Best Fractional Chief Sales Officers in Toronto

Toronto Fractional CSO Services & Fractional Chief Sales Officers

Toronto has quietly become one of the most sophisticated revenue markets in North America. It’s a city shaped by enterprise buying behavior, cross-border go-to-market strategies, and a dense concentration of B2B, SaaS, financial services, and professional services organizations that sell into complex, highly informed audiences.

Revenue leadership in Toronto tends to be pragmatic rather than performative. Buyers expect credibility. Teams expect structure. Boards expect predictability. And founders—especially those scaling beyond Canada—need sales leadership that understands process, people, and pressure in equal measure.

That’s exactly why fractional Chief Sales Officers have become such a powerful part of the Toronto growth ecosystem. These leaders bring senior-level revenue experience without the long-term risk of a full-time executive hire, helping organizations professionalize sales motions, align teams, and scale responsibly.

At Digital Reference, we spend our time studying how senior operators actually show up in-market—how they lead teams, how they earn trust, and how they create clarity across revenue organizations. 

This guide highlights a curated group of Toronto-based fractional CSOs who reflect what strong revenue leadership really looks like in this market.

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🏒 Our Methodology: How Digital Reference Curated This List of Toronto’s Top Fractional Chief Sales Officers

This list was curated through hands-on research and qualitative evaluation, not automated lists or keyword scraping. Every professional featured here is based in or actively serving the Toronto market and met a clear set of criteria:

• Demonstrated ownership of sales or revenue outcomes
• Experience operating as a fractional or interim sales leader
• Clear positioning around go-to-market strategy and execution
• Evidence of credibility through leadership roles, frameworks, or advisory work
• A practical understanding of how revenue intersects with hiring, enablement, and performance

We reviewed LinkedIn profiles, firm websites, service descriptions, and public-facing thought leadership to understand how these leaders actually work with clients. Just as importantly, we looked at how they approach sales team structure, accountability, and leadership communication—areas where revenue strategy and people management overlap heavily.

This is not a ranked list. It’s a curated snapshot of Toronto-based fractional CSOs whose experience and approach align with how modern companies grow.

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🌟 Meet the Top Toronto Fractional Chief Sales Officers

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🍁 Brad Gilmour

Founder | Fractional Chief Sales Officer (CSO) at BAG Sales Excellence

Brad Gilmour has built his reputation around one core idea: sales scalability is a leadership discipline, not a personality trait. As the founder of BAG Sales Excellence, Brad works with growing organizations to install the structure, process, and leadership cadence required to move from founder-led selling to repeatable revenue performance.

Brad’s work as a fractional CSO often centers on companies that have proven demand but lack consistency. His approach is methodical—focused on diagnosing where deals stall, where accountability breaks down, and where sales teams need clearer expectations to perform.

What sets Brad apart in the Toronto market is his emphasis on sales maturity models. Rather than forcing premature scale, he helps leadership teams understand what “good” actually looks like at each growth stage—then builds toward it deliberately.

Key elements of Brad’s fractional leadership style include:

🔹 Designing scalable sales processes aligned to growth stage

🔹 Creating clarity around roles, metrics, and performance expectations

🔹 Supporting founders through the transition away from ad hoc selling

🔹 Building leadership rhythms that reinforce accountability

For Toronto companies aiming to scale revenue without chaos, Brad offers a grounded, systems-oriented approach that resonates with boards and operators alike.

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🍁 Jonathan Vassallo

Fractional Sales & Executive Leader at Junction Sales

Jonathan Vassallo brings a deeply execution-focused mindset to fractional sales leadership. Through Junction Sales, he partners with organizations that need senior sales direction but aren’t served by theory-heavy consulting or one-size-fits-all playbooks.

Jonathan’s background reflects hands-on leadership across sales strategy, team management, and execution. He works closely with leadership teams to identify what’s actually preventing growth—whether that’s unclear messaging, misaligned incentives, or sales teams operating without a consistent process.

In Toronto’s competitive B2B landscape, Jonathan is particularly effective with companies selling complex offerings into sophisticated buyers. His work often involves tightening qualification, improving pipeline hygiene, and ensuring sales teams are spending time on the right opportunities.

Jonathan’s approach is characterized by:

🔹 Clear prioritization of revenue-driving activities

🔹 Practical coaching for sales leaders and frontline reps

🔹 Alignment between executive expectations and sales reality

🔹 A bias toward action over abstraction

For organizations that want less talk and more traction, Jonathan offers fractional leadership rooted in real execution.

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🍁 Susie Halasz, CSL

Fractional VP of Sales at Sales Xceleration

Susie Halasz brings a blend of structured sales leadership and people-centric coaching to her work as a fractional VP of Sales with Sales Xceleration. Her background reflects years of experience leading sales teams and helping organizations implement repeatable systems that support both performance and culture.

Sales Xceleration’s model gives Susie access to proven frameworks and peer insight, but her impact comes from how she adapts those tools to each client’s reality. She works closely with leadership teams to establish sales infrastructure while also focusing on the human side of selling—communication, motivation, and development.

Susie is especially effective in environments where sales teams are growing or resetting expectations. Her leadership style emphasizes clarity, consistency, and trust—qualities that resonate strongly in Toronto’s relationship-driven business culture.

Highlights of Susie’s fractional leadership include:

🔹 Building structured sales processes without stifling autonomy

🔹 Coaching sales managers to lead with confidence and clarity

🔹 Aligning compensation, goals, and behavior

🔹 Strengthening collaboration between sales and other functions

For Toronto companies seeking balanced, credible sales leadership, Susie offers a steady hand and a proven approach.

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Why Fractional CSOs Work So Well in Toronto

Toronto’s revenue environment rewards discipline, credibility, and cross-functional alignment. Fractional CSOs thrive here because they can:

• Step into leadership gaps quickly
• Bring pattern recognition from multiple industries
• Support hiring, onboarding, and enablement
• Create structure without overengineering
• Align revenue strategy with people and culture

This mirrors what we see across Digital Reference’s broader work. Organizations increasingly want transparent signals of leadership quality, not inflated titles. 

Closing Thoughts: Revenue Leadership in the Toronto Market

Toronto has built its reputation on measured growth, operational maturity, and credibility-first leadership. The best revenue leaders here understand that scaling sales isn’t about shortcuts—it’s about systems, people, and trust compounding over time.

The fractional CSOs featured in this guide reflect that philosophy. Each brings a distinct approach, but all share a commitment to real execution, thoughtful leadership, and sustainable revenue performance.

At Digital Reference, our mission is to help organizations better understand who they’re hiring, partnering with, and trusting at the leadership level. Through radical transparency, structured references, and context-rich insights, we help companies make smarter decisions about senior talent.

👇 Find more curated insights from Digital Reference:

• Best Fractional CROs in Toronto
• Best Fractional Chief Sales Officer (CSO) Services in Canada
• Best Sales Motivational Speakers in Canada

This list will continue to evolve—as Toronto’s revenue ecosystem does—because great leaders are always building.