Best Fractional Chief of Staff Services in Canada

Canada Outsourced & Fractional Chief of Staff Agencies

At Digital Reference, we’ve seen an explosion of demand for high-performing fractional Chief of Staff (CoS) services especially in Canada. Startups, mid-market firms, and even large-scale enterprises are increasingly relying on outsourced, part-time, and virtual CoS providers to streamline operations, align leadership, and accelerate growth. But not all providers are created equal.

This article is a curated roundup of the most trusted, strategic, and founder-led Chief of Staff service providers in Canada. From those working shoulder-to-shoulder with PE-backed firms to those scaling SaaS growth from behind the scenes, these standouts are more than just extra hands; they're force multipliers.

Methodology: How We Curated This List of Fractional, Outsourced, & Virtual Chief of Staff Providers

We take our lists seriously. Every provider featured below met the following criteria:

• Research-Driven: We reviewed company websites, public bios, client testimonials, and case studies.
  
  
• Client-Reviewed: These providers have earned visible praise from clients on LinkedIn, Clutch, and in founder circles.
  
  
• Location-Based: This list features only Canada-based or Canada-operated fractional Chief of Staff service firms.
  
  
• Founder-Led: We prioritized firms with a named founder or CEO actively shaping delivery and methodology.
  
  

We aren’t ranking these providers; they're all excellent in their own unique lanes. Let’s get into the spotlights.

Canadian Fractional Chief of Staff Services 🔦 Provider Spotlights

Relumed

🔗 Website: https://relumed.com/

What they do:
Relumed helps founders and executive teams bring clarity, prioritization, and momentum through fractional Chief of Staff support and strategic planning services.

Who they work with:
Primarily tech companies, solo founders, and teams navigating post-Series A environments.

Operating model:
Virtual-first engagements with intentional prioritization sessions and executional roadmaps.

💡 Why they stand out:

• Emphasizes mental load reduction for founders Relumed literally “relumes” your energy and focus.
• Brings operational clarity through weekly sprint cycles and check-ins.
• Founder-built frameworks like the “Arc of Momentum” have become beloved by founder clients.
  

Marita Herkert-Oakland, Founder, Relumed

🔗 LinkedIn: https://www.linkedin.com/in/maritaherkert/

Marita Herkert-Oakland brings a unique mix of startup operations, design thinking, and CoS rigor. She’s known for helping founders clarify purpose, create scalable systems, and execute ruthlessly. Her leadership style blends encouragement with honest feedback making her a true behind-the-scenes accelerator.

Chiefly Consultants

🔗 Website: https://chieflyconsultants.com/

What they do:
Chiefly provides fractional executive support with an emphasis on Chief of Staff services, strategic planning, and internal communications alignment.

Who they work with:
Well-funded scaleups, PE-backed operators, and leadership teams in need of change facilitation.

Operating model:
Team-based consulting with access to strategic advisors, process designers, and operational leads.

💡 Why they stand out:

• Strong consulting pedigree translating high-level strategy into team-specific action.
• One of the few Canadian firms with deep communications specialization as part of their CoS stack.
• Known for “Founder Enablement” systems specifically built for hyper growth orgs.
  

Paul Carleton, Founder, Chiefly Consultants

🔗 LinkedIn: https://www.linkedin.com/in/paulcarleton/

Paul Carleton has held roles across communications, operations, and CEO advising a rare trifecta that shines in his work. He’s known for empowering leadership teams to align quickly, communicate better, and execute with confidence. His clients appreciate his calm presence and well-researched frameworks, especially in high-stakes transitions.

FlexPoint Consulting

🔗 Website: https://flexpointconsulting.com/

What they do:
FlexPoint Consulting offers fractional operations leadership, including Chief of Staff roles focused on business performance, OKR alignment, and org effectiveness.

Who they work with:
Canadian SMBs, scaling tech firms, and business unit heads in enterprise environments.

Operating model:
Outcomes-first consulting with metrics, KPIs, and accountability structures baked into every engagement.

💡 Why they stand out:

• Uses proprietary Performance Impact Frameworks to measure results.
• Has helped several firms hit funding, exit, or transformation milestones with CoS support.
• Deep experience with cross-functional leadership alignment.
  

