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West Point Grey Academy With Stephen Anthony, Head Of School

By June 6th, 2024No Comments16 min read
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Discovery Pod | Stephen Anthony | West Point Grey Academy

Welcome to today’s segment of Opportunity Spotlight with the Discovery Pod, where we highlight incredible leadership roles within organizations in the social profit sector. Join us as we sit down with Stephen Anthony, head of West Point Grey Academy, to explore the values, culture, and leadership of this vibrant independent school located in beautiful Point Grey, Vancouver. In this episode, you’ll gain insights into the Director of Advancement role, the school’s remarkable growth, and its commitment to creating a warm and welcoming community. Whether you’re an experienced advancement professional or simply curious about this exciting opportunity, discover if you’re the right fit to join a team dedicated to shaping lives of inquiry, action, and joy.

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West Point Grey Academy With Stephen Anthony, Head Of School

I’m excited to talk with Stephen Anthony, the Head of West Point Grey Academy in beautiful Point Grey Vancouver. Welcome, Stephen.

Pleasure to be here.

West Point Grey Academy

Pleasure to speak with you. Stephen, we’re going to be talking about the Director of Advancement Role at West Point Grey. Before we get to the specifics of the role and specifics of what that person’s going to be doing, let’s talk a little bit about your school. Let’s talk about the great West Point Grey Academy. Tell me a bit more about it for someone that may not know too much about it.

I like that you’ve added the great West Point Grey Academy. We may have to put that in our tagline.

I’ve been meeting with some of your staff and parents. They’re a pretty great group.

I’m a very happy and very humble head at West Point Grey. I’ve been here since our inception in 1996. I’ve had the good fortune to see our growth from that idea in ’95 and ‘96 to what we are now. I’d still describe us as a relatively young and very vibrant school. There’s a happy and notably friendly climate that our families and our visitors tend to clock the minute they come on to the campus or even enter the buildings.

In 1996, we began as a small nonprofit independent day school. We wanted to be a place where families could enroll all of their children. Now, we’re at full capacity, 940 students in grades JK-12. By intentional creation, I’d say, we’ve enjoyed remarkable exponential growth even in our size, sophistication, the school’s reputation, achievements, and our potential.

When at school being only 28 years old, maybe back when I was that age. I’d say that it feels like we’re in our prime. We’re not an organization or an institution that’s laden with 150 years of tradition and history. That allows us to have this young spirit to be progressive, nimble and focus our vision onto the future.

I’m glad you brought that up. I certainly feel that when I’m in the halls or on the grounds of the school for that matter, that palpable, tangible warmth, and feeling of community. Is that what you think makes West Point Grey unique?

We are part of an association in BC of 27 independent schools then across Canada. The case association is 96 schools. The executive directors of both of those associations have said time and again when they come and visit this school, they recognize that first and foremost, it’s happy, warm, and welcoming. There’s a real spirit here. When I’m hearing from others that have those comparatives to these other great organizations across the country, it does make me realize that by intention, that’s what we’ve created and other people are feeling it.

I love that intentionality. It needs to be deliberate. When it’s deliberate, it comes across. It works fundamentally. What is your why, Stephen? Why is it that you do the work you do? You’ve been in the education space for so long. You’ve been at West Point Greys and its inception. Why?

One of the things I’ve enjoyed specifically about being here is there’s this thin layer of red tape that exists between the genesis of an idea and its implementation. It allows us to be creative and excited about the possibilities and what can be. Not unlike a modern-day electric vehicle. This is the place where I come every day to recharge my own batteries. Whether it’s with the kids or my colleagues or the parents, that happens every day and it’s unique.

It’s spirit lifting. We’re building authentic relationships among the people that are here. The other thing is I recognize that the good work that we do while we’re in this present moment is something where you get a sense of the investment of that time and energy is going to have a wide-ranging and a positive impact down the road in the future. Knowing the work that we do is both rewarding and gratifying in the moment. When I connect with my alumni families, my alumni students and recognize the impact that it’s had later on down the road, makes it all worth it.

The good work we do in the present moment is where you get a sense that the investment of time and energy will have a wide-ranging and positive impact down the road. Click To Tweet

That long-term vision, the echo, the shout out. The effects of an education are so important.

You got it. As you know and appreciate yourself, being in a school environment, every day is unique. I’m interacting with 5-year -old and 18-year-olds across the student spectrum. I’m engaged in deep philosophical and social justice conversations with our teens. I’m in the sweetest and endearing moments of those younger students on their journey. It’s a great thing to be a part of.

You’re also dealing with engaged parents, board members, and volunteers at multiple levels. I’m sure we’ll talk about them in the future as well but they are essential to the community at large, aren’t they?

That’s right.

Stephen’s Work At West Point Grey

What are you proudest of having achieved so far at the school? You’re a young man. There’s still some years to go in your tenure but you’ve achieved so much already in your work with West Point Grey. What are you most proud of when you think about your time at the school?

