Gena Sherwood’s inspired career: A story of passion, support and impact

I’m Gena Sherwood, a Lead Client Partner based in Toronto, and I’ve been at Pinterest since 2019. In this blog, I’ll discuss how impact is deeply embedded in Pinterest’s values, as well as my own, and how I’ve been championed and supported in my ambitions to create positive change.

Transforming passion into opportunity 

I joined Pinterest in 2019, a few months after the Pinterest Canada team was first founded. 

From my very first day at the company, my leadership team encouraged me to show up as my true and authentic self – undiluted, unfiltered and unapologetic. They valued me for the fullness of my experiences – not just my professional accomplishments. That wide net of support and empowerment gave me the confidence to pursue my passions, both within my role and outside of it. 

I have never been one to confine myself to the parameters of a job description. I spent the first half of my career leading Consumer Marketing, and though I now work within Sales and Partnerships, I’m not afraid to flex my creative muscles and to push the boundaries of what’s expected of me, whether that’s by pitching big ideas internally, or creating and leading experiential activations and events for the brands we partner with. That fearlessness has enabled me to broaden my impact, and to build a meaningful and fulfilling career at Pinterest. 

Inspiring work-life balance and support

My team at Pinterest rallied around me through some of the most trying and difficult moments of my life. I’m a mother to two beautiful, exceptional children. But unfortunately, they both had rough starts, with health battles early on that required the full range of my attention. Pinterest accommodated me through those challenging times, allowing me to focus fully on being a mother when my children, and my own health, needed me the most.

When I returned to work after several months of unexpected bed rest during my pregnancy shortly followed by a long hospital stay with my newborn, I felt slightly unsure of myself. I’d spent so much time away, and my confidence was wobbly, self-doubt slowly creeping in. But my team approached my return with excitement – and an opportunity. A senior team member whose work I’ve always been incredibly inspired by, was being advanced into a new role; and the team wanted me to step in as their backfill. That validation was critical, their belief energizing me to step back into my power and confidence.

Since then, I’ve been tapped to take on a broader role as Lead Client Partner, and had the privilege and honour of being accepted into Harvard Business School’s Women’s Executive Leadership program as part of the 2025 class. This opportunity was possible thanks in large part to the recommendation of my team, who have championed me from the outset of my career. Since completing the program, I’ve delved so much deeper into my capabilities as a leader and feel more empowered and prepared than ever to deliver impactful work and create meaningful change in the world.

Creating positive change

I’ve been fortunate to build a career I’m proud of — and in many ways, it still feels like just the beginning. One moment that shaped my journey early on came while I was working in one of my first marketing roles, when a CMO encouraged me to create a personal mission statement to identify what I really wanted out of my career and help serve as a compass. I wrote that my mission is to always be a consumer-centric thinker who positively impacts my team and the world around me. While many of my goals have evolved and grown with my career, my purpose, in both life and work, is still to make a difference and to leave the world in better shape than I found it. Working at Pinterest has empowered me to chip away at that mission, in a plethora of beautiful ways.

In 2020, I recognized that Black employees in Canada needed space to connect, grieve and be in community with each other, so I brought Blackboard programming to Canada. I also spearheaded local initiatives for other communities, such as Women@, Asians@ and others to ensure that everyone felt the same sense of inclusion and belonging.

I also collaborated with the Creator team to include Canada in the Creator Inclusion Fund, a program to support and encourage creators to get started on Pinterest. It also had a mentorship aspect that connected small business owners with members of our local leadership team, who offered onboarding advice and best practice guidance.

In 2025, I became a Co-Lead within Pinterest’s Impact Ambassador program which focuses on volunteerism initiatives, as well as designing programs to support underserved communities through care packages and other purpose-driven campaigns.

I'm also grateful for the opportunity to volunteer as a mentor, offering advice and support to early/mid-career professionals and students hoping to break into a career in marketing. I intimately understand the value of having people in your orbit who recognize and nurture your potential – I attribute much of my own success to my mentors, who gave me the template for how to show up. It's not lost on me how meaningful it is to be in this position, where I'm able to pour what I've learned into future generations and help guide them on their own paths. It's a responsibility I bear with care and intention, and that I hope to keep growing into. For me, legacy isn't just about what you build, but the mark you leave on others, too.