Our Origin Story - Why I Started The Iron Sail Group

Our Origin Story – Founder’s Narrative

Nonprofit leaders and volunteer boards are stretched thin—spending too much time managing operations and not enough time advancing their mission. After more than 25 years supporting over 50 organizations across Canada, I founded The Iron Sail Group to change that.

Throughout my career—whether serving in a direct leadership role or as a strategic advisor—I saw how much time was consumed by backend tasks: tracking down invoices, updating outdated HR and volunteer policies, resolving IT issues, or preparing funding reports. These urgent but non-strategic responsibilities consistently pulled leaders away from the work that truly drives impact.

It became an inside joke among my fellow Executive Directors: we were always managing “all of the things,” but rarely had time to focus on the work that energized us or moved our organizations forward. The result was often reactive leadership, outdated policies, and burnout.

The Iron Sail Group was created to change that.

We specialize in helping third sector organizations manage the operational foundation—governance, finance, human and volunteer resources, IT, and recruitment—so leaders can focus on programming, fundraising, advocacy, and community impact. Whether through one-off projects or long-term retainers, we design custom and cost-effective support systems—delivered through our flexible fractional consulting model—that reduce risk, prevent stress, and build organizational resilience.

And we do it for a fraction of the cost most organizations are already spending. Many nonprofits invest thousands of dollars and countless hours trying to patch together internal systems and external support. We connect the dots—affordably and efficiently—so you can stop juggling tasks and start building capacity.

The result? More time, less stress, and a stronger foundation for impact.

My leadership philosophy is rooted in servant leadership—empowering teams to be their best through continuous learning, experimentation, and modeling the values we expect in our workplaces. I bring a project-based, consultative approach to every engagement, informed by my academic background and professional designations:

• Master of Administration and Master Certificate in HR Management and Labour Relations (University of Regina)
• Executive Certificate in Labour Management Relations (University of Saskatchewan)
• Bachelor of Arts in Political Science and Commerce (Saint Mary’s University)
• CPHR, SHRM-CP, RPR, CMP, RPT, and Prosci Certified in Change Management

I’ve led governance reviews, negotiated major partnerships, implemented IT transformations, and supported organizations through accreditation, restructuring, transition, change, and crisis response. I’ve also served in leadership roles across sport, culture, community services, and economic development organizations.

At The Iron Sail Group, we take a long-term partnership approach. Imagine starting your week knowing your payroll is processed, your IT issue from last week is resolved, and your HR policy is already updated to reflect new legislation. What could you focus on instead?

If you're a board preparing to hire your next great leader, or a CEO ready to reclaim your time and energy, let’s talk. We’ve been there—and we’re ready to help you get back to doing what you do best: delivering meaningful results for your community.

Reach out today to explore how The Iron Sail Group can become your next great partnership.

I look forward to hearing from you,

Craig

Craig Cherrett
Principal and Founder
The Iron Sail Group

‍