What does it take to go from Project Coordinator to Executive Director in just 10 months?

In this episode of the Unfiltered Non-Profit Podcast, we sit down with Stephanie Crilly, Executive Director of the Economic Developers Council of Ontario (EDCO), to explore her remarkable leadership journey, the challenges of nonprofit management, and the systems that help a small team create a big impact.

Stephanie shares how years of experience prepared her for an unexpected leadership opportunity, what she learned stepping into an executive role, and how EDCO has successfully grown its membership, increased conference attendance, and built an engaged network of volunteers across Ontario.

We also discuss:

• Transitioning from staff member to Executive Director• Building strong relationships with your board of directors• Managing governance, strategy, and organizational growth• Leveraging volunteers to create a thriving nonprofit community• The power of mentorship programs and member engagement• Growing events from hundreds to nearly 600 attendees• How nonprofit leaders can avoid burnout and maintain work-life balance• Why family, boundaries, and mental health matter in leadership roles

One of the most fascinating parts of this conversation is Stephanie's insight into leading an organization with just two staff members while supporting an extensive network of committees, volunteers, mentorship programs, and professional development initiatives.

Whether you're an Executive Director, nonprofit CEO, board member, association leader, or someone aspiring to a leadership role, you'll walk away with practical lessons on leadership, governance, engagement, and sustainable growth.

🎧 Tune in to hear how the right opportunity, strong relationships, and a commitment to continuous learning can transform a career and an organization.

What does it take to lead a nonprofit through a global shutdown, a membership rollercoaster, and a $17 million investment in the future of an industry? 

In this episode of Unfiltered Nonprofit Podcast, Cherry Chan sits down with Joe Salemi, Executive Director of Landscape Ontario, one of the largest and most influential trade associations in North America. With more than 2,600 member companies, a $7M+ operating budget, 35 staff, 10 regional chapters, and over 160 events each year, Joe shares what it takes to lead a complex organization while keeping people, purpose, and strategy at the center. 

When membership surged by nearly 1,000 companies during the pandemic, then later dropped significantly as market conditions changed, how did Landscape Ontario respond? Did they panic, cut staff, or pull back? Joe walks through the leadership decisions that helped the organization stay strong, find new revenue sources, and continue growing despite uncertainty. If your organization has ever faced fluctuating revenue, changing member needs, or pressure from your board, you'll relate to this conversation. 

You'll also hear the story behind one of the boldest projects in the sector: a $17 million workforce training centre that is set to transform landscape and horticulture education in Ontario. What gives a nonprofit leader the confidence to place a bet that big? And how do you balance long-term vision with day-to-day operations? 

This episode is packed with practical insights on succession planning, revenue diversification, leadership development, event strategy, and leading through change. If you're an association or nonprofit leader thinking about growth, sustainability, or what the future could look like for your organization, this is one you'll want to watch all the way through. 

"What would you do if 30% of your organization's revenue disappeared?"

That was not a hypothetical question for Christine Nielsen, CEO of the Canadian Society for Medical Laboratory Science (CSMLS). In her conversation with Cherry Chan, she shares what it's like to lead an association through the loss of a major revenue stream that had been part of the organization for decades. The surprising part? Christine isn't panicking. In fact, she's remarkably optimistic about what comes next.

Cherry and Christine talk about the realities of nonprofit leadership when the path forward isn't entirely clear. How do you prepare your board for a major shift before it happens? How do you help staff navigate uncertainty? And how do you keep moving forward when you're grieving a loss while also trying to lead through it? Christine is refreshingly honest about feeling betrayed when the decision was first made, but she also shares why dwelling there wasn't an option. The conversation also explores board governance, long-term planning, and the challenge of working with a constantly changing group of volunteer leaders. Christine jokes that after 16 years as CEO she's had 16 different bosses, and if you've ever worked with a board, you'll appreciate her perspective on onboarding, governance, and setting everyone up for success before problems arise.

What really stood out to us was Christine's belief that change doesn't have to be a crisis. Sometimes it's an opportunity to refocus on what members truly need. As she puts it, CSMLS is currently in "containment mode," but fully expects to move into "flourish mode." It's a conversation about resilience, leadership, and finding opportunity in the middle of uncertainty, something every nonprofit and association leader can relate to.

This episode might leave you wondering: if your organization had to reinvent 30% of its business model tomorrow, would you be ready? And what investments should you be making today to prepare for the changes you can't yet see coming?

With AI shaping how we work, many nonprofit leaders are asking: what does this mean for the future?

At the OTUS Nonprofit Exchange, Cherry Chan shared a grounded perspective—starting with a simple but powerful question from her 12-year-old daughter: “If AI is doing all of this… what am I going to do?”

Her answer? We don’t have all the answers—but AI isn’t here to replace us. It’s here to change how we work.

From automating repetitive tasks to supporting proposals and communications, AI is expanding what teams can do—not replacing them. At OTUS, team members are already experimenting with AI tools to increase capacity.

But the real value of human work remains in three areas AI can’t replace: judgment, storytelling, and relationships.

In a time of uncertainty, Cherry’s message is clear: we’re not behind, and we’re not being replaced. The organizations that thrive won’t be the most technological—they’ll be the most human.

