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How I Made It

How I Went From Selling Textbooks to Leading a Top Edtech Company

Education has been the driving force in Maggie Leen’s career—and as CEO of Top Hat, she’s continuing to reimagine how students learn in a digital-first world
Maggie Leen, CEO of Top Hat.
{Photography: Top Hat}
By Maggie Leen
Sep 12, 2025

I come from a big, noisy family. As the oldest of four siblings, I quickly learned that the loudest voice doesn’t always win—the most patient one often does. I learned to lead by listening. 

Growing up, education was the cornerstone of my family’s values. My grandmother, a dedicated teacher in the Detroit public school system, often told me, “Education is yours forever. Once you have it, no one can take it away.” Those words stayed with me, and education became my north star. 

My paternal grandfather enlisted as a medic in World War II solely so he could attend college. After the war, he became a doctor and opened a practice down the street from his house. Inspired by him, I volunteered at a local hospital in high school, then later enrolled in a science and psychology program at Marquette University. But after my first encounter in an anatomy wet lab with real cadavers, I realized medicine wasn’t the path for me. 

Still, I knew I wanted to help people. I began working at a domestic violence shelter after university, running programs for survivors and their children that taught everything from parenting skills to opening a bank account. It was here I saw how education—basic financial literacy, dietary needs, and job application support—could give someone not just knowledge but the confidence to rebuild their life.

When my husband’s military career brought us to San Diego, I joined Pearson as a sales representative. Originally a textbook publisher for K–12 and higher education, Pearson has grown into the world’s leading learning company. I loved helping professors support their students in mastering complex concepts, which I once struggled with myself. 

Fifteen years at Pearson flew by. During that time, I had my twin daughters and rose from an entry-level sales rep to senior vice president of marketing by listening to what students and educators needed. As Pearson evolved beyond textbooks into digital learning, it was thrilling to see technology bring complex concepts to life—like virtual anatomy labs where students could explore a 3D heart or examine a cow’s eye from every angle. I watched barriers to learning disappear and wondered what else was possible. 

In 2019, I became vice president of marketing at Adtalem, joining a women-led team focused on healthcare education in the U.S. and the Caribbean. Our mission extended beyond recruitment–we aimed to expand access to education, helping aspiring healthcare professionals advance their academic journeys and serve their communities. 

In 2021, Top Hat—a Toronto-based edtech company—approached me to join as chief marketing officer. Though initially hesitant to leave a mission I loved, they recognized the value of my broad perspective shaped by my experience creating educational materials and understanding institutional needs. What ultimately convinced me was the chance to confront  higher education’s toughest challenges, such as high dropout and failure rates, the human cost of unfinished degrees, and the urgency of keeping learning relevant in a rapidly changing world. 

I first learned about Top Hat during my Pearson days. In 2009, University of Waterloo students Mike Silagadze and Mohsen Shahini launched the start-up from their apartment, with the goal of creating a more accessible, participatory learning experience. The result was Top Hat—the first platform allowing students to engage with course material in real time using their own devices for polls, quizzes, and interactive features during lectures. 

I eventually took the leap. After years at large, publicly traded companies, joining a smaller, privately held business with limited resources felt like a welcome challenge. I saw an opportunity to strengthen Top Hat with a more focused sales and marketing strategy that better connected its products to customer needs.

What drew me to Top Hat was its innovative authoring tools, allowing educators to adapt digital textbooks—customizing content to reflect students’ backgrounds, interests, and needs to make learning as relevant as possible. I hadn’t seen such responsive educational technology before, and it felt aligned with the growing demand for personalized learning in a rapidly changing world. Today, Top Hat is the leading student engagement platform in higher education, giving educators the tools to create interactive lessons and assignments, track progress instantly, and provide students with a centralized hub for participation, practice, and feedback. 

When Top Hat’s CEO stepped down in 2023, the board asked me to serve as interim. By March 2024, my appointment became official, and I asked to share the news on International Women’s Day. Becoming Top Hat’s first woman CEO was a proud milestone, made unforgettable by having my daughters watch the Zoom announcement from home. Later, colleagues told me they showed the video to their own daughters—a reminder that this moment wasn’t just mine; it belonged to all of us. 

Working with the team, we set out to build on the company’s foundation, starting with restructuring sales. Previously, reps were mostly remote so someone in Toronto might cover all of British Columbia. But ours is a relationship-based business, so we assigned reps more closely with the roughly 1,500 institutions we served. The payoff was immediate—in one case, after relocating a strong inside sales rep to their territory, they quickly became our top performer.

We also revamped goal-setting and staff compensation. As a former sales rep, I knew how crucial it was to align incentives with the realities of the role. With these changes, and by focusing more on customer retention, we had our best fiscal year yet. Customer service issues decreased, and our net promoter score increased to 51 per cent—the highest in Top Hat history. Our retention rate held steady at 90 per cent, with a six per cent year-over-year increase, reflecting the enduring value Top Hat delivers to customers.

A key part of our success has been moving quickly to tackle longstanding challenges in teaching and learning. Research shows that one-on-one tutoring significantly improves student outcomes, so we launched Top Hat Ace–an AI-powered assistant that offers instant support, including easily digestible explanations, and unlimited practice questions tied to course content. Ace also provides targeted practice based on areas where a student is struggling, helping them prepare for mid-term and final exams. 

It hasn’t all been smooth. Before my appointment as CEO, I led a major restructuring of Top Hat that included laying off 10 per cent of our workforce. We needed to streamline roles, and we weren’t as efficient as we needed to be. It was one of the hardest things I’ve ever done. 

Related: How Martin Basiri is Helping to Solve Canada’s Labour Shortage

Since then, I’ve prioritized greater transparency across the company. We now share revenue numbers openly with staff and hold financial education sessions to help them understand the business. With a team of about 325—over half based in Canada—I make it a point to connect with as many employees as possible. If I can’t meet face-to-face, I’ll send a quick Slack message, even just to say, “Great job.” I believe these moments of recognition are what keep everything moving. People need to feel that their work matters and that it’s making a real impact on the company’s success.

Today, over three million students, 35,000 instructors, and 1,520 institutions across North America use Top Hat. In our recent survey of 21,430 students, 91 per cent said they’d recommend Top Hat to their instructors. To top it off, we’ve climbed into the top 25 per cent of the fastest-growing edtech companies. But for me–and many of us–what’s truly motivating is knowing the work we do is opening doors, transforming futures, and changing lives. Driving better teaching and learning for a brighter world is our true measure of success.

– As told to Lindsey King

Maggie Leen
Maggie Leen
Maggie Leen is an accomplished executive with over 20 years of leadership experience in higher education, including sales, business development, operations and marketing. Prior to joining Top Hat, Maggie held a variety of progressively senior sales and marketing roles at companies such as Adtalem and Pearson.

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