable leadership and accomplishments in their respective fields but who also hail from the Great White North. That’s Canada if that wasn’t obvious.

Get to know the seven Charter Members who joined C100 in 2021 David Baga (CEO, Even), Jen Lee Koss (Founding Partner, Springbank Collective), Andrew Lindsay (SVP Corporate and Business Development, HubSpot), Jack Newton (Founder & CEO, Clio), Michele Romanow (Co-Founder & President, Clearco), Joanna Lee Shevelenko (General Partner, f7 Ventures), and Benji Shomair.

David Baga

CEO at Even
San Francisco Bay Area
LinkedIn | Twitter

Originally from:

Surry, B.C.

Favourite Canadian activity:

skiing in any of the BC mountain ranges.

Canadian leadership in one word:
‍Gracious.‍

The piece of advice that drastically shifted your perspective: when I learned the idea of mission-driven businesses. You can have a business that is a net positive on society and that also is a great business.‍

David Baga joined Even as CEO in March 2021. Even is an “on-demand pay” startup that ‘evens’ out paychecks for workers to give them financial stability and flexibility. His career spans enterprise and consumer businesses at all stages, from ideation to billion-dollar run rates all the way through to IPO. Prior to joining Even, David was COO at Lightspeed Venture Partners, which he joined in 2019 as Chief Operating Officer. Before Lightspeed, David was Chief Business Officer at Lyft where he built the strategy and division responsible for winning enterprise customers, strategic partners, and city partnerships which grew to be over a quarter of the overall Lyft business. David was Chief Revenue Officer at RocketLawyer and spent seven years at Oracle where he built sales teams that delivered record-setting results.

What do you feel is the most important element for prospective candidates to evaluate when debating on joining a particular startup? How did you come to join Even, RocketLawyer, or Lyft?

We spend so many of our waking hours at work and sometimes that can come at the expense of other important elements of our lives, especially time with the people we deeply care about. Our time at work simply has to be worth it, and the definition of being ‘worth it’ is different for us all.

For me, it’s about impact. At Rocket Lawyer, our mission was to make legal services more affordable to all Americans, especially small businesses. At Lyft, our mission was to provide people with the world’s best transportation and improve their access to opportunities. At Even, our mission is to help 25 million people get out of the red by 2025. Each of these companies has a mission that is relatable to me. I could empathize with the people in which the mission was trying to serve, whether it was my parents being small business owners and feeling somewhat shut out of the legal system, or at Lyft where I was looking for alternative transportation and opportunities. I have been in the position of living check-to-check, wondering how I was going to fill the tank, get home, then get back to work each day.

We live in an abundant place and time in this world, and I can almost guarantee that there is an interesting company working on a problem you deeply care about and the time has never been better with remote work.

Even is the fourth organization that you have joined, entering at a C-Suite level position to a rising company. When you first join an organization, what are some of the most important first steps that you take for a seamless transition?

When you’re entering a company at any sort of senior level, it’s all about listening and learning. It’s important to create enough time and space to establish trust with people. I take a lot of time to try and understand the things that matter most. Only then do I reevaluate what needs to be added, edited, or removed. For example, if that is culture, there are elements that may be strong and have served the company really well for the phrase that they were at, but how do you add value to that culture moving forward? How do you preserve what is required and what made it special while adding in ingredients that ready the team for the next stage of the journey?

One of the characteristics of the best teams is how fast they go through learnings loops. In order to do that, you begin setting expectations for what you might be considering and what the timing might look like. By making changes that are symbolically large but in actuality are micro-adjustments, you are starting to prepping the team for a larger set of changes. These small signals are like mini down payments on future changes that you’re going to make and that eases the fear, uncertainty, and doubt that teams will naturally have when there is a new leader in the building.

