Fresh Wind Consulting Guide · Partner · Impact
Boutique Strategic Advisory  ·  Toronto, Canada

GUIDE.
PARTNER.
IMPACT.

Fresh Wind Consulting delivers impact with excellence and genuine community intelligence for the organizations doing the world’s most important work.

Engagements typically begin with strategic advisory.

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Organizations we’ve supported
The Salvation Army Black Entrepreneurship Alliance FACE — Federation of African Canadian Economics Black Entrepreneurship Knowledge Hub United Way Greater Toronto BC Community Alliance
What We Do

Three disciplines.
One firm.

Every engagement draws from the same methodology: clarity first, strategy before activity, and systems that make progress visible.

📋

Strategic Advisory

Facilitation and planning that produce a real roadmap — one your board can fund, your team can execute on, and your community can see themselves in.

  • Strategic plan facilitation & refresh
  • Environmental scanning & PEST analysis
  • Board & stakeholder alignment
  • Program design & growth strategy
  • Grant strategy & funding frameworks
⚙️

Digital Transformation

Practical modernization that serves the mission — dashboards, automation, and reporting infrastructure designed around how your team actually works.

  • Digital strategy & transformation roadmaps
  • Microsoft 365 & workflow automation
  • Impact dashboards & KPI frameworks
  • Operating model & systems design
  • Data governance & reporting
🤝

Social Impact & Capacity Building

Strategy and tools grounded in community intelligence — strengthening the internal capability that lets organizations deepen their impact and grow sustainably.

  • Social impact strategy & measurement
  • Organizational capacity building
  • Leadership coaching & facilitation
  • Workshops, toolkits & playbooks
  • Community & ecosystem partnerships
How We Partner

Engagement models built
around your reality

We meet organizations where they are — whether you need focused short-term guidance or a long-term strategic partner invested in lasting change.

Support & Advisory

Expert Counsel, On Demand

Targeted strategic guidance for a specific challenge, decision, or deliverable. Structured for speed and impact.

Ideal for: Organizations seeking expert input on a defined issue
Engagement: Project-based or hourly consultation
Transformational Support

Hands-On Partnership

Deep, intensive engagement to drive significant organizational change and build the systems, culture, and leadership that sustain it.

Ideal for: Organizations undergoing significant transformation
Engagement: 6–12 month intensive partnership
Comprehensive Advisory

Full-Spectrum Strategic Counsel

End-to-end partnership spanning strategy, research, grant development, and ecosystem-building for organizations seeking holistic, long-term impact.

Ideal for: Organizations seeking a long-term strategic ecosystem partner
Engagement: Annual retainer with multi-faceted support
Community-tier rates available for grassroots and emerging organizations. Budget should never be the barrier between a great mission and good strategy.
The Fresh Wind Edge

We’ve been in the boardroom.
We’ve never left the community.

Most consulting firms give you the playbook from one world. Fresh Wind gives you excellence in strategy and the intelligence of the community sector — because our founder has lived and led in both.

That’s why the organizations we work with don’t just get a strategy document — they get a partner who understands why the work matters, who it’s for, and what’s actually at stake if it stalls.

We bring clarity before execution, and strategy before activity — guided by a faith-driven commitment to serve organizations creating meaningful, lasting change.

Start a Conversation
15+
Years leading strategy, partnerships & community impact across financial services and community development
5
Canadian cities reached through the TD Propelling Black Entrepreneurship program
20+
National partnerships built and stewarded across sectors
Nationwide
A trusted network of social impact and community professionals across Canada and beyond
How We Think

Principles that guide
every engagement

Clarity Before Execution

We don’t just do the work — we help you understand how to lead it. Direction first, momentum second.

Strategy Before Activity

Busy is not the same as effective. We prioritize getting the direction right before building speed.

Systems That Track Progress

We build measurement frameworks that demonstrate real impact to funders, boards, and the communities you serve.

Tell Your Story Through Data

Your outcomes deserve to be communicated powerfully — to funders, stakeholders, and the public.

Purpose-Driven Partnership

We partner with organizations creating meaningful change and we are genuinely invested in your success.

Leo Anthony Bailey
Founder & Principal Consultant
About Leo Bailey

Strategist. Educator. Community Builder.

I grew up in Rexdale and Malton — two Toronto communities that taught me the power of showing up, and what’s possible when great strategy reaches the people doing the work on the ground.

After fifteen years leading strategy and partnerships at Interac, RBC, and Accenture, I founded Fresh Wind to bring that same caliber of thinking to the nonprofits and community organizations building a better world.

“Strategy isn’t a luxury. It’s a responsibility to the people your organization serves.”
Education
PhD Candidate · Carleton (Sprott)
Education
MBA · Queen’s University (Smith)
Education
BCom · Toronto Metropolitan University
Teaching
Instructor · George Brown College
Recognition
G. Raymond Chang Outstanding Volunteer, 2026
Recognition
Mississauga Outstanding Citizen Award, 2021
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Let’s connect

Ready to bring clarity
to your next move?

Define your strategy, execute with focus, and measure what matters. Let’s start with a conversation.

lbailey@freshwindconsulting.ca  ·  416-985-6573  ·  freshwindconsulting.ca

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