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Building and Leading a Fundraising Program with Jaime Wilson

By July 8th, 2023No Comments20 min read
Home » Building and Leading a Fundraising Program with Jaime Wilson

With years of experience in the not-for-profit sector, Coast to Coast Against Cancer Foundation’s Executive Director Jaime Wilson has developed a strategy on how to efficiently build a fundraising program and work hand in hand with others. As Jaime’s work provides hope for cancer patients, it also builds a database and aims to extend the organization’s reach. Jaime shares her experience working with True Patriot Love, as well as Coast to Coast Against Cancer, and talks about the strategies that have helped her initiate a successful fundraising program by working together as a team.

Listen to the podcast here:

Building and Leading a Fundraising Program with Jaime Wilson

We have Jaime Wilson, the Executive Director of Coast to Coast Against Cancer Foundation, a real leader in the sector and someone that we’re pleased to hear from. Welcome, Jaime.

Thank you.

You’re about a year into your role at Coast to Coast Against Cancer Foundation. I want to hear more about that, but first, tell us a little bit more about your background and what brought you to that role?

I started in the sector quite some time ago, about 13 years. I started at SickKids Foundation as an entry-level coordinator, which was a blessing. Here I am now thinking back and being able to learn some of the fundamental skill sets, especially by way of fundraising that I got to learn in such a big shop that does things quite well. From there, I worked at a couple of smaller niche shops and I found myself at Right To Play, which I believe when I reflect about my career and the things I’ve achieved is where I was tested. I say this to some of my junior staff, it was the experience where I was outside of my comfort zone every single day I showed up for a couple of years.

What kept you out of your comfort zone?

I was hired to come on board and develop a fund-raising program initiative. I put together a board, conceptualize, build the infrastructure, and essentially raise millions of dollars. I showed up my first day with a computer, a cell phone and that was about it. A lot of it was meeting as many folks as I could, I had a vision, I had a plan and the conversation went as such, “This is a great cause. These are the wonderful things we’re doing. This is my vision. Do you believe in it? Do you want to walk with me?” It was a bit of hope and faith every single day out talking to these people. Fundamentally, I believed in what Right To Play was trying to do of course. That drove all of these conversations and my energy and passion for what I was trying to achieve. It was hugely successful. What is now the Right To Play Champion’s Program, a group of philanthropists, senior-level executives, high net worth, ultra-high net worth individuals that come together and raise funds for Right To Play programs internationally.

In moments of frustration with communication and lack thereof, going back to the organization’s mission is essential. Click To Tweet

It was so successful in the Toronto area that they asked me to do the same in the New York office, which was a very exciting opportunity. I used the relationships in Toronto. Most of these folks had offices in Manhattan, New York. A lot of them were in the finance sector. I leveraged those relationships and contacts in Toronto to make connections in New York, did the same in New York and build the program up there. When I say out of my comfort zone, I didn’t show up with a task list or there was no one in my job prior to me. It was entrepreneurial. It was starting a business within a business. It was super exciting. Without that opportunity, I would not have realized how much I loved building, what my strengths were ultimately and my skill sets.

It’s something that happens quite a lot in the sector where you’ve got both the person in charge of fundraising, learning and the organization itself learning how to fundraise. How to be in order to be successful at fundraising. How much were you educating the organization as you were building these programs in both Toronto and in New York?

Quite a bit. Right To Play, before I showed up basically ran on government funding and most of the countries they fundraised in were different than the countries they had programs in. The national offices of which there were five were all fundraising offices, but mostly they dealt with government grants. The big one in Canada was the CIDA grant, the Canadian International Development Agency. That was most of the funding. That was part of the intention. It was to create funding outside of government funding. Thankfully, they had that foresight because shortly thereafter the funding stopped from CIDA, which is now something else I believe. They had a few folks that wrote proposals and knew how to report back to government agencies. Outside of that, in terms of relationship management, networking, engaging cultivation and peer to peer, developing those relationships was not something anyone, the vocabulary wasn’t even there. I was fortunate because I built my own team and branched out to help the corporate build their own team. Our Toronto national office went from maybe 4 people to 30.

Almost overnight, fundraising moves from being a nice to have to supplement government funding to the primary source of income for the organization. Did you get a better parking spot or a bigger office when that change happened?

We are a not for profit after all, but I did along with that. I’m blessed with the opportunity of traveling. I was in Africa a number of times to witness the programs. I climbed Kilimanjaro with some of my board members and some of our ambassadors, which was an outstanding experience. Near the end of my tenure there, I was in New York working part-time, 50% of the time in New York and 50% of the time in Toronto. I’m truly grateful for the opportunity I was afforded that I rightfully earned. I still don’t think many people ever would be extended opportunities that I have in the roles that I’ve done. I’m lucky.