Michael Daehne, Founder, FlexPoint Consulting

🔗 LinkedIn: https://www.linkedin.com/in/michaeldaehne/

Michael Daehne is a former management consultant turned operator, known for driving operational excellence through simplicity and focus. His clients describe him as someone who “builds alignment without adding meetings.” Michael’s CoS style is structured yet adaptable, with a sharp eye for metrics that matter.

Vannin Consulting

🔗 Website: https://www.vanninchiefofstaff.com/

What they do:
Vannin is a boutique fractional Chief of Staff consultancy exclusively focused on supporting purpose-driven leaders, especially women-led startups.

Who they work with:
Impact-oriented founders, small business owners, and values-driven exec teams across Canada.

Operating model:
Close-knit, high-trust engagements that blend strategic thinking with day-to-day execution.

💡 Why they stand out:

• Unapologetically focused on mission-aligned leadership.
• Works with founders on emotional resilience and business clarity.
• Creates Founder's Playbooks—documented operating systems for vision-led teams.
  

Keziah Wonstolen, Founder, Vannin Consulting

🔗 LinkedIn: https://www.linkedin.com/in/keziah-wonstolen/

Keziah Wonstolen is a rare mix of business strategist, operations lead, and personal development coach. With a background in leadership facilitation, she brings soul and structure to every engagement. Her clients praise her ability to see what others miss, making her a powerful ally in both personal and business transformation.

Tulloch Consulting

🔗 Website: http://www.tullochconsulting.ca

What they do:
Tulloch Consulting is a Canadian leadership advisory firm offering fractional HR, People & Talent operations, and CoS-level support. Their style is direct, people-first, and rich in startup and scaleup context.

Who they work with:
Often seen inside growth-stage tech firms, founder-led businesses, and mission-driven orgs.

Operating model:
Embedded partnerships with founders and CEOs hands-on, human-centric, and focused on organizational design, team dynamics, and executive decision support.

💡 Why they stand out:

• Integrates HR expertise with Chief of Staff functionality especially useful for founders without People leadership.
• Strong emphasis on leadership team alignment and cultural scaling.
• Trusted advisor to several remote-first companies across Canada.
  

Jana Tulloch, Founder, Tulloch Consulting

🔗 LinkedIn: linkedin.com/in/janatulloch

Jana Tulloch brings a deep background in strategic HR, organizational transformation, and executive operations. Her style is empathetic, proactive, and grounded in trust-building across leadership teams. Jana is known for her ability to bring clarity and structure to chaotic environments, a hallmark of modern CoS work. She’s also active in thought leadership on agile HR and workplace design.

Sidekick

🔗 Website: https://www.sidekickconsulting.ca/

What they do:
Sidekick offers fractional Chief of Staff, Business Operations, and Change Enablement services. They serve as operational partners, sounding boards, and action drivers.

Who they work with:
From Canadian tech founders to nonprofit executives and legacy business owners, Sidekick thrives in leadership transitions, scaling phases, and strategic pivots.

Operating model:
Flexible engagement models—from weekly execution support to strategic offsites and interim CoS roles.

💡 Why they stand out:

• Offers a clearly defined CoS-as-a-Service framework, honed over dozens of engagements.
• Distinct focus on change management and cross-team enablement.
• Seamlessly bridges vision with execution especially in complex org charts.
  

Bonny van Rest, Founder, Sidekick

🔗 LinkedIn: https://www.linkedin.com/in/bonnyvr/

Bonny van Rest is a strategic operator with a global background, having held senior roles across the Netherlands and Canada. She brings a systems-thinking approach to CoS work, combining process, empathy, and accountability. Known for her ability to simplify the complex, Bonny helps leaders cut through the noise and drive traction without burnout.

✨ Closing Thoughts from Digital Reference

At Digital Reference, we believe in radical authenticity and local-first discovery. This list wasn’t built by algorithms, it was built through deep research, real feedback, and a commitment to spotlighting Canada’s best CoS providers.

Whether you’re a startup CEO buried in decisions or a growing team in need of alignment, these fractional Chiefs of Staff can transform the way you operate. They’re not just support, they're strategic catalysts.

👉 If you're a fractional executive looking to be featured in a future guide, or a founder looking for a custom CoS match, reach out to us at Digital Reference.

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• Best Fractional & Part-time CFO Services in Canada

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