Jen Lee Koss

Founding Partner, Springbank Collective
Norway
LinkedIn | Twitter

Originally from: New Jersey

Favourite Canadian destination or activity: Stoney Lake (where we have a cottage) & playing in a women’s hockey league

Canadian leadership in one word:
‍Balanced

The piece of advice that drastically shifted your perspective: Be in it for the long game

Jennifer Lee Koss is an entrepreneur and investor, passionate about supporting, uplifting, and making a change in the lives of entrepreneurs and working families. A founding partner of Springbank Collective, an organization that invests in early-stage companies that are re-imagining work, building the care infrastructure, and creating solutions for working families — with a goal of a more inclusive future.

In 2012, Jen co-founded BRIKA, an innovative retail agency focused on creating innovative, curated retail experiences. Previous to BRIKA, she worked in the management consulting, investment banking and private equity. She serves as a board member of both public and private companies in North America and Europe, and in addition, is a Julliard-trained cellist, mother of 4 young children and a graduate of Harvard University, Oxford University, and Harvard Business School.

Springbank collective is focused on “early-stage investments that focus on the infrastructure that supports women and working families”. Can you share with us more about the origin story of Springbank Collective and how this particular vertical came to be the focus of Springbank’s investments?

I have known Courtney [Leimkuhler] since we were 18 years old and played together on the Harvard lacrosse team, and I’ve known Elana [Berkowitz] since our first day at HBS. In 2018, Courtney and I started talking about the fact that despite an increasing focus on gender lens investing and backing female founders, there seemed to be huge untapped white space when it came to investing in the needs of women and working families in the real economy. As she’s prone to do, Courtney of course did a giant strategy paper on the subject and found some compelling research suggesting there was literally trillions of dollars of opportunity being overlooked. We started calling it the infrastructure to close the gender gap. We realized that our infrastructure thesis was deeply rooted in viewing the gender gap not as a women’s issue per se, but as a systems problem that touched so many different areas from work, to care to home and beyond. Elana is the BEST systems thinker I know and so I reached out to her and found that she was also spending a lot of time thinking about how to use her experience in the policy and impact world to mobilize more innovation in the private sector that would benefit women.

We started testing our hypothesis and investing together in mid-2019. In May 2020 we launched an investor collective which has grown to about 100 operator / angels who invest with us via SPVs deal by deal. In total we’ve invested in 24 companies across the infrastructure themes of care, career and consumer.

We are also passionate about the ecosystem building work we are doing around gender parity — which includes, for example, building and maintaining the first and only founder network for nearly 200 young companies building solutions in the category of family technology or FamTech.

What advice do you have for founders (especially women) who are both building great companies while raising a family?

Involve your kids in the madness. I think being really open with your kids about what you are doing is the best way for them to understand the reasons for why you do what you do!

Andrew Lindsay

SVP, Corporate and Business Development at HubSpot
San Francisco Bay Area
LinkedIn

Originally from:
Toronto, ON

Favourite Canadian destination or activity: There’s nothing more exciting than a sporting event that unites the country like the Olympics or the Raptors in the playoffs. I went to Vancouver for the 2010 Olympics when Canada was facing the US in the hockey final and it was an incredible moment of national pride. Similarly, I returned to Toronto when the Raptors were facing the Warriors in the NBA finals in 2019 and it was a week to remember!

Canadian leadership in one word: Conscientious

The piece of advice that drastically shifted your perspective: “The best time to plant a tree was 20 years ago. The second best time is now.” It resonates as both a call for urgency and as an admonishment against dwelling on regrets.

Andrew Lindsay serves as HubSpot’s SVP of Corporate and Business Development and is responsible for the company’s acquisitions, investments, and strategic partnerships. He leads HubSpot Ventures, the company’s venture capital organization. Prior to joining HubSpot, Andrew was the VP of Corporate Development at Jawbone. He was previously a consultant with McKinsey & Company and an investment banker with Merrill Lynch.

Andrew is based in San Francisco, CA, chairs the city’s TechSF workforce investment group, and is a Board Member of Asana. He is the Founding Chair of the Center for Digital Business at Howard University. He graduated from Harvard Law School and Harvard Business School with a JD and an MBA and completed an undergraduate BS degree at Howard University.

