Fractional COOs in Toronto Making Things Happen in 2025

Toronto Interim Chief Operating Officers to Know

Toronto doesn’t just build startups—it builds systems.

It’s a city where public meets private, where the startup ecosystem is growing alongside government programs, universities, and a rising impact economy. But for all its innovation, hiring executive talent in Toronto has always come with nuance. Salaries are high, full-time expectations are even higher, and for small but scaling orgs—especially in education, health, and nonprofit sectors—hiring a full-time Chief Operating Officer (COO) can feel like a stretch.

That’s why in 2025, more Toronto-based companies are turning to fractional COOs than ever before.

And we’re here for it.

At Digital Reference, we believe in cutting through the noise of titles, resumes, and glossy bios to uncover the real operators—the ones doing the work, building the systems, and helping teams scale with clarity. This list is our latest curation: a group of Toronto-based fractional COOs who are showing up and making things happen.

How We Built This List

We’ve talked to founders, reviewed portfolios, stalked LinkedIn timelines, and looked for more than just buzzwords.

To be included here, a fractional COO must:

• Be based in or work primarily in Toronto and the GTA
  
  
• Be actively engaged in fractional, interim, or embedded operational leadership
  
  
• Have experience working with early to mid-stage orgs, especially in education, tech, and social impact
  
  
• Align with our values of Radical Authenticity and Radical Transparency
  
  

This isn’t a list of execs who used to run ops 10 years ago. It’s a list of people doing the work right now.

(If you want to learn more about how we vet operators, check out: Replacing the Resume and What Is Radical Transparency?)

Let’s get into it.

The Fractional COOs Making It Happen in Toronto

Nana Obeng

Founder, HIGHPOINT Consulting

Nana Obeng is one of Toronto’s most trusted names in operational transformation. Through HIGHPOINT Consulting, she helps women-led organizations get clear on what’s working, what’s not, and how to move forward with purpose. Her experience spans regulated industries, nonprofit, and startup ecosystems—making her a rare operator who can work across sectors without losing traction.

Why choose Nana:

• Deep experience in change management and systems leadership
  
• Trusted by founders and CEOs to lead with clarity, urgency, and strong execution
• Strategic thinker with a clear tactical edge

The Digital Reference Team had the opportunity to connect with Nana 1on1 to ask a few questions about her fractional approach. Here's what we learned:

Nana, What's your typical approach to client engagements?

"My process starts with a detailed intake form completed by the CEO, Founder, or Owner, covering areas like team structure, business model, finances, and current challenges. I review it, then we go through it together to get a clear understanding of what’s really happening inside the business.From there, I build a focused plan aligned with the company’s goals and highlight what needs to be stabilized, improved, or restructured to support growth. My style is direct and honest; I surface what’s holding the business back and provide practical, actionable solutions.Once we’re aligned, we agree on how we’ll work together. I typically lead execution with the internal team, while keeping the CEO or Founder updated through structured, routine check-ins.Progress is measured using key metrics and milestones for full visibility into what’s working, what’s changing, and what’s coming next."

What type of clients are the best fit for you?

"The best-fit clients are Founders, CEOs, or Owners of women-led businesses generating $1M–$10M in annual revenue, often with small but growing teams. They’ve proven their offer, have strong traction, and are planning for growth - whether that’s expanding into new markets, launching new revenue streams, or preparing the business for sale or succession.They’re experts in their field, deeply passionate about what they do - but operations aren’t their strength. They’re overwhelmed by growing complexity, stuck in day-to-day execution, and know they need strategic support to scale or just stabilize the business.They’re ready for someone who can lead, integrate, and stabilize the business behind the scenes."

What are your specialties or professional superpowers?

"My specialties lie in supporting women-led businesses - particularly in health, wellness, and consumer products. I have deep experience in regulated industries and service-based models, from therapy practices to physical products for women.As a former engineer and co-founder of a CPG brand, I bring firsthand experience building and scaling from the ground up. Paired with my work as an operations professional, this gives me a unique edge: I don’t just understand strategy - I’ve lived the execution. I help businesses uncover what’s not working, build systems that support growth, and lead teams through change with structure and clarity."

What else should your clients know about you?

"I bring high energy and a strong sense of focus to every engagement. I’m driven by results and not afraid to push when needed but I believe the work should feel collaborative, energizing, and even fun. I value real partnership with business owners and thrive when we’re aligned, working together toward clear goals with mutual trust and momentum."

