Guide.Partner.Impact
We help nonprofit and community leaders define what matters, build the right strategy, execute with systems that scale, and measure their impact.
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What We Do & How We Do It
Fresh Wind Consulting is a strategy-first advisory firm. We help leaders clarify direction, execute with focus, and measure what matters.
Strategic Advisory
Strategy, program design, growth and funding
Execution & Tracking
Dashboards, KPIs, impact reports, operating models
Targeted Delivery
Workshops, program support, short-term engagements
How We Partner With You
Fresh Wind offers flexible engagement models designed to meet you where you are and scale with your needs.
Support & Advisory
Short-term guidance and strategic counsel for specific challenges or decisions
  • Ideal for: Organizations seeking expert input on a defined issue
  • Engagement: Project-based or hourly consultation
Strategic Partner
Ongoing advisory support for leadership teams navigating growth or transition
  • Ideal for: Organizations building capacity and refining strategy
  • Engagement: Monthly or quarterly retainer
Transformational Support
Deep, hands-on partnership to drive organizational change and build sustainable systems
  • Ideal for: Organizations undergoing significant transformation
  • Engagement: 6-12 month intensive partnership
Comprehensive Advisory & Ecosystem Support
Full-spectrum strategic counsel, research, grant development, and ecosystem-building
  • Ideal for: Organizations seeking holistic, long-term partnership
  • Engagement: Annual retainer with multi-faceted support
How We Think About the Work
Our approach is grounded in a simple belief: clarity before execution, and strategy before activity.
Clarity Before Execution
We don't just do the work—we help you understand how to lead it.
Strategy First
We prioritize getting the direction right before building momentum.
Systems That Track Progress
We build systems that measure what matters and demonstrate real impact.
Tell Your Story Through Data
We help organizations communicate their outcomes to funders, boards, and communities.
Purpose-Driven Partnership
We partner with organizations creating meaningful change—and we're invested in your success.
About Leo Bailey
  • Bachelor of Commerce
  • MBA
  • PhD Candidate
Leo Bailey is a strategist, educator, and community-builder based in the Greater Toronto Area, and the founder of Fresh Wind Consulting. He helps nonprofits, small businesses, and public-sector organizations gain clarity, build practical strategy, and execute with systems that drive sustainable growth.
Leo brings experience from corporate strategy and consulting roles at organizations including Interac, RBC, and Accenture, alongside deep work across nonprofit, public, and private sectors. He is an instructor in the School of Management at George Brown College, teaching business and small business management courses—bringing real-world strategy into the classroom with strong student engagement.
His work is grounded in a commitment to equity, community impact, and economic empowerment—guided by a faith-driven purpose to serve organizations creating meaningful change. This shapes Fresh Wind's philosophy: clarity before execution, and strategy before activity.
Strategic Leadership
10+ Years Across Sectors
Educator & Researcher
George Brown College, School of Management
Community Leader
Board Trustee & Advisor
Cross-Sector Experience
Corporate, Nonprofit & Public Sector
Let's bring clarity to your next move.
Ready to define your strategy, execute with focus, and measure what matters? Let's start a conversation.
Engagements typically begin with strategic advisory before moving into execution and performance tracking.
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