Shopify VP, Assisant GC Erin Zipes on Lawyers as Entrepreneurs

Erin Zipes is currently Vice President, Assistant General Counsel at Shopify, where she originated, built and scaled the corporate legal function from pre-IPO (NYSE and TSX) to present. In addition to leading the corporate legal team at Shopify, she currently leads the commercial/product counsel team on an interim basis.

Erin has over 16 years of experience as a corporate/securities lawyer, 11 years of which as Assistant General Counsel for cross-listed public companies. She was previously Assistant General Counsel of Nordion (formerly NYSE and TSX), and started her legal career at Stikeman Elliott.

Erin is a founding member of Backbone Angels, a collective of angel investors investing in women and non-binary founders. She also acts as Advisor, Partnerships and Overall Strategy, to Heirlume, an AI-powered trademark registration start-up.

Erin lives in Ottawa with her husband, two children and dog.

Counselwell: Describe your background and how you became the Vice President, Assistant General Counsel of Shopify.

Zipes: I went to business school (BComm at Queen's University) with the intention of going to law school afterwards and becoming a corporate lawyer - 20+ years later and I have stuck to that plan! After McGill Law I started my legal career on Bay Street at Stikemans, where I had a practice mainly focused on capital markets transactions and private M&A, with some banking, corporate governance and regulatory work in the mix. I then moved back home to Ottawa with my family and worked at Gowlings for a year before following a partner in-house to a health sciences company called Nordion. It was a small company but was cross-listed on the NYSE and the TSX and so was an ideal place to get my footing as to how to work as in-house counsel, which can be a difficult transition from working at a firm. In my 3 years at Nordion I helped them sell off a major business unit and complete their going-private transaction.

By that time I had met some of the folks at Shopify and convinced them that I could help them with their IPO and beyond. I joined Shopify as Assistant General Counsel in September 2014 and in May 2015 Shopify became a public company. I've been privileged to witness and support Shopify's exponential growth and evolution and gone through my own in parallel. These days, while I still very much enjoy law and the practice of law, I'm much more of a leader than an individual contributor. The Shopify legal team has grown over the years and continues to scale to meet the needs of Shopify so I've had to keep up.

Counselwell: You recently launched a new angel investing group with your Shopify colleagues called Backbone Angels - congrats! Can you tell us about it?

Zipes: Absolutely! Backbone Angels is a collective of angel investors - so we're not a fund or a syndicate. Basically that means we work together to source and diligence deals but then make individual investment decisions as to whether or not and how much we'd each like to invest. That said, we collectively support every founder in our portfolio, which is one of the parts of Backbone that I enjoy the most. I love getting to meet a variety of founders, hear their stories and learn more about the problems they're trying to solve, and share with them the wealth of experience and knowledge that I've been privileged enough to amass over my career to date. Between the 10 of us we have expertise in product, data, UX, marketing, talent, culture, legal, operations and strategy, and we've all survived and thrived in the chaos and challenges of hypergrowth. Getting to spend more time with 9 of my favourite kick-ass women is also one of my favourite parts, especially as some of us are starting to move on from Shopify, so this gives us the opportunity to stay connected and working together. Spending time advising founders is also a really fun way for me to pay forward some of the incredible luck and privilege I've had in my career.

Counselwell: It’s not often that lawyers launch “side hustles”, presumably because of how all-consuming a legal career tends to be. How do you balance your work at Shopify with Backbone Angels?

Zipes: As a working parent I've had 12 years to figure out how to balance work and parenting - both of which can be all-consuming at times - and now that my kids are a bit older I have some more time to dedicate to a side hustle. Real talk though - I don't really have hobbies and I have an incredibly supportive partner who is a true co-parent and does more than his fair share on the home front. I find angel investing and advising founders to be really energizing and fulfilling, so it's a great complement to my day job. Sometimes a change is as good as a rest, right?

Counselwell: What advice do you have for lawyers who are working full time but also thinking about doing something entrepreneurial?

Zipes: I think there's a belief held by many that lawyers are not natural entrepreneurs, but I haven't found that to be the case. Many law students and lawyers that I meet are so entrepreneurial and really counter the traditional, by-the-book, anxious lawyer stereotype. If you're considering doing something entrepreneurial my advice is that it's often easier to take big risks early in your career, when it's easier to pivot if needed. It's also easier when you're only responsible for yourself, it gets more difficult when you're supporting or partly supporting your family. Lastly, I think entrepreneurism isn't necessarily a trait that folks either have or don't have, I think for many it's a muscle that can be developed over time. There are tons of founder groups out there looking for good advisors, and getting to know founders, providing them with legal advice - either informally or formally - could be a good way to dip your toes into that world.

Personally, I would have never considered myself to be a risk-taker or entrepreneurial in the least, but my career to date has really stretched me far outside of my comfort zone and forced me to develop my abilities to assess, mitigate and tolerate risk; process huge amounts of data from noise into signal and make decisions with imperfect information; and work closely with a variety of people and functions. All of these skills are hugely valuable to an entrepreneur. The most important thing I've learned so far is that I get to keep evolving and developing, so I don't put limits on myself anymore in terms of what I think I can do or accomplish.