I noticed, by calling me a young man, you’re not wearing your glasses at our meeting. I’ll say thank you and forgive you for that. I’d say it’s this chance that I’ve had to work alongside so many amazing people, board volunteers and parent volunteers and staff and to help grow the school from this idea to what we now know as a world renowned leading educational institution. That’s allowed that wolfpack pride to run deep.

We’ve always been a school that looks for opportunities to be creative and to improve. Never resting on our laurels, always thinking of how we can do this a little bit better, whether it’s our programming or facilities. That means then increasingly in my role, I’ve had a chance to be engaged with donors who are fully enamored by the possibility and the opportunities of the school.

Discovery Pod | Stephen Anthony | West Point Grey Academy

West Point Grey Academy: West Point Grey has always been a school that looks for opportunities to be creative and improve. We never rest on our laurels, constantly thinking about how we can do things a little bit better, whether it’s our programming or facilities.


In recent years, we’ve come together on a number of exciting projects. We fully renovated the main gym. We fully funded a new gymnasium, learning commons in student resource centers, the Dining Hall, and the campus trail. We’ve got a leading Indigenous education plan, scholarship and financial assistance programs. Recognizing that the work in this space of philanthropy and advancement has been gratifying to make changes to the school. For both the programs, the people and the place.

West Point Grey Culture

Let’s pivot in that direction then, thinking about working at the school, work culture. Many candidates, many people in the space ask me about work culture. We’ve talked about the school’s culture and the feel you have in the room, but what’s it like to work at West Point Grey? What’s the culture you’re trying to create as the head of school fundamentally among your staff?

The earliest questions posed by our founding headmaster were, “What do you want to be involved in? What difference do you want to make? What impact do you want to have or stamp you want to be able to put on this place?” I’ve made sure to take that and ask that same question of the people that come and join us.

I want them to make sure that there’s a genuine sense of belonging. That they feel valued. It’s a place where you know your voice is important, encouraged, and heard. Your solutions aren’t just welcomed but we want them, expect them, and value them. That helps us create this can-do community where you’re engaged. It’s extremely collaborative. You never feel like you’re alone in doing this work in this place. There’s space for you to do the good work on a project that you’re working on by yourself. At any given moment, you can have a number of team members around you to support you in the work that you’re doing and feed off each other’s energy and creative ideas.


I was going to ask you about how people come together and how that collaboration happens but you’ve anticipated that question in some ways. That’s great. Let’s pivot about two advancements, I should say. Specifically, the director of advancement recruitment that we’re working together on. What is exciting about advancement at West Point Grey? What’s coming up? What’s on the horizon that this person’s going to be getting to work on?

It’s the thing that as a young institution, for so many of us, it was something we did off the side of our desk. As we’ve grown in sophistication and evolved, we’ve realized there is the need for somebody who lives and breathes this work, knows it, and understands it and how to engage with families who want to donate their time and their treasure.

We have a number of key teams at the school. We’ve got our junior and our senior academic leaders, then we have BizOps, which is our business and operations. Advancement lives within ACE. ACE is the acronym for Advancement, Communications and Enrollment, then we have our board of directors that’s super engaged that’s supporting all of us. We came together in August. We do a goal setting retreat in August, then we meet throughout the school year one-to-ones. With our fuller leadership team to advance all the strategic priorities that we have.

In our earliest days, we were very sensitive to building a new school, a new independent school. Coming together as a sense of team amongst our parents as partners. Everybody was rolling their sleeves up and volunteering for playground duty and library duty and so on. We had a nascent idea about what advancement could be. More recently in the last number of years, it’s been something that’s blossomed at the school.

What I’ve been excited about is recognizing that parents are waiting for this. They’re hungry. They want to be informed. They want to be inspired and motivated. They’re contacting us and saying, “How can we help? What do you need? What’s a project?” Whether it’s my wisdom and experience, my company, my time, or a major gift to help the school move forward in all of those different areas in programming and facilities and what a difference it’s made.

Even when the alumni come back and come into the building themselves. These are 60 to 70 year old buildings that we inherited by these thoughtful improvements and renovations we’ve made on the inside. They say it’s almost unrecognizable. You notice and you see what a difference that makes for how the students show up. Now, we’ve given them a study space or a work space or a meeting space. We’ve done renovations around the campus and our outdoor spaces as well. It changes the way we can interact with each other.

I’m glad you talked earlier as well about the subject matter expertise and recognizing that this is a specialized skill set. It requires somebody that has the knowledge and the experience to do the work and build these relationships and engage parents that are clearly wanting to do more. Those conversations with parents have shown that to me as well fundamentally. That’s great.

If I move from there, I’d say that we’re at an exciting stage of our evolution. We’re approaching 30 years. We have developed a culture of philanthropy. We have an annual gala for fundraising that our most recent one raised over a million dollars in one evening, one event. We have our Giving Tuesday event in late fall. We have a number of other smaller events throughout the year where there are opportunities in the advancement world for us to engage with the families.