Last year, you launched the $100M HubSpot Venture CRM Platform Fund, an extension of the HubSpot Ventures Fund launched in 2018. Can you share with us more about this fund and how it came to be?

It was immediately clear to me when I joined HubSpot in 2018 that venture investing is a natural extension of our mission of helping millions of businesses grow better. Helping scaling companies grow is at the very core of everything we do at HubSpot, starting with our CRM Platform. We launched the first venture fund in 2018 to do equity investments across all stages in customer-focused B2B startups that share this commitment and participate in our ecosystem. That fund was a major success and we doubled-down last year by launching this second fund to increase our size and pace of investments. We invested in sixteen exceptional companies last year that range from seed to pre-IPO and I’m immensely proud of the impact they and all the companies in our portfolio are having on our shared customers’ success.

Last year, you were appointed to the Board of Directors at Asana. What advice do you have for those who are considering joining a BoD, especially for the first time?

Joining a public company Board is a major commitment and anyone considering it should do deep diligence first. First, ensure that the company shares your view of the future and your values. You’ll inevitably disagree on some issues with the executive team and with other directors — robust and respectful debate is essential — but you’ll be most effective if you’re all excited about a shared vision for the business and the culture being developed. Second, consider what value you would bring to the Board. Will you bring a new expertise or perspective that’s otherwise absent? Third, have clarity about what you will gain from joining.

Joining the Board of a public company is a major investment of energy and time and comes with potential liability, so you should make sure you’re comfortable with the benefits in return. It can be immensely rewarding.

Jack Newton

Founder & CEO, Clio
Vancouver, B.C.
LinkedIn | Twitter

Originally from:
Toronto, ON

Favourite Canadian destination:
‍Tofino

Canadian leadership in one word: Humble‍

The piece of advice that drastically shifted your perspective:
Steven Blank’s “Four Steps to the Epiphany” and the concept of shifting from a product development perspective to a customer development perspective was truly transformational for me in the early days of Clio.

As the CEO and Co-founder of Clio and a pioneer in cloud-based legal technology, Jack Newton has spearheaded efforts to educate the legal community on the security, ethics, privacy considerations, and benefits of running a law firm from the cloud. Under his leadership, Clio is bettering the lives and businesses of lawyers while making legal services more accessible and equitable for all through cloud-based and client-centered technology. Jack is also the author of The Client-Centered Law Firm, a #1 bestseller that’s helping law firms thrive in today’s experience-driven era.

Jack is also the host of Daily Matters, a podcast dedicated to hearing from legal professionals, industry leaders, and subject matter experts about the future of law. In Daily Matters, he explores where the legal industry is headed, how legal practice is changing, and what legal professionals can do to position themselves for success.

When you become one of Canada’s tech darlings (following Clio’s $1B valuation last April), what do you turn your focus to next? How does the game change for you as a Founder & CEO?

I have always had my sights set on building a 100 year, enduring company in Clio. The recognition of being one of Canada’s leading tech companies is a rewarding and humbling acknowledgements of progress we’re making on that path, but we have such a long way to go. One of the most energizing things for me is that my job is changing and evolving every day, so even though I’ve been running Clio for 13 years, I feel like I’ve got a constantly evolving set of challenges and opportunities ahead of me.

Love that your bio says Juggling four startups: Clio, Ian, Patrick and Isla. It’s a safe guess to say that you are a family man — how do you balance personal/family life with a rapidly growing company with big ambitions?

I had my first child, Ian, the same year I founded Clio, so raising kids has felt like an inextricable part of my journey of growing Clio. I had a lot of hesitation around having kids at the same time as embarking on the very risky venture of launching a startup, and thought the energy required by both would be all-consuming, and therefore incompatible. However, my amazing wife, Tonia, asked a question that helped settle the matter, which was “if not now, when?” So we went ahead and had Ian, and not long after Patrick and then Isla, and I’ve always found that I get so much energy and renewal from them. I wouldn’t do it any other way.

