Transform your organization. Amplify your impact.
Schedule a Conversation
About the Founder
Bachelor of Commerce
MBA
PhD Candidate
Leo Bailey is a strategist 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, strengthen operations, and drive sustainable growth.
With experience across financial services, digital transformation, grassroots community leadership, and board governance, Leo blends strategic discipline with deep empathy for mission-driven work. This background equips Fresh Wind with a practical, people-centred approach to solving complex challenges.
Leo is also an educator and emerging academic, teaching entrepreneurship and small business management while pursuing research in digital inclusion and community-centred innovation. His commitment to servant leadership and community impact shapes Fresh Wind's philosophy and fuels the work we do.
Strategic Leadership
10+ Years
Educator & Researcher
Digital Inclusion & Innovation
Community Leader
Board Trustee & Advisor
Cross-Sector Experience
Finance, Nonprofits, Public Sector
What We Do
Fresh Wind Consulting is a founder-led advisory firm serving nonprofits, NGOs, public-sector organizations, community agencies, social enterprises, and small businesses.
Strategy & Organizational Transformation
Building clarity, alignment, and sustainable systems for growth.
  • Who this is for: Nonprofits, NGOs and social enterprises navigating growth
  • Key Deliverable: Strategic roadmap and action plan
  • Key Outcome: Organizational clarity and alignment
Leadership & Executive Coaching
Developing confident, capable leaders who drive meaningful change.
  • Who this is for: Executive directors, founders, and C-suite leaders
  • Key Deliverable: Personalized leadership development plan
  • Key Outcome: Enhanced leadership confidence and capacity
Research, Policy & Ecosystem Development
Creating evidence-based strategies and securing funding for impactful initiatives
  • Who this is for: Nonprofits, public agencies, and foundations
  • Key Deliverable: Grant proposals and funding strategies
  • Key Outcome: Secured funding and resources
Workshops, Training & Speaking
Building capacity through interactive learning and thought leadership
  • Who this is for: Organizations, conferences, and community groups
  • Key Deliverable: Customized workshop curriculum
  • Key Outcome: Enhanced team skills and capacity
The Fresh Wind Process
Five Steps to Impact
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
Let's Work Together
Ready to transform your organization and amplify your impact? Let's start a conversation
Insurance Policy # PSN0040225317
© 2026 Fresh Wind Consulting. All rights reserved.