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Strategic Insight for Mission-Aligned Growth
Fresh Wind Consulting combines innovative thinking with practical experience to drive sustainable progress.
Our Pillars
Corporate Strategy
Community Impact
Strategic Partnerships
Diverse Sector Expertise
Impact: Driving Growth with Pace
Assess & Understand
  • Engagement and observation
  • Data collection and analysis
  • Internal relationship development
  • Initial insight report
Strategic Engagement
  • Prioritize opportunity areas
  • Strategic option map
  • Stakeholder feedback
  • High level strategy roadmap
Expansion & Revenue
  • Detailed strategic plan
  • Resourcing strategy
  • Reporting, performance and governance
Where We Lead & Serve
Strategic Roadmaps
Craft comprehensive, growth-oriented roadmaps tailored for scaling nonprofits and ambitious small businesses.
Organizational Transformation
Drive impactful organizational change, delivering measurable return on investment and sustainable growth.
Advanced IT Strategy
Align technology infrastructure with strategic objectives to fuel innovation and enterprise expansion.
Enterprise Risk & Security
Implement robust governance frameworks and advanced security protocols to ensure compliance and fortify digital assets.
Small Business Development
Accelerate market entry, optimize operations, and strategize for scalable growth within competitive landscapes.
C-suite & Board Advisory
Offer bespoke strategic counsel and board-level insights to empower executive decision-making and drive high-level initiatives.
About Our Founder, Leo Bailey
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.
Community Leadership
Board Trustee
Sick Kids Community Health: 2022-Present
Board Trustee
Black Urbanism Toronto: April 2025-Present
University Councillor
Queen's University: 2024-Present
VP Finance
Queens Black Alumni Chapter: 2021-2023
Program Mentor
Success With Age and Guidance: 2011-2022
Grant Review
YOF Grant Review Committee: 2019-2020
Work Experience
1
2011-2015
Infrastructure Consulting Analyst
Early Career Consulting
2
2015-2019
IT Risk & Governance Manager + Senior Manager, Digital Risk & Governance
Risk & Governance
3
2019-2023
Senior Manager, Risk Management + Diversity & Inclusion Director (C-Suite)
D&I Leadership
4
2023-2024
Director, Small Business Partnerships
Business Development
5
2024-Present
Founder & Consultant + Educator/Researcher
Academic & Consultant
Let's Work Together
Ready to Make a Difference?
Fresh Wind Consulting partners with mission-driven organizations and growing businesses ready to scale with intention. Whether you're navigating transformation, building sustainable operations, or positioning for growth.
Ready to explore how Fresh Wind Consulting can drive measurable impact for your organization?
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