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.
Favourite Canadian activity:
skiing in any of the BC mountain ranges.
Canadian leadership in one word:
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
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:
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!
SVP, Corporate and Business Development at HubSpot
San Francisco Bay Area
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.
Favourite Canadian destination:
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.
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
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.
Vice President, Commerce Business and Go-To-Market, Facebook
San FRANCISCO BAY Area, CA
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 firstname.lastname@example.org.