International Women’s Day 2022: Building workplaces where women thrive


The theme for International Women’s Day (IWD) 2022 is #breakthebias, which focuses on creating a gender-equal world that is free of bias, stereotypes and discrimination, and that celebrates diversity, equality and inclusivity.

At Caravel, we’re committed to championing the women on our team and in our community. We’re especially dedicated to supporting women entrepreneurs as they break barriers and work to enhance equality in the workplace. 

Our co-owner, Jackie Dinsmore, has been instrumental in supporting women lawyers and entrepreneurs and has led by example in her own career. As a lawyer, Jackie has worked at one of Canada’s leading corporate law firms and has also served as Associate General Counsel at a leading media conglomerate.  

As a businesswoman, she launched and sold a successful consumer product business and has played a pivotal role in strategy and business development with both Cognition and now Caravel. Today, in addition to serving on the Caravel board, she is a board member for a number of charities and organizations that aim to improve the lives of women across the globe. 

We sat down with Jackie to discuss her experience as a ”serial entrepreneur” and how she and the team at Caravel are working together to build a more inclusive workplace for women.   


What was the biggest challenge you’ve faced as a woman in your professional career?

Well, there have been a few. When I went on maternity leave as an in-house lawyer, there weren’t many options for filling my role. For my first maternity leave, my employer split cover between two lawyers from an outside firm. It was time-intensive and inefficient to onboard and train each of these lawyers, but that was really the only option. It was incredibly stressful on the organization and my team, and I felt a lot of personal guilt for taking time off and questioned whether I should come back early to help. At the time, there really weren’t any programs for supporting working mothers, especially in the legal profession. 

While I was on my second maternity leave, I started a consumer products company with my mother. We worked with factories in China, and there were many times that I wasn’t allowed to speak to the factory owners. Even though I was the founder of the business, they would only talk to my father or husband because they were  male. Things have changed a lot since then, but it was incredibly difficult at the time to be so openly discriminated against – especially given that I was running the business – simply because I was a woman. 


Given the theme of IWD 2022, how do you believe workplaces can help #breakthebias for women? 

I’m a firm believer in the importance of mentoring, and I think women leaders and entrepreneurs have a lot to offer the up-and-coming generation of professionals. When I first worked on Bay Street, I found there wasn’t a lot of support for younger women, and it’s something that would have helped me so much while I was starting out in my career. As women, I think it’s crucial that we lift each other up and provide help and advice to those who are younger and less experienced. 


How are you and Caravel working to support women in the workplace and the wider community? 

On a personal level, I’m a World Vision Power of Her Impact Council Member, a gender equality initiative that seeks to break the cycle of malnutrition for women and girls to improve their health (specifically maternal health) and well-being. I’m also a board member for Opportunity International Canada, a global non-profit organization that provides micro-financing to both women and men in developing countries to work their way out of poverty and build profitable businesses. 

When we first started the business (then Cognition LLP), a large part of our success was providing a flexible and supportive work environment in the legal industry for women lawyers who felt displaced. In fact, the first nine lawyers we hired were women. As part of our hiring practices at Caravel, we’re committed to recruiting women who have taken time off to raise their families. We understand that the legal profession hasn’t always been accommodating to professionals who have taken this break in their careers. At Caravel, we’ve made a conscious decision to support and hire lawyers who want to re-enter the workforce after taking leave. 


Is there a woman who you find inspiring who you believe #breaksthebias?

We learned about the Supreme Court Justices in law school –  and if I had taken a different path in my career, I would have loved to be a judge. There’s a well-known Canadian judge named Beverly McLaughlin who has long since retired, but I would read about her judgments with so much respect and admiration. She became the Chief Justice of the Supreme Court of Canada, which is pretty amazing. To live in a country where a woman not only sits on the highest judicial body in the nation, but also becomes the highest-ranking judge in our entire court system, is incredibly inspiring. 


IWD 2022 takes place annually on March 8th. To learn more about #breakthebias and the IWD mission, visit

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