Michele Romanow

Co-Founder & President, Clearco
Toronto, ON
LinkedIn | Twitter

Originally from:
Calgary, A.B.

Favourite Canadian activity:
‍skiing in Whistler

Canadian leadership in one word: underestimated‍

The piece of advice that drastically shifted your perspective:
You’re the only one who can find your superpower combination of what you’re good at, what the world needs, and what people will pay for. And finding your superpower allows you to find great opportunities where you’ll thrive.

Tech titan Michele Romanow is an engineer and a serial entrepreneur who started five companies before her 33rd birthday. A “Dragon” on CBC’s hit show Dragons’ Den, Michele is the co-founder of Clearco, which gave entrepreneurs more than $100M in funding this year.

She previously co-founded SnapSaves, which was acquired by Groupon. Michele was also the co-Founder of Buytopia.ca, which acquired ten competitors including Shop.ca and WagJag. She’s ranked in WXN’s “100 Most Powerful in Canada” and is the only Canadian on Forbes’ “Millennial on a Mission” list. Michele is a prolific angel investor and the winner of Angel Investor of the Year award. Michele is a director for Vail Resorts, Freshii, League of Innovators, Queen’s Business School and Shad Valley.

2021 was quite the year for the Clearco team, from being the first Canadian deal from Softbank’s Vision Fund to a rebrand that was a testament to the widening product offering beyond capital. With this type of traction, what are you most looking forward to in 2022?

We’re excited to meet more founders as we continue to expand across Europe and expand our reach internationally.

You have been quite vocal about encouraging entrepreneurs to just go for it — there is never the right time to start a business. That said, what do you feel is one of the biggest hurdles as to why people don’t start that business and what can they do to overcome that?

We all have a fear of failure that holds us back. But the quicker you start, the quicker you fail and that’s where your biggest learnings come from. We have to stop thinking failure and success are polar opposites. I have yet to meet an entrepreneur who has not failed. Failure is a by-product of success.

Joanna Lee Shevelenko

General Partner, f7 Ventures
San FRANCISCO BAy Area, CA
LinkedIn

Originally from:
Mississauga, ON

Favourite Canadian activity:
‍I went dogsledding last time I was home which was pretty fun! Although I have to say that favourite is really going home to my family.

Canadian leadership in one word: Honour

The piece of advice that drastically shifted your perspective: spend time on strengths (for yourself and bringing it out in others).

Joanna Lee Shevelenko is currently Founder and General Partner at f7 Ventures, a venture capital firm focused on driving outsized returns by investing in underrepresented founders.

Joanna has over 15 years of experience in the technology sector. She is an experienced Silicon Valley COO (Atrium Legal Technology Services and Premise Data) and one of the first 100 employees at Facebook. There, she built multiple teams from the ground up including user insights, site integrity and content moderation. She also started the Facebook India office and worked on the company’s first e-commerce efforts, growth strategies, and partnerships. After her time at Facebook, she became the Chief Operating Officer of Premise Data (Series C) and later of Atrium (Series B). Joanna also serves on the Board of Directors for MPharma, a health tech company based in Ghana focused on improving access to medicine.

The seven women management team at F7 has collectively grown revenue from $0 to $15B+ throughout their careers; how did this dream team come together to form F7 Ventures?

The 7 of us have had long operating careers and met when we worked together at Facebook. Each of us have either been in investing roles or had started angel investing on our own when it was clear that a) there weren’t many women on the funding side, and b) there were many lessons in our operating careers that could and should be shared with the next generation of builders. We decided that we could accelerate our impact by coming together and combining our skillset to form f7.

You have extensive experience in building teams from the ground up. What should be kept top of mind for leaders when building out a team that is often overlooked?

The thing I always keep top of mind is to be endlessly curious. There isn’t a perspective that should be overlooked or dismissed.” If you are curious enough about why someone might have that perspective you either learn something new or you better understand someone on your team. New ideas, better communication, and better products are built out of curiosity.

