Managing Director

About CSI The Centre for Social Innovation (CSI) is where changemakers gather to build a better world — one rooted in people, planet, and shared purpose. For 20 years, we’ve pioneered coworking, community bonds, radical hospitality, and social entrepreneurship, serving as home to nonprofits, social enterprises, artists, activists, philanthropists, and purpose-driven businesses alike.

Now, we’re evolving again — building the next generation of collaborative infrastructure for co‑creation, collective action, and lasting change. Housed inside Toronto’s vibrant Changemaker Club, CSI is becoming more than a place to work: it’s becoming the system, culture, and community that help people solve big problems together.

The Role - We’re looking for a Managing Director A strategic, operational, digitally‑savvy, and financially sharp leader who can turn bold ideas into working systems.

This isn’t a back‑office role. It’s a builder role. A number‑two with entrepreneurial instincts.

Someone who can toggle between a board meeting, a budget model, a digital dashboard, a facilitation session — and yes, even moving furniture for an event — and love all of it.

You’ll lead operations, finance, digital systems, data & AI integration, HR, and organizational culture — keeping the engine running while helping design the future: new revenue models, member offerings, constellations, and collaborative infrastructure.

You’re as comfortable exploring sponsorships and business development strategies as you are mapping workflows, setting up automations, or rethinking how digital tools can deepen connection and community.

Above all, you’re someone who brings rigour and heart — a systems thinker who believes hospitality and humanity belong at the centre of innovation. Bonus points if you’re also a “Zoholic” (that’s a Zoho Suite expert, in case you’re not now but want to be).

You Will… Build the Collaborative Infrastructure

Turn CSI’s strategic direction (CSI 2.0 / CIO) into operational reality.

Design systems that help members collaborate — summits, slack channels, shared services, digital platforms.

Support the emergence of “constellations” — member‑led collaborations tackling real issues.

Lead Operations & Financial Sustainability

Oversee finance, budgeting, forecasting, dashboards, and board reporting.

Understand real estate economics, community bond financing, grants, sponsorships, memberships, and earned revenue.

Build systems that make CSI more efficient, transparent, and sustainable.

Streamlining Existing & Revenue Development

Make it all easier and cleaner - for our members & the hospitality experience

Co‑design and launch new “products”: summits, membership tiers, services, ecosystems, digital offerings.

Test, iterate, and scale what works. Stop what doesn’t.

Culture, Team & People Systems

Create a culture of belonging, learning, joy, accountability, and initiative.

Oversee HR, hiring, onboarding, performance reviews, compensation design.

Support staff AND members — we are a community, not just a company.

Digital, Data & AI Strategy

Be unafraid of technology — champion smart, ethical adoption of tools (Zoho, AI, automation, data dashboards).

Question assumptions: What should we build, buy, automate, or stop doing altogether?

Ensure digital systems support human connection — not replace it.

Governance & Leadership Support

Work closely with the CEO on strategic planning, board reporting, budgets, philanthropy, and partner relations. Coordinate leadership team meetings, agendas, follow‑through.

Build trust & accountability across teams, board, members, and partners.

Hosting & Hospitality

Work with the CEO to shape the future of CSI’s hosting and hospitality services — designing the business models, space strategies, and member experiences that bring our mission to life.

Translate big‑picture vision into coherent hospitality ecosystems: building flow, amenities, pricing, programming, and the intangible “feel” of CSI spaces.

Guide the evolution of our spaces, F/B strategy, coworking environments, partnerships, and events through a lens of sustainability, accessibility, and community value.

Ensure our places are not just functional, but catalytic — platforms where collaboration, belonging, and social innovation thrive.

You Are… A builder, not just a manager — someone who gets things done, makes things work, and loves the messy middle between vision and execution.

10+ years of leadership experience, ideally across nonprofit, social enterprise, or purpose‑driven business.

Financially fluent — you can read a balance sheet, manage complex budgets, forecast cash flow, and speak confidently about financing, investment, philanthropy, and revenue models.

Digitally and operationally brilliant — comfortable with AI, data, and automation; adept with CRM, workflow, and finance tools; the kind of person who builds a system that actually works and teaches others to love it.

Entrepreneurial by instinct — a go‑getter who spots opportunity, acts quickly, and thrives in ambiguity.

A jack‑of‑all‑trades and master of momentum — equally at home designing a budget model, debugging a spreadsheet, facilitating a meeting, or moving chairs before an event.

Clever, curious, and funny — you take the work seriously, but not yourself.

Rooted in purpose — passionate about community, justice, climate, and collective action.

Why CSI? Because you believe hope is a strategy — and action is its proof. Because you thrive where imagination meets implementation. Because collaboration isn’t a buzzword to you — it’s how the world gets better.

At the Centre for Social Innovation, we’re building the infrastructure for hope — a home for people who care about people and planet, and who know that big change takes all of us. We’re a community of doers, dreamers, founders, and fixers co‑creating what’s next.

If you’re ready to roll up your sleeves and build the systems that make collaboration work, this is where you belong.

How to Apply Send your resume and a cover letter that tells us who you are, what you’ve built, and why this work matters to you. Applications will be reviewed on a rolling basis.

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