You left Right To Play and joined the True Patriot Love Foundation. What was that transition like?

Similar to how I got to Right To Play, I was recruited. I had a headhunter that was pursuing me. She was tenacious. It was about a few years at Right To Play. The programs were doing well. I hadn’t thought about leaving, but she pursued me consistently for a few months. Finally, I said, “Fine, I’ll meet you for a coffee.” There was a little coffee shop in the base of my office building and I said, “You have fifteen minutes.” I wanted to get her off my back and what she had to talk to me about was intriguing. Recognizing what I loved about what I did in my role at Right To Play was building and that entrepreneurial spirit I was afforded. That was what True Patriot Love was looking for.

Their revenue was not from the government, but it was events. They have three events and that was all their revenue. Recognizing that they had to diversify, they were looking for somebody to build the revenue streams, build a fundraising team and development team essentially. Someone once said to me, “Always leave on a high note.” Although I wasn’t actively looking to leave, I could have potentially stayed there for several years at Right To Play. I saw the opportunity and it was another opportunity to create something of my own. That’s what I did. I went there as VP and I left as a Chief Development Officer. When I started there, our revenue was under $4 million and it had doubled when I left.

How long were you at True Patriot Love?

Four years.

Was it a similar transition from True Patriot Love to Coast to Coast?

It was, except it was a board member of Coast to Coast who I had met through someone I worked with at True Patriot Love, interestingly enough. We had hit it off and, he said to me, “Jaime, we will work together.” We had a couple of conversations and over the course of a couple of years we talked about Coast to Coast. At one point, I had met a lot of the board members and it fizzled a bit, which was fine. I never find myself in the position where I’m unhappy, I don’t want to jinx that. Time went on and I circled back and they circled back with me about Coast to Coast. It was a similar opportunity to True Patriot Love. “We have events and we want someone to lead the evolution of the organization.”

Sending letters and following up phone calls get people excited about change and fundraising in general. Click To Tweet

I took it and there was also a unique component of the Coast to Coast opportunity, which was merging with other organizations. Would it be one, would it be two or would it be a few? Which was intriguing to me looking at building my skill set, that was something I’d never experienced and saw the opportunity for some real personal and professional growth. I had a number of conversations with the chairman before accepting the role. Although our skill sets are opposite ends of the spectrum, I would say we shared the excitement and a similar vision for what we saw in terms of the future of the organization. The merger aspect, the chairman, and our alignment was a big reason why ultimately I accepted them.

You’ve taken over at an interesting time in the life of that organization. It is one of the known challenges in the sector to be the staff person that takes over after the founder, and that transition from the founder or the founding board to professional leadership can be challenging. How have you approached this at Coast to Coast?

To be honest, it has had some challenges. There are the sensitivities around letting go from a founder perspective. Fortunate enough for me, I had worked closely with the founder when I worked at Right To Play. I had worked with him on activating his network in the pipeline. I had regular calls with him almost daily. I was familiar with that backing off, but then swooping in. Some of those characteristics, they made a lot of sense to me and I’d seen them before, it wasn’t brand new. That was helpful for me in terms of managing up but I ultimately treat our founder as he’s one of our most valuable donors. Regardless of how engaged or not engaged he wants to be, ultimately, he drove the organization to achieve what it has now.

I respect that and fundamentally it comes down to mutual respect. The first few months it was a lot of gaining his trust, being communicative, being transparent, asking his advice, and I did that on a regular basis. Offering to meet up, have breakfast or chatting with him about my vision and getting him excited and on board was important. I saw the first board meeting, he was quite quiet. The second board meeting, I saw him getting engaged. The last board meeting, he was my biggest cheerleader. I’m not going to lie, which was great to hear. I don’t imagine the amount of passion, blood, sweat and tears that he’s put into getting this organization up and running. I imagine it would be hard to let go. I always keep that in the back of my mind. There are moments where I do feel frustrated maybe with the communication or lack thereof, but I always come back to the mission of the organization and that’s why we are all here.

It’s often set of professional staff going into organizations where the founder is exiting, it’s not the first executive director that builds the organization. It’s the one that follows that first one or the same analogy as the second mouse gets the cheese but it sounds like you’ve done a lot to build that relationship, to build that trust. By investing that time, you’ve turned the founder instead of an obstacle into a real asset. Maybe you could tell us a little bit about how Coast to Coast fits in the childhood cancer world, in Ontario, in Canada, and where you want it to fit as the organization continues to grow.

