Canada’s charitable sector is in a period of concentration. The Fundraising Effectiveness Project’s Q4 2025 report found that while total dollars raised grew 5.0%, the donor base shrank for the fifth consecutive year (-3.6%). Between 2020 and 2025, donors giving $100 or less fell 17%; those giving $10,000 or more doubled. Revenue is holding up because major donors are giving more – but that makes the job of fundraising leadership more complex, not less.
The organizations best placed to weather what comes next are those with leaders who can deepen relationships at the top of the pyramid while rebuilding broader participation below it. A strong campaign result no longer tells you whether you have the right person for that job.
Relationships as Strategy
The FEP describes converting a first gift into a second as “the most consequential unsolved problem in the donor pipeline.” Overall retention edged up marginally (from 43.1% to 43.3%) in 2025, but new donor retention remained essentially flat. With the donor base already contracting, an organization that cannot convert first-time givers into ongoing supporters is eroding its pipeline with every campaign.
What separates strong fundraising leaders here is not charm or a gift for small talk – it is discipline. They treat stewardship with the same rigour as solicitation, and they build systems that sustain relational depth at scale, so that when a gift officer moves on, the donor relationship does not move with them. They know their major donors as people – what motivates them, what they value, what they worry about – and they have built a team that knows the same.
Commercial Fluency
The best development leaders think like revenue strategists – across the full portfolio, not just the current campaign. The CanadaHelps Giving Report 2026 highlights that monthly donors give 87% more on average than one-time givers, and that securities donations have grown 361% since 2020. A leader who cannot build sustainable program around recurring giving and planned gifts is leaving material revenue unrealized, and leaving the organization more exposed when campaign-by-campaign giving softens.
What this looks like in practice is a candidate who arrives at a board conversation not with a case for more fundraising spend, but with a clear-eyed analysis of where the current revenue mix is fragile and a specific plan for addressing it. That combination of diagnosis and proposal – grounded in both sector data and the organization’s own donor base – is rarer than it should be, and worth probing for directly in any senior search.
Leadership That Builds
Fundraising teams experience some of the highest turnover in the sector, and donor relationships are far more portable than most organizations realize. When a gift officer leaves, they frequently take years of relationship history with them – context that lives in their head, not a CRM. A leader who builds team stability and creates real development paths for their people is protecting one of the organization’s most valuable assets.
In our searches, the candidates who prove most effective over time are those who have built systems that outlast any individual’s tenure – who have surrounded themselves with people who complement rather than duplicate them, and who can articulate what their team learned under their leadership as clearly as what they personally achieved.
What to Look for in a Hiring Process
The qualities above are each findable in isolation. The difficulty – and the reason getting this hire right matters so much – is that they rarely travel together. A candidate can be a gifted relationship builder and a weak strategist. Another can think brilliantly about revenue mix but struggle to retain a team. The question is not whether a candidate has one of these qualities, but whether they have developed all of them under real pressure.
The questions that reveal this are rarely about results alone. Ask a candidate to walk you through a major gift relationship that stalled, and what they did. Ask what happened when a significant donor walked away, and how they managed it internally as well as externally. Ask how they have argued for long-term investment in development when short-term pressure pointed the other way. Ask what their best gift officer learned in their first year under them – and what they themselves learned most recently.
A candidate who has only operated in favourable conditions – growing donor base, strong economy, an established program they inherited – can look outstanding on paper and struggle when things shift. The candidates who answer those questions well tend to have built something from a difficult position, held a team together through a lean period, or turned a donor relationship around after it had gone cold. In a sector where the margin for error is narrowing, that kind of experience is worth more than a strong year in a good climate.
Bedford Group specializes in executive search for the Not-for-Profit sector across Canada and the US, placing fundraising leaders, Chief Development Officers, Executive Directors, and board members in mission-driven organizations. To learn more about how we support Not-for-Profits in finding exceptional talent, visit our Not-for-Profit practice page.