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Vince De Freitas (MT '17), the son of two teachers with a combined 80 years of teaching experience, always thought he would work his way through the public education system. But a future relationship – with his wife – who worked at tech startups, inspired Vince to merge his love of education with a passion for technology outside of the classroom.

Vince recently joined Shopify as their Merchant Education Lead. His team helps merchants scale their businesses from something they do out of their garage to something bigger.

With more than a decade of experience teaching, coaching, consulting and learning, Vince likes to say he turns coffee into education.

Tell us about your 'OISE origin story'. We'd like to hear what you found meaningful during your student experience?

I was struggling to reach a deadline during my second year in the Master of Teaching program. Life was chaos, I was working part-time after class and had to fill big shoes for a manager who had recently received a cancer diagnosis. This affected my work, but my OISE supervisor was patient and kind. He gave me the time and space to complete my research draft properly. I’m extremely proud of this work.

"I’ll never forget how my OISE teacher considered the human behind the student"

It’s a moment I think back to often when faced with learners who may be struggling with factors outside of the learning environment that we can’t control. I'll never forget how my OISE teacher considered the human behind the student.

Who else in the community really inspired you?

Big shout-out to Cristina Guerrero! She was my instructor in multiple classes throughout my program and I was always inspired by her journey from the classroom, to OISE, and back to the classroom. I feel like a lot of new teachers have difficulty seeing the transferability of their skills, or imagining how they can steer their own career in what otherwise feels like a predictable field like education.

And when did you discover this passion for education? What caused you to pivot from teaching to education business?

It’s no surprise to anyone who knows me that I would land in education. I’m the son of two teachers whose total lifetime experience in-class lands around 80 years. For a long time, I only imagined myself climbing through the school system chain of command, from teacher to administrator to working in the school board.

"I found an opportunity to merge my love for education with my digital-native experience in technology. With [my wife's] help navigating the startup world, I landed a full-time role...at an ed tech company"

I actually owe my pivot to enterprise education and technology to my partner Lauren, who I met while completing my master's, and who typically worked in startup tech companies. As the 2017 job market looked tight, I found an opportunity to merge my love for education with my digital-native experience in technology. With her help navigating the startup world, I landed a full-time role at Top Hat, a Toronto-based ed tech company for higher education. There, I spent 3 years working in – and eventually leading – the instructional design function until I left to join Nelson Education, a K-12 educational publisher. I spent two years at Nelson and was leading product management and marketing for math and science before and into the COVID-19 pandemic.

I think we all know how taxing the pandemic has been on K-12 schools across Canada. I was excited to take a step away from the curriculum space and join Shopify late in 2021 to focus on educating new entrepreneurs on navigating the world of small and medium business.

Congrats on your new role at Shopify! Tell us about it. What do you bring to this role?

My work at Shopify is largely concerned with merchant experience and education. I lead a small team of four talented folks, and we help merchants navigate the world of fulfillment as they scale their businesses from something that they can do out of their garage, into something bigger and grander.

Education is only a small part of this type of work. As a lead, my priority is the effectiveness and wellbeing of my team. Many other teams support merchants here at Shopify – cross-functional alignment and communication are vital to our success. I spend a fair bit of time gathering context for wider teams and helping to upskill folks to think about and execute educational experiences for our merchants.

You're versed in enterprise education. What impact have you always wanted to make in this field?

I think technology is a game-changer for education and I love being able to play a role in that shift, whether it’s for K-12 or adult learners. But I also recognize that before the pandemic, technology never needed to play a large role in our classrooms, as there were (and still are) many equity concerns about access. That said, I’m the proud uncle of an eight and four year old. I maintain that if they get to high school and have largely the same experience that I had >20 years prior, then we have collectively missed the mark and are failing to prepare our students for the world they are entering into.

You’ve been an active OISE Mentor and enjoy staying connected with U of T. Can you share what motivates you, your mentoring style, and what you've learned from your mentees?

The OISE Mentorship Program experience has been a terrific way to give back and help create in-roads between the educators of tomorrow and the professionals of today. When working with graduate student mentees, I enjoy taking a step away from structure and focusing on the relationship. While structure is helpful, in my experience some moments exist outside of it that can be missed if you over-rely on an agenda.

At the end of the day, mentorship is about creating and maintaining a human connection. I try to really get to know my mentees and challenge them to think bigger and imagine what they are capable of beyond the current box that they think they are in.

"Everyone must have a cheerleader in their corner who will unrelentingly say 'Yes, you absolutely can get there, and maybe even further. Let’s chat about what that might take'"

From mentoring, I’ve validated my opinion that self-assessment is truly some of the least meaningful assessments when thinking about your career. We hold too many insecurities and fears from past experiences that often make us think or dream too small. That said, not everyone wants to, or needs to go huge especially when there are many other important things in life. But everyone must have a cheerleader in their corner who will unrelentingly say “Yes, you absolutely can get there, and maybe even further. Let’s chat about what that might take.”

Speaking of mentoring, what's your advice for students interested in pedagogy?

My mother has always said, "there’s nothing really new in teaching," and she’s been teaching for more than 40 years across three countries with unique and distinct education systems. I think there’s something to that.

"You’re going to find that there’s always a common thread of student-centric learning design that runs the entire way through"

I think it's important for folks to remember that good teaching is good teaching. Every few years, you’re going to find that there’s a new initiative, new jargon, new framework, etc. The longer you spend looking at them, the more you’re going to find that there’s always a common thread of student-centric learning design that runs the entire way through. Don’t marry yourself to a single framework or system of thinking, and focus instead on why the framework exists and is effective. Look for the through-line to the underlying concept. You’ll find trends more easily this way.

On the flip side of this, recognize that there are absolutely new tools that can augment how we conduct instruction, and more importantly can help us evolve in our roles as teachers. Facilitation of learning is the new direction in my view, and technology can help us redefine our roles within the classroom, providing more equal footing to all students. That said, we’re still in our infancy with this type of work and we must be patient as the ecosystems find their footing. Don’t be afraid to be a part of this change, but recognize that your biases and view of the system are currently limited by the scope of the classroom. You must think bigger and wider.

With OISE I Can...

"Start on a journey toward the type of educator I want to be."

Vince De Freitas is a mentor in the OISE Mentorship Program. Want to connect with him? .