Coast to Coast was founded out of a grassroots cycling movement. It started with one cycling event, morphed into a few more cycling events and to the culmination of one cycling event that went across the country. That was quite spectacular. This all took place from 2003 to 2007 I would say. At that, which point, it became Coast to Coast Against Cancer. To date, the organization has dispersed over $50 million nationally to programs, whether it’s in hospital programs, quality of life programs, research for kids with cancer and their families. It was quite a grassroots shop. We’re working to professionalize and grow. It’s outstanding what the organization has achieved. In terms of where we collectively, my chairman, the board, and most of the staff at this point would like to see the organization grow, is to move outside of looking at and engaging the same demographic, the cyclist.

They’ve all been engaged. We’re finding that we need to look at different initiatives. We’re looking at diversifying the revenue we bring in and stabilizing our organization. We’re looking at being more of a proactive thought leader in the space. We’ve acquired a virtual organization. You could call it an advocacy organization that we’ve rolled up into Coast to Coast. We’re building that out and we’ll have an advocacy policy arm to the organization. We’re building out governance structures, doing a deep dive into who we grant money to, why, what does that mean in the landscape and the big picture, what does that mean in the next few years for example? Do you think it’s a way to invest more in research or more in quality of life programs? We built out a grant committee that is comprised of experts in the sector, along with patient families, along with cancer survivors to take a deep dive, look at that, and be more proactive about what we fund. Our donor can have the greatest impact possible.

I want to go back to something you said about professionalizing the organization. The professionalizing the organization, you’ve come in having built effective programs at two prominent and successful fundraising organizations. This is the first time in the executive director role and you come on the first day. What were the signs that you needed to do that professionalism, professionalizing of the organization and how did you start?

There were no processes to anything. People came and went as they pleased. The rules overlapped and intersected. People didn’t have clarity around what they were achieving, why and what it meant to the greater vision. There’s a lack of skill sets, lack of communication at large between colleagues. It was a grassroots organization. We essentially could be working in somebody’s garage. It was a bunch of friends that were like, “Let’s get this done.” There was this lack of forward thinking or strategic thinking.

That entrepreneurial grassroots energy that made the organization successful is important in the life of the organization. The move to professionalism represents unique challenges both for the people that had been there for a long time, but also for the donors who’ve been supporting the organization, I would imagine.

Change is hard, ultimately, for most people. You could compare it to managing the founder and building that relationship for success. It’s been similar to some of the staff. I came in and most of the staff had been there several years. They were friends of the founder or the founder’s wife. You’ve got a good sense that most folks weren’t there because they were qualified to be there, and that’s not discounting how hard they worked and their passion. There wasn’t that thinking around, “This is what we need to achieve. What is the team that’s going to get us there?” That’s been the most time-consuming aspect of what I do on a daily basis.

I personally love fundraisings. I’ve found in the first few months I was caught in the weeds of operations, managing staff, walking them through, and a lot of them don’t even understand the not for profit realm. It’s simple things like receipting, stewardship and sending a letter or a follow-up phone call. We weren’t doing those things. It’s back to basics. I spent a ton of my time coaching, empowering, and I’m getting people excited about change if that makes sense because I can’t do it all myself. That was the biggest challenge starting out. I went in there with expectations that I would inherit a team that understood how to drive things forward. Unfortunately, that wasn’t the case. Have they come a long way? Absolutely. Are they excited about all of the new initiatives we are up to this year? Absolutely. That’s a huge win for me.

Change is hard, ultimately, for most people. Click To Tweet

That is a significant turnaround in a short period of time. One of the things that I liked about your strategy going into the organization has been to engage the board. Make sure that the board was actively involved in not just the theory and the governance of the organization, but into the working of the organization and working to support the organization. It resonates with a lot of what we find here at the Discovery Group for boards that have directors that are actively helping with the fundraising or actively helping with some part of the core business tend to have aligned boards. You don’t hear the typical complaints from the directors of, “I don’t think the organization is making good use of my time.” Given what we’ve talked about. In other times, I know none of your directors are saying, “I don’t think they’re making good use of my time,” because you’ve made them busy. How have you gone about that?

I’ll start with saying that the board itself came together. They are all friends of my founder. It was my founder saying, “I have this vision, we all like to cycle. Let’s cycle in some events and raise some money.” Their board meetings took place when they did. I’m not talking out of school. This is admittedly what they tell me. They would have a board meeting impromptu. He would call the night before, “Let’s meet at the pub and talk about Coast to Coast.” If you can imagine, they were not engaged at all. They would attend events and wait for that evening phone call to have a meeting the next day type of things. Although all great individuals, they’d been around a while and we’re friends of the founder. Where I started in terms of the strategy was I met with each of them individually, whether it was for lunch or breakfast. The key was to make it less of a meeting style. I wanted them also to get to know me on a personal level. When I speak in person with somebody, you can tell my passion and excitement for things. I wanted to get that across. I feel like that’s infectious in a lot of ways. If I’m chatting with somebody who’s completely engaged and excited about something, I can’t help but want to be as well.