We’re also on the precipice of preparing for the next iteration of our school and starting to talk about building the case for support and the framework that we require for a campaign to eventually fund the new building. It’s going to be complex. It’s going to be fascinating. It will be something probably unseen across the Canadian landscape given the size of the development in the surrounding area and our part to play in it. Not being a school that might be raising funds to build a wing or a tennis court or a gymnasium.

If we’re building everything from scratch, you can imagine the magnitude of the work that’s going to be required and the exciting part that’s going to create for us. Having somebody who is excited about being stimulated by all of that, they’re creative, experienced, curious, and keen to be leading with us and beside us in this area is going to be great.

We’ve talked about this before, balancing the current opportunities, needs, students, and parents who want to support projects in the here and now, then looking ahead to this exciting future for that matter that you’re talking about in regards to the Jericho land development. In many ways, as talked about before, you’re a school that’s done this before. You’ve built a school fundamentally from scratch. You’ve already got that foundation in place and not to be naïve. Not to be a Pollyanna. It’s going to take some work. It’s going to be a challenge, but it’s an exciting future that you’re able to create fundamentally.

It is, and finding the language, the graphics, the narratives, and the stories and what will be said in which meetings to have parents move past their concern. Their understandable concern of, “Is there going to be a large change? How might it impact or impact my child? We want to be a part of that. That’s exciting to create a legacy that’s going to last the next 100 years.”

It’s exciting to create a legacy that's going to last the next hundred years. Click To Tweet

Why Join West Point Grey

Is that the compelling reason for someone to come join you at West Point Grey? Why would someone want to perhaps leave where they are now, leave their organization and come join you? If we’re speaking directly to candidates.

There are the short-term, mid-term, and long-term rewards that we all experience in our careers. This is a wonderful place to work. It’s uplifting. It puts some wind in your sails every single day when you’re surrounded by these lovely, thoughtful, and remarkable people. We know work is important in the educational arena. Its impact is significant. It’s gratifying.

You get a chance to be a difference maker. All the way back to my original comments with the founding head to be in the summer of ‘96. What do you want to do? What do you want to create? Knowing that you’re not just a cog and a wheel of a large organization but you’re coming in and having a chance to affect change. That’s a compelling opportunity to shape the future. In fact, our mission statement is a beautiful succinct mission statement that I’m always proud to share with others. It’s quite simply, “Shaping lives of inquiry, action, and joy.” We’re curious about what’s in front of us, then we decide to take action and the joy follows naturally from that.

That’s great. I’m convinced. You outlined someone that’s experienced. Somebody that’s curious. Someone that’s creative. What other traits or background do you think we’re looking for in a director? What’s the background of the person you’d like to be working with in this role? You’re going to be called on a lot to do a lot of fundraising in the future. I hope you’re prepared for that. You’re going to be a close partner with this person. I know you’re doing it already.

Somebody who has the ability to both step in and step up and share their voice and say, “This is important. Here’s how we need to move this, lead me, help me, guide me, and support me in that work.” At the same time, be reflective and introspective enough and curious enough to understand or hear about the particular nuances and the complexities of the context that we’re currently in or historically why it is the way it is.

Somebody who is relational. Somebody who has a warmth and a social intelligence and can engage with and interact with others in all sorts of different arenas. We all have to shift depending on the meeting or the group that we’re working with at any particular time. Somebody who is determined and dedicated and goal-oriented about what needs to be accomplished by setting KPIs and working towards these goals in the year.

At the same time, there is a level of comfort with ambiguity and recognizing that sometimes there may be different influences that we’ll have to direct and form the decisions we make. If we have to shift or be flexible or take a left turn at some point, we’re good with that. We regroup and take off in a new exciting direction.

That’s a compelling case, Stephen. I’ve loved how you’ve phrased that and talked about the school here. Any final messages for potential candidates or curious people?

If you are indeed curious about this opportunity, we’d love to know that you’ve reached out and asked more about it. Maybe we have an opportunity to have them visit the school as well. When we have a passion for education and young people, that’s an important place for us to focus our energies. It’s a rare and compelling opportunity at this point to come alongside and lead a engaged group of staff, very keen parents, and excellent prospects to an exciting evolution. Seriously, once again now creating the next future for West Point Grey Academy. I can’t wait to see this happen.

I can’t wait either. I’m looking forward to introducing you to some wonderful candidates and making the magic, having the magic happen fundamentally. We do invite curiosity and questions. Anybody that’s interested or curious, feel free to reach out to me at [email protected] or check out the school’s web page. Have a look at our postings. Have a look at the brief and certainly welcome questions and interest.

Thank you again for your time and your excitement, Stephen. I’m compelled by the mission and vision that you have for the school. As you say, it’s a fantastic mission of shaping lives. I’m proud to be a part of it.

Thank you. I’m excited and looking forward to what comes next.

I appreciate it.


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