Benji Shomair

Vice President, Commerce Business and Go-To-Market, Facebook
San FRANCISCO BAY Area, CA
LinkedIn

Originally from:
Toronto, ON

Favourite Canadian destination or activity:
‍canoe trips in Algonquin Park

Canadian leadership in one word: Inclusive

The piece of advice that drastically shifted your perspective: “Your life will be defined no only by the opportunities you pursue but also by the opportunities you turn down to prioritize what really matters to you”

Benji Shomair leads the Go-To-Market teams for Commerce across Meta, including Facebook, Messenger, WhatsApp, and Instagram. Previously, he scaled the advertising business, leading teams globally across business operations, global partnerships, product monetization and marketing. ‍Formerly a Principal at Bain & Company, serving clients in Technology, Media and Telecom (TMT), Consumer/Retail and Private Equity

A lot of changes have happened over 11 years at Meta, especially with new products being rolled out into the market. Are there 1–2 highlights that serve as a standout memory during your tenure at the technology giant?

I’ve had the opportunity to help build 3 businesses at Meta/Facebook — first the Ads business, then the Messaging business and currently the Commerce business. As someone who loves building, my highlights have been scaling organizations that didn’t exist before and creating new products — that proved to be valuable to people and businesses. Helping manage the transition to mobile ads as Facebook’s user base shifted from desktop to mobile and initiating the Facebook Marketing Partner/Ads API programs were both early experiences I had that taught for me how much fun it is to build things (especially at a global scale).

What “Canadian qualities” do you feel have benefited you throughout your career?

I’ve spent more than half my career in the US in global roles and in most places, people will assume I’m American. Of course, I am actually a foreigner. I’ve found the ability to be both “North American” and “International” at the same time and bridge between these two worldviews to be a powerful and unique perspective. It helps me lead in a more inclusive way, consider options that other might not and build for more global audiences. It also helps that everyone likes Canadians.

Interviews & article by Lauren Howe, Marketing & Communications manager at C100. Please direct any questions to lhowe@thec100.org.

In the United States, 7.4% of tech workers are Black (compared with 14.4% in the broader private sector). And in Canada, Black representation in the industry is even lower at just 2.6%. The same 2016 study by the Brookfield Institute found that Black employees were also the lowest paid. Less than 1% of venture-backed startups are led by Black founders.

Andre Charoo, C100’s Co-Chair and Founder & Managing Partner at Maple VC, sat down with three exceptional Black Canadian tech leaders living in the United States to share their personal and professional experiences on both sides of the border and how they are helping raise participation rates for Black talent in tech.

We’re also shedding light on a few Canadian-led programs that are working to raise these numbers and create generational impact on Black entrepreneurship and representation in tech.

Andrew Lindsay

SVP, Corporate and Business Development at HubSpot

From: Toronto, ON
Now: San Francisco Bay Area, CA

Meet Andrew: Oversees HubSpot’s acquisitions, investments and strategic partnerships, where he has built HubSpot’s partnerships function into one of the SaaS industry’s most active and successful business development groups. Prior to joining HubSpot, he held posts at Jawbone, McKinsey & Co, and Merrill Lynch. Andrew also chairs the TechSF workforce investment group, a workforce initiative providing access and educational experiences to job seekers in the Bay Area. Listen to Lindsay’s story and experiences at Howard University, an elite Historically Black University (HBCU) in Washington, D.C., here.

Alma Mater: Harvard Law School, Harvard Business School, and undergrad at Howard University.

Andrew spearheaded the creation and launch of Howard University’s Center for Digital Business, created in partnership with HubSpot.

The Center for Digital Business at Howard University, an elite Historically Black University (HBCU) in Washington, D.C., aims to educate, invest in job readiness, and recruiting efforts by creating linkages between talent and businesses.

“The Center for Digital Business is this edifice that we now have on campus is dedicated to digital business opportunities for the next generation of Black leaders.” Lindsay, being a Howard Alumnus himself, shares the motivation behind this new Center and how HubSpot could play a part in creating opportunities to amplify the impact in the Black community in America.