I started there and I did a lot of listening, tried to understand how they wanted to help, how much they wanted to be involved, what their skill sets were and what would capture their imagination. I didn’t want to take the approach where I was telling each one of them what they were doing. I wanted them to tell me ultimately. Within a month and a half, I had them coming forward and saying, “I can go out and help fundraise. I can go to meetings. I can make introductions. I will work on creative events.” My nature is I’m like a dog with a bone. If they offered to do something, they’re not going to hear the end of it. In a diplomatic and respectful way, but I don’t let them get away with not moving things forward. At the same time, I have emails in response, how excited they are for the year ahead, and they’re bringing forward initiatives that, “A friend is doing an event and they asked if we could be the charity of choice.” There are more things that are coming out of the woodwork. Left to their own devices, they’re going out and finding these opportunities. I keep them engaged. It comes down to communication first and foremost. Whether I send out updates on wins that we’re having or I try to get them on the phone every couple of weeks, even if it’s to status something or to give them an update on something we’re excited about at the organization. That goes a long way.

That familiarity with the change that’s happening in the organization and the consistent reminder of the mission of the organization heavily worked well to keep the board engaged. What are you looking forward to the organization as you look ahead as the executive director?

I’m looking forward to many things. A lot of the initiatives I’ve brought forward, a big one is an opportunity to work on some survivorship research and some of those big projects. I put together some big proposals first for a significant amount of money, $500,000 to $1 million for some survivorship research that would be partnered with the Canadian Institutes of Health Research and the Canadian Cancer Society. That’s a huge opportunity for us on many levels. The strategic partnership firmly plants our name into the psyche of those organizations. That’s an exciting thing that I’m working on personally. We’re also doing a gala with about 500 people.

We’re at a perfect time in the evolution of the organization because what I’ve noticed coming on board was we never talked about our impact. We don’t talk about our beneficiaries, the great work that we fund, and what that translates to in terms of outcomes and what that means. Our program for that evening is all about impact, our beneficiaries, and how we’re making a difference. It’s about time that we got to tell that story. Optically, from somebody on the outside before I came on board, it looks like an event organization that on side note donated money. It’s changing that narrative and helping externally and internally. We’re more focused on our mission and our mission-driven organizations.

Along with that, it’s a big cultivation piece. Only half of the people there will be loyal supporters that have been around since the beginning and the other half will be new people. It’s building our database and extending our reach. It ticks all the boxes for us and where we are. There are many more we’re doing cause marketing campaigns. We have a young professionals’ network that started in that are already rolling with things. They’re engaged and incredible. I’m excited to see the things that they’re going to do. We’re embarking on a big virtual campaign, which we’ve engaged some celebrity athletes that’ll lead that charge. There’s a lot of excitement.

That’s great and I can hear the excitement in your voice and also the awareness of how much work you have ahead of you. I want to touch on three things that I noticed that would be valuable for our readers. One is for people starting out in their career to look for positions that push them out of their comfort zone. To exist in a space that you haven’t been in before, you have to find yourself, learn yourself, and teach the organization that you’re working on how to be successful. The second and this is a valuable point, not just for this show, but something that needs to be out in the community. It’s the challenge of transitioning from a founder to professional management has been the rocky shores that wrecked a lot of boats over the years.

You’ve done such a great job of building that relationship through investing the time and getting the founder excited about what the future holds for the organization. It changed his perspective from worrying about whether letting go of his baby to now excited about where it’s going. That is a huge accomplishment. Finally, for an organization that wants to increase its impact and increase its dollars raised, you’ve done a great job of engaging the board where they are. Rather than coming in with a lot of policies, “Here’s how we’re going to change it,” you’ve invested the time with them as individuals and as a board to bring them along on the journey that you’re leading the organization. It’s been impressive to watch.

Thank you very much.

Thank you very much for being a part of the show. I look forward to watching Coast to Coast as it advances over the years.

That’s wonderful. Thank you.

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About Jaime Wilson

 Jaime is results-driven fundraising professional. She joins the Foundation from True Patriot Love Foundation where she was Chief Development Officer. Her prior experience includes senior roles with SickKids Foundation, Villa Charities Foundation and Right To Play.

Jaime is an inspiring leader who will bring strong leadership, vision, advocacy and program management skills to her new role with the Foundation. Jaime earned her undergraduate degree in English Literature from York University in Toronto.

Among her many notable accomplishments, she includes a summit of Mount Kilimanjaro, an expedition to the North Pole and sea-kayak journey through the Bay of Exploits, Newfoundland. She enjoys spending her free time with her 3-year-old son, Henry Maddox.