Nana, what motivates you professionally? What's your personality type? - Share anything that you believe gives prospective clients more information about the soft skills you bring to the table.

"In addition to being high-energy and results-driven, I’m a natural relationship builder known for creating trusted, judgment-free partnerships. I bring a grounded, collaborative presence-able to lead decisively while staying deeply attuned to the needs of the business and owner/founder/CEO. I’m motivated by helping founders regain clarity, feel in control, and - most importantly - feel hopeful and empowered as they see real progress. I value transparency, ownership, and momentum, and I thrive in partnerships built on trust and shared goals."

Jennifer Mitchell

Jennifer is a Toronto-based operator who focuses on sustainable scaling. She’s particularly effective in orgs where the leadership team is feeling stretched and systems are starting to fray. Her approach is thoughtful, people-centered, and grounded in real-world ops experience.

Why choose Jennifer:

• Great for orgs at the “almost breaking” phase of growth
  
• Strong background in operations and organizational behavior
  
• Known for building systems that scale and support teams

Karan Ramchandani

Founder, Your CxO

At Your CxO, Karan Ramchandani works with scaling startups and legacy organizations undergoing transformation. He blends strategic thinking with hands-on delivery, offering fractional leadership in areas ranging from operations and product delivery to revenue strategy. Karan is particularly effective in B2B and services-oriented orgs where process needs to meet performance. Your CxO helps pre-seed & seed startups to build there Fractional C-suite Leadership Teams & Fundraising as a Service.

Karan Ramchandani is a seasoned business leader, investor, and Fractional C-Suite consultant with over 15 years of experience driving growth for startups from ideation to Series X. As the Founder and CEO of Your CxO Online, Karan has empowered 10,000+ startups with strategic leadership, operational excellence, and fundraising solutions.

His expertise spans revenue growth, market expansion, and building scalable operations.Previously, Karan held leadership roles at Builder.ai, contributing to its global expansion and achieving significant revenue milestones. Now, he’s launching the world’s first C-SaaS AI platform, offering on-demand C-Suite leadership to accelerate startup success. Whether leading fundraising rounds, forming strategic partnerships, or driving operational transformation, Karan’s hands-on leadership makes him a trusted partner for founders navigating complex growth challenges.

Why choose Karan & Your CxO:

• You're a  pre-seed or seed startup in need of operational support
• Broad experience across startup and enterprise environments
  
• Offers tailored engagement models based on business stage
  
• Combines operational and strategic leadership in one package
  

Beau Scott

Founder, Forgexity

Beau Scott’s firm, Forgexity, focuses on forging clarity from operational mess. Whether it’s workflow redesign, internal team alignment, or building a strong rhythm for scale, Beau’s approach is structured, strategic, and very human. He’s a favorite among mid-stage teams looking to get serious about systems without going corporate.

Why choose Beau:

• Great fit for creative and product-focused teams
  
• Emphasizes operational empathy alongside performance
  
• Strong coaching and team-building approach
  
  

Michael DiPasquale

Founder, Simply Solutions

Michael DiPasquale built Simply Solutions to be exactly what it sounds like: an answer to operational complexity. He offers fractional COO support to organizations that need better systems, cleaner execution, and founder-level calm in the chaos. With a strong focus on small businesses and community-based orgs, Michael brings both empathy and edge.

Why choose Michael:

• Ideal for founder-led teams stuck in reactive mode
  
• Known for simplifying complex systems into repeatable workflows
  
• A trusted voice in education-tech and nonprofit spaces
  

Stephanie Allen

Stephanie Allen is a fractional COO with deep roots in education and youth-serving orgs. She’s known for her thoughtful approach to leadership transitions, ops overhauls, and org-wide transformation. Based in Toronto with strong ties to the nonprofit sector, Stephanie brings both a strategic mind and a social impact heart.

Why choose Stephanie:

• Expert in mission-driven ops and education systems
  
• Supports orgs during growth, restructuring, or leadership change
  
• Trusted interim leader for schools and social impact ventures
  

Tara Stubensey

Tara is the kind of COO who can walk into a startup, diagnose what's not working, and rebuild the engine while it's still running. With a background in both tech and education, she thrives in ambiguous environments that require fast execution and thoughtful systems thinking.