Lindsay’s View on Canadian Exceptionalism

“In Canada, there’s still this view of the collective whole. If my brother or sister succeeds, I succeed. It actually leads to the rising of the social safety net. That is something that Canada has maintained a belief in, despite this incredible diversity of people. That’s a place where Canada should share some of its exceptionalism with the rest of the world.”

Explaining Black History Month to his Daughters

When asked how he celebrates Black History Month, Lindsay shared that he feels a little conflicted about it.

“The push is to ensure that Black History is incorporated as a part of broader history, but to have 28 days to discuss Black history alone, often leads institutions to push all Black history into one month. I have two daughters right now and I’m not teaching them Black History Month, because the inevitable next question is, ‘what is every other month?’”.

Justina Omokhua

SVP, Brand Marketing at Endeavor and Former Global Head of Content & Lifestyle at Apple

From: Toronto, ON
Now: Beverley Hills, CA

Meet Justina: Born and raised in Toronto and daughter to Nigerian immigrants, Justina Omokhua plays a vital role in driving marketing efforts across Endeavor’s portfolio that spans across sports (UFC, Euroleague), media production, and distribution, top talent agencies (WME, IMG), and more. Previously, Omokhua served as the Global Head of Content Strategy & Lifestyle Marketing at Apple and has worked for brands like Pepsi, Nokia and L’Oréal . Omokhua has also served as a delegate to the United Nations Social Impact Summit and currently serves on the advisory boards for I.D.E.A Labs and Power Strides Career & Executive Coaching. Hear how Omokhua navigated through her exciting professional journey.

Alma Mater: York University and Rutgers University

PSA for companies: reflect internally and listen to your teams

With plenty of companies who have spoken out about their commitments to support Black talent, Omokhua shares that, while this is important, organizations should spend more energy ensuring that change is actually implemented.

“I want you to take the time to reflect internally. Ask the question of the people who actually work there. How do they feel? What do they need? That is way more important than what me, as an outsider who doesn’t work at your company, sees. If the people who work there don’t see it and feel it, then it doesn’t matter.”

“I’ve never felt more Canadian, than being in the United States”

Omokhua shares how her national pride has deepened since having moved to the United States, the warm reception Canadians receive around the world and her pride for Canada’s educational system

“It’s the idea of access — Canadians have access to learn and once you have that, it can’t be taken away from you.”

How the Black Experience Shapes One’s Professional Journey

Reflecting on her professional experiences on both sides of the border, Omokhua highlights her encounters with systemic racism, from being taught at the age of 9 that she’d likely have to work harder than her peers to being the only Black Woman in the boardroom. She also discusses the particular challenge of communicating the experience of navigating a world that doesn’t like you, to someone that doesn’t look like you.

Sean Green

Founder & CEO, ARTERNAL

From: Toronto, ON

Now: Los Angeles, CA

Meet Sean: Born in Jamaica and raised in Toronto, Sean is a serial entrepreneur blending his computer science background with an entrepreneurial spirit modelled by his mother who ran a maid-service business. Sean is the Founder and CEO of ARTERNAL, a CRM designed to help art dealers and sales directors better streamline sales processes and nurture key relationships.
Hear Green’s story on growing up in Canada and his entrepreneurial journey.

Alma Mater: B.A.Sc. York University (Computer Science) and Western University (Computer Software Engineering)

Creating opportunities for Early-Stage Black Founders through the Transparent Collective and a new venture fund focused on Black-led businesses.

You may have seen this statistic before: just 1% of VC-backed founders are Black. Sean serves as a Mentor and Advisor at the Transparent Collective, a non-profit aimed at supporting
early-stage minority founders through mentorship, coaching and introductions. Sean teamed up with Transparent Collective’s Co-Founder, James Norman, to form a powerhouse team of investors focused on helping Black founders cross the chasm from
seed to Series A.

“If you look like us, our goal is to cut you a check if you map to the same DNA that we map to — hard work, determination, grit, and hustle. You have a product and you have traction. That’s where we want to play… helping black founders cross the chasm
of seed to Series A.”