In this episode of the Unfiltered Nonprofit Podcast, Cherry Chan sits down with Lana Hann, Executive Director of Gilda's Club Simcoe Muskoka, for a deeply personal conversation about leadership, resilience, and what it really means to support the people behind a mission-driven organization. 

Lana shares the experiences that shaped her career in the nonprofit sector — from losing someone close to suicide early in life, to caring for her mother through breast cancer, to eventually facing her own cancer diagnosis years later. Throughout the conversation, she reflects on how those experiences changed the way she views leadership, workplace culture, and community support. Rather than separating personal experiences from professional work, Lana explains how those moments became the foundation for the kind of leader she wanted to become. 

Cherry and Lana also explore the operational side of nonprofit leadership and the realities many Executive Directors face every day. From balancing limited resources and growing programs, to building strong teams and creating psychological safety in the workplace, the conversation offers an honest look at the challenges of nonprofit operations. Lana shares practical leadership lessons around hiring, accountability, staff check-ins, and building a culture where everyone is willing to “roll up their sleeves” to support the mission. She also discusses how Gilda’s Club has expanded its services by collaborating with hospitals, facilitators, and community partners instead of duplicating existing supports — allowing the organization to better serve people impacted by cancer while remaining financially sustainable. 

At the heart of the episode is a conversation about people. About creating spaces where individuals feel seen, understood, and supported during some of the hardest moments of their lives. Lana shares the story behind Gilda’s Club Simcoe Muskoka, the importance of kindness in leadership, and why supporting staff as people first ultimately strengthens organizations as a whole. It’s an honest and thoughtful conversation that many nonprofit leaders — especially those carrying both personal and professional responsibilities — will relate to. 

$30 million raised—and Krystal Valencia still says fundraising isn’t the answer. 

Krystal is the founder and CEO of Rental Rescue, a nonprofit that steps in when affordable rental buildings are at risk of being lost. Instead of starting with grants or campaigns, Rental Rescue started with financial modeling during COVID—nights and weekends spent learning capital stacks, understanding cash flow, and figuring out how housing actually works as an asset. 

Over several years, that approach led to more than $30 million raised. But Krystal is clear: traditional nonprofit funding models aren’t built for problems at this scale. 

Foundations may hold massive endowments, but most distribute only around 5% of their assets each year. That means nonprofits are competing for a shrinking pool of capital while being asked to solve billion‑dollar housing challenges. In housing, the math breaks down fast. 

Rental Rescue flipped the question. Instead of asking “how much can we fundraise?”, they ask “what’s the minimum capital needed to make this sustainable?” From there, they build cash‑flowing structures, partner with credit unions, and put operational and digital systems in place so nonprofits aren’t handed buildings they don’t have the capacity to run. 

Fundraising still matters—but Krystal argues it can’t be the whole plan. Sustainability has to be designed, not hoped for. 

If nonprofits are expected to solve systemic problems, why are so many still built on short‑term nonprofit funding? 

In this episode of the Unfiltered Nonprofit Podcast, Cherry sits down with Melissa Ray, Co-Founder and Chief Operating Officer of Concord in the City Community Ability Initiative. Melissa shares how the organization supports adults with developmental disabilities through programs focused on independence, life skills, job skills, and community connection. She also explains the gap many families face once adults age out of school at 21 years old and why services like theirs matter so much.  

Melissa also gives a real look at what sustainable nonprofit revenue can look like in practice. One standout example is Concord in the City's coffee truck, which serves 300 to 400 customers every Saturday at the Brampton farmers market. It is not just a revenue stream. It is also a hands-on opportunity for people with disabilities to build confidence, develop job skills, and connect directly with the community.  

A big part of the conversation focuses on affordability for families. Melissa shares that Concord in the City has not raised membership fees since 2021, even as costs continue to rise. She explains that even a small increase of $10 a day would add up to roughly $100 more a month or $1,000 more a year for families, which is why the organization works so hard to grow fundraising, donations, and other community-based revenue instead.  

This episode is a strong reminder that nonprofits do not have to rely on one funding source to stay sustainable. Melissa shares practical examples of how Concord in the City is building a model that protects families, creates meaningful opportunities, and keeps the mission at the centre of every decision. 

• Melissa Ray on LinkedIn — Melissa Ray, Concord in the City Community Ability Initiative
• Concord in the City on LinkedIn — Concord in the City
• Instagram — @concordinthecity
• Instagram — @concordcoffeeonthego
• Facebook — Concord in the City
• Website — concordinthecity.ca

What actually makes fundraising work? 

Is it hiring one strong fundraiser? 
Is it a better gala? 
Is it sending more emails? 

In this episode of The Unfiltered Nonprofit Podcast, Cherry sits down with Sam Laprade, a fundraising leader with 30 years of experience helping charities strengthen fundraising, build better systems, and hire the right talent. 

This conversation is full of practical insight, but one message comes through loud and clear: fundraising is not a one-person job. 

Sam explains that a fundraiser cannot succeed without the right setup behind them. Passion alone is not enough. Successful fundraising requires strong systems, leadership support, board involvement, and a clear plan that the entire organization understands. 