Why choose Tara:

• Specializes in scaling systems for small, scrappy teams
  
  
• Known for calm execution in high-stakes growth moments
  
  
• Strong operational lens with a product-first mindset
  

Alia Lachana

Alia is a dynamic operations leader who brings equity-centered systems thinking to her work. She’s passionate about designing processes that don’t just function well—but feel right to the people working within them. She works with both startups and nonprofits, especially those navigating hybrid and remote models.

Why choose Alia:

• Strong focus on equity-informed operations
  
  
• Great for teams rethinking team norms and internal culture
  
  
• Trusted fractional leader in education and workforce development spaces
  

Kevin Lau

Kevin Lau is an operations and strategy expert who thrives in fast-moving, high-growth environments. With a background that spans venture-backed tech and organizational design, Kevin helps orgs set up the kind of internal systems that scale without slowing down.

Why choose Kevin:

• Ideal for Series A–C orgs needing to build operating discipline
  
  
• Brings a data-driven approach to process improvement
  
  
• Known for helping founders transition from doers to leaders
  

Suzanne Dixon

Suzanne is a powerhouse when it comes to operational turnarounds. She’s often brought in during moments of transformation, leadership gaps, or major growth transitions. Her strength lies in quickly assessing the landscape and putting structure where it’s needed—without creating bureaucracy.

Why choose Suzanne:

• Strong record of leading during transitions and crises
  
  
• Known for level-headed leadership and people-first ops
  
  
• Especially strong in education management and nonprofit operations
  

Barbara Hopper

Barbara has decades of leadership experience and brings a systems + storytelling approach to her ops work. She’s great with stakeholder management, internal communications, and aligning operations with mission—especially in impact-driven orgs.

Why choose Barbara:

• Fluent in internal alignment and team communication
  
  
• Great fit for mission-first orgs and educational institutions
  
  
• Brings executive presence without ego
  

Donn Whitehall

Donn brings a structured, no-nonsense approach to scaling operations. He specializes in financial operations, systems integration, and strategic planning—and he's especially valuable to teams who are feeling the strain of rapid scale.

Why choose Donn:

• Deep experience in finance-backed operational strategy
  
  
• Great fit for companies at inflection points
  
  
• Calm, clear, and always execution-ready
  

Michelina DiNunno

Michelina is a trusted operational partner for startups and nonprofits looking to go from scattered to streamlined. With a background in HR, systems design, and operations leadership, she’s particularly good at aligning people and process.

Why choose Michelina:

• Expert in integrating people ops with execution systems
  
  
• Trusted by small orgs that need high-impact fractional support
  
  
• A strong cultural steward and operational coach
  

Kate Rootman

Kate specializes in growth operations—especially for startups entering the scaling phase. She’s known for her systems thinking, operational empathy, and ability to create flow between departments that don’t always communicate well.

Why choose Kate:

• Excellent at breaking silos and creating team-wide rhythm
  
  
• Great fit for orgs navigating scale without internal ops leads
  
  
• Strong coaching mindset with execution chops
  

Teodora Smith

Teodora is a strategic operator with a background in both corporate and social impact sectors. She’s an excellent choice for organizations that need to connect strategy with process and execute on complex initiatives.

Why choose Teodora:

• Ideal for orgs juggling multiple stakeholders or programs
  
  
• Known for building operational frameworks from scratch
  
  
• Strategic thinker with deep delivery experience
  

Toronto: A City That Demands Smart Ops

Whether it’s a school network in Scarborough, a nonprofit in Parkdale, or a fintech startup in Liberty Village, Toronto organizations face unique operational complexity. Hiring full-time leaders is expensive. Building internal systems is slow. And the talent market is crowded.

Fractional COOs are emerging as the bridge between today’s challenges and tomorrow’s scale—and this list represents some of the best in the game.

A Note from Digital Reference

At Digital Reference, we’re not here to sell you hype. We’re here to help you find the people doing the real work—especially the ones who aren’t shouting about it on LinkedIn. Whether you’re a founder, board member, or nonprofit leader, we’re building tools, lists, and insights to help you hire better, faster, and more honestly.

Want to know more about how fractional COOs work? Here’s a few more from Digital Reference:

• What to Look for When Hiring an fCOO
• Outsourced COO Services in Canada
• Replacing the Resume - Digital Reference’s Aspirational Target

And if you’ve got a name we missed—or you’re a fractional COO looking to be featured—reach out (hello@digitalreference.co). The list is just getting started.

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