Green aims to relay that same energy to fellow Canucks, too, especially to Black founders back home.

“If you’re a founder who has grown up in Toronto, Montreal, Ottawa, Waterloo, Vancouver — wherever you are, and you look like me, I’m going to give you a pipeline to the Valley.”

Maintaining the Momentum for Black Talent in Tech

When Andre asked Green about whether or not the gap is closing “between talk and action” to support the Black Community, Green stressed the importance of the near future, “I am seeing a lot of talk, but what will materialize? That’s key. If we’re
putting in our voices, let’s also put in that muscle to shift the needle.”

Initiatives to know about in Canada

C100 is proud to partner with organizations that are actively working to raise participation rates for Black Canadians in tech. Two of these organizations include Ryerson DMZ and Real Ventures.

DMZ’s Black Innovation Programs (BIP)

The Black Innovation Programs (BIP) a first-of-its-kind program in Canada providing support to startups led by Black founders. In 2019, Isaac Olowolafe Jr., Founder and General Partner at Dream
Maker Ventures, came to the DMZ with the idea to create an environment where founders could thrive and find high-caliber mentors and the right connections to industry and capital. “Until recently, there haven’t been many programs in Canada created
to help early-stage Black tech founders overcome the unique barriers they experience”, shares Abdullah Snobar, Executive Director of the DMZ.

“Creating that early access to entrepreneurial education for young Black innovators is critical and plays a huge role in developing a diverse tech ecosystem. If we can inspire Black youth to engage in entrepreneurship early on and give them the tools
needed to succeed in business, we can foster a healthy pipeline of tech and startup talent that will go on to be a part of the next biggest made-in-Canada tech ventures.

Representation matters, and we certainly still have a long way to go to achieve it in the tech ecosystem. At the DMZ, we are of the mindset that there is always more that we can do, and more that we can learn. We will continue building on the
success of the Black Innovation Programs for years to come.”

— Abdullah Snobar, Executive Director, DMZ.

To date, the DMZ’s BIP has supported 12 Black-founded companies through the Black Innovation Fellowship, 76 founders across three cohorts of the BI Bootcamp, and over 400 aspiring entrepreneurs through the BI Launchpad. To fuel its continued success,
DMZ announced a $1 million program expansion in June 2020 and $1.2 million from the Ontario Government in February 2021.

Rep Matters, supported by Real Ventures

Rep Matters is an interview series dedicated to providing space for leaders to discuss the Black experience within the Canadian startup community and serve as a catalyst to increase Black participation in tech and VC. In this series, Phil G. Joseph,
a Black Montreal-based changemaker, dives deep with Canadian leaders across the tech industry, from VC fund managers like Andre Charoo and Isaac Olowolafe Jr. to startup founders like Brent Ho-Young and Janelle Hinds. Check out Rep Matters here.

Real Ventures is an early-stage venture capital firm that backs entrepreneurs and builds the ecosystems in which they thrive. Supporting game-changing Canadian startups, Real believes that VCs should play a role in accelerating the creation of world-class
tech ecosystems by providing support beyond the companies for whom it writes cheques. Real’s portfolio includes the likes of Mejuri, RenoRun and MindBridge (all 48Hrs Alumni).

Interviews conducted by Andre Charoo, Co-Chair at the C100 and Founder at Maple VC. Editor: Lauren Howe, C100. For feedback, please contact us at lhowe@thec100.org.‍

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.

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.

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.

Meet Erik Blachford, Partner at Narrative.Fund

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

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.

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.

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.

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).

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

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

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

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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!

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.

Meet Michael Scissons, CEO and Founder at the Careerlist

A serial internet entrepreneur and investor.

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.

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.

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.

Meet Anar Simpson, Board Director and Global Ambassador at Technovation

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

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.

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.

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.

Meet Patrick Spence, CEO and Board Director at Sonos

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

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.

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.

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.

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.

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 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”.

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.

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.

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.

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).

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.

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)

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).

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.

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