Shopify Alumni: Founders and Investors

Shopify Alumni Fueling Canadian Startup Ecosystem

Recently, significant leadership changes were announced at Shopify. Jean-Michel Lemieux, the company’s Chief Technology Officer, and Brittany Forsyth, Chief Talent Officer, have both declared their departures. Furthermore, Joe Frasca, the Chief Legal Officer, is also preparing to leave the e-commerce leader, with all three concluding their roles in the coming month. It appears all are now focused on new ventures, including advising, investing in, or launching startups, mirroring a growing trend among former Shopify executives and staff.

A Natural Outgrowth of Success

Given Shopify’s substantial size – a 15-year-old, 7,000-employee organization based in Ottawa with a $130 billion market capitalization – this level of outward movement isn’t entirely unexpected. However, the considerable wealth generated by Shopify positions its former employees to significantly impact the Canadian entrepreneurial landscape in a way no other company has before.

Investing in the Future

Consider Craig Miller, previously Shopify’s Chief Product Officer, who departed in October. While still employed full-time, he was already involved in venture funds concentrating on clean technology and Canadian ventures. Now, he is dedicating both his capital and time to companies he believes “have a genuine opportunity to create substantial positive social change.”

His investments encompass tools empowering individuals to establish and manage their own businesses, such as Housecall Pro. He is also backing startups dedicated to mitigating climate change, including Planetary Hydrogen, a carbon capture innovator.

The Value of Experience

Miller emphasizes that his experience is highly valued by founders, many of whom are former Shopify colleagues. “Securing funding is crucial, but there’s ample investment capital available,” he explains. His primary contribution lies in advising teams on scaling their startups, drawing upon his experience in guiding a company from a $100 million valuation to over $100 billion, and understanding how to expand a product to millions of users.

He notes that individuals with this level of hyper-growth experience are rare, particularly within Canada, “where there are comparatively few established role models.”

A Culture of Learning

Miller attributes his skillset to the environment fostered at Shopify, highlighting the company’s commitment to employee education, even if it was largely informal.

“A key aspect was our transparency,” Miller states. “All employees had access to the product roadmap, the codebase, and company data. We even shared our board presentations company-wide. This allowed those interested in building a successful company to learn from our experiences.”

From Employees to Entrepreneurs

Numerous individuals who have left Shopify have gone on to launch their own businesses. These include Michael Perry, creator of the family organization app Maple; Helen Tran, founder of Jupiter, a software provider for beauty and personal care brands; Andrew Peek, who established the investment advisory firm Delphia; and Effie Anolik, whose startup, Afterword, assists individuals in planning memorial services.

The "Shopify Way"

Arati Sharma, a former Director of Product Marketing and a proud Shopify alumna, describes the company as a “unique environment” that taught many how to scale a business, and to do so in a distinctly Shopify-centric manner.

As the first company of its scale in Canada, Shopify lacked pre-defined notions of how large organizations should operate and wasn’t constrained by traditional business practices, empowering employees to innovate and discover solutions.

The Founder's Journey

Sharma acknowledges that the Shopify experience, while valuable, has limitations when applied to launching her own company, Ghlee, a Toronto-based ghee-based skincare brand founded in 2019. “While I had the opportunity to build from the ground up within Shopify, being a founder presents a completely different set of challenges,” she says.

However, like Miller, Sharma credits Shopify with imparting crucial lessons, particularly “how culture and commerce are deeply intertwined.”

She also points out that “whether you join Shopify as an established founder or develop an entrepreneurial spirit while working there, a remarkable number of employees ultimately start their own businesses.”

Side Hustles and Investment Firms

Some are even pursuing entrepreneurial ventures while continuing to work at Shopify. Atlee Clark, for instance, founded Pika Layers, a children’s clothing company, while remaining a full-time director at Shopify.

Others have established investment firms after leaving. Adam McNamara, a former VP of Product, now leads Ramen Ventures, an impact angel fund, alongside fellow Shopify alumnus Joshua Tessier.

Investing in Women

Notably, Sharma is also an active angel investor and co-founded Backbone Angels earlier this year, a collective of 10 investors focused on “accelerating deal flow and quickly capitalizing on promising opportunities.”

All members of Backbone Angels are women, all are former Shopify employees – including outgoing Chief Talent Officer Brittany Forsyth – and all are dedicated to increasing female and non-binary representation on cap tables, believing this will reshape board compositions and company building practices.

A Thriving Ecosystem

Partly due to Shopify’s success – its share price experienced significant growth last year, although it has since seen fluctuations – there is a wealth of opportunities for investment.

Sharma, who began investing with her husband, notes that of the over 30 startups she has funded, nine of those deals were completed just this year.