Throughout the conversation, Sam shares where nonprofits often struggle. Many organizations hire a fundraiser but do not give them the foundation they need to succeed. Fundraising works best when the entire organization supports it — from leadership setting the tone, to board members opening doors, to strong internal systems like donor management tools and timely receipting. 

Another theme that comes up is how organizations focus their energy. Too many nonprofits pour resources into events while overlooking longer-term fundraising strategies like major gifts, monthly giving, and legacy giving. Those strategies take time to build, but they are often what create stability over the long run. 

Sam also brings a strong analytical perspective to fundraising. Her team analyzes donor data to help organizations better understand their supporters and identify patterns that influence future fundraising success. In many cases, that insight can be generated quickly, sometimes within 72 to 96 hours, by examining donor behavior and trends. 

Her work in recruitment also reveals how much demand there is for the right fundraising leadership. Since 2020, Sam has helped place 48 fundraising professionals, helping nonprofits find people who are the right fit for their culture, leadership team, and fundraising goals. 

One of the most practical moments in the conversation is when Sam explains the five pieces nonprofits need working together for fundraising to truly succeed: a strong strategic plan, a clear case for support, a fundraising plan, a stewardship plan, and a communications plan. When those five pieces align, organizations create a system where fundraising can actually grow. 

One of the strongest takeaways from the conversation is the tension many nonprofits face every day. Leaders are trying to deliver programs now while also building the revenue needed for the future. 

How do you keep delivering today while still investing in tomorrow? 

And what happens when no one is thinking beyond the next campaign? 

This episode is a thoughtful listen for nonprofit leaders who want to move fundraising from reactive to strategic, and build something more sustainable over the long term. 

In this episode of The Unfiltered Nonprofit Podcast, Cherry sits down with Adam Joiner, CEO of the Boys and Girls Club of Ottawa—an organization with 100 years of history and a big mission: creating safe, supportive spaces where kids and youth can grow into who they want to be. 

Adam's story is the kind you don't hear every day. He first walked into the Club at nine years old, nervous and unsure if he belonged. A staff member invited him to play ball hockey, and that small moment changed everything. What started as 40 minutes at the Club became a second home—and eventually, a career where Adam worked his way through multiple roles and locations before becoming Executive Director in May 2020, right in the middle of the pandemic. 

The conversation gets real about what nonprofit leadership actually looks like: 

• carrying the weight of responsibility 

• caring deeply while knowing you can't do everything 

• and trying to build something sustainable in a world where needs keep rising 

Adam shares a key reality: about 90% of their program funding comes from fundraising. That means the Club's ability to serve more kids often comes down to one thing—revenue. He also talks about a tough decision the organization faced in 2023, when inflation and rising costs forced a 25% service cut, including closing a location and reducing staffing. 

But this isn't just a story about cuts—it's also about rebuilding. Adam explains how they're growing sustainability through social enterprise, including renting Club and camp spaces to offset costs. Today, that revenue helps offset about $1 million in expenses, with a goal to increase that over time so they can serve more kids. 

This episode is a strong listen for anyone leading a nonprofit who's trying to balance mission, money, and the long game—without losing heart.

In this episode of the Unfiltered Nonprofit Podcast, we're joined by Deepa Chaudhary, founder of Grant Orb AI, to talk about what really drives grant success — and why so many nonprofit leaders feel stuck in an endless cycle of funding pressure. 

Deepa brings a rare perspective to the conversation. She's worked on both sides of the grant table: writing applications inside nonprofits under real operational pressure, and reviewing and awarding funding from the funder side. Her experience includes co-founding United Way Mumbai, raising funds for international organizations, and working with major foundations, corporate funders, and government agencies across Asia-Pacific. At one point, as a solo fundraiser, she wrote just six grant applications — and five were approved. 

That experience shaped how she thinks about grants today. Deepa explains that winning funding isn't about writing more grants — it's about alignment. Understanding who a funder is, what they care about, and how your work fits their priorities matters far more than polished language. She also emphasizes the long game: organizations that build real relationships with funders — beyond reports and deadlines — are far more likely to receive repeat funding. 

Grant Orb was born out of this reality. Deepa saw firsthand how grant work often falls to executive directors late at night, or doesn't happen at all because teams simply don't have the time or capacity. When new AI tools emerged, she saw an opportunity to apply them to one of the most time-consuming parts of nonprofit work. What once took 40–50 hours — researching opportunities, drafting applications, and tailoring responses — can now be done in minutes, starting from unpolished notes. 

Because Grant Orb is built by someone who has reviewed grants as a funder, the platform focuses on what actually matters: fit, clarity, and funder priorities. It helps nonprofits find aligned opportunities, strengthen weak sections, and avoid wasting time on grants that were never a good match in the first place. One example Deepa shares is a small Vancouver school that had never written a major grant before, but used the platform to apply for funding and secured $25,000 from the Canada Post Foundation. 

At its core, this episode is about access. Deepa's goal isn't to replace human judgment, but to level the playing field — so funding success depends less on time, staffing, or budget, and more on the strength of an organization's mission and ideas.