Regional Sales Manager – Ontario (Toronto / Waterloo Corridor)

What is the role about?

Leaseweb Canada is building its Ontario sales presence from the ground up, and we are looking for a Regional Sales Manager in Ontario to lead this expansion.

This is a founder-style, quota-carrying role for someone who wants to build a territory rather than inherit one. You will define and execute the go-to-market strategy for Ontario, generate your own pipeline, close new business, and lead a small but high-potential team.

The initial team consists of two employees (Account Manager / Business Development Manager) with the expectation that it will grow as the region develops.

The role will focus primarily on two customer segments:

• Tech companies, including SaaS scale-ups, AI and GPU infrastructure users, and businesses with data residency or compliance-driven infrastructure needs.

• MSPs and resellers that are building or expanding infrastructure and AI solutions for their clients.

Key responsibilities

• Define and execute the go-to-market strategy for Ontario, prioritizing the Tech and MSP/Reseller segments.

• Carry a personal sales quota by generating and closing new business.

• Build a pipeline from scratch through proactive prospecting, networking, partnerships, and market development.

• Manage, coach, and develop the team, while contributing to future hiring decisions as the team grows.

• Build relationships with MSPs, resellers, technology partners, and integrators to create new sources of pipeline.

• Represent Leaseweb within Ontario’s tech and MSP ecosystem by actively participating in industry events, conferences, and networking opportunities.

• Monitor quota attainment, pipeline health, and key performance indicators.

• Provide the CEO with regular performance updates, market intelligence, and competitive insights.

• Collaborate closely with the Montreal-based leadership and operations teams, including regular travel to Montreal.

What we’re looking for:

• Proven B2B sales experience, ideally in cloud infrastructure, hosting, IT services, or a related technology sector.

• A strong track record of building pipeline and developing a new or underpenetrated territory.

• An entrepreneurial mindset and the ability to operate effectively with limited structure.

• Experience selling to or partnering with MSPs, resellers, and/or tech and SaaS companies.

• Demonstrated ability to generate and close business personally while leading and coaching a small team.

• Strong relationship-building, networking, and communication skills.

• Genuine comfort representing the company at industry events and developing a visible market presence.

• A results-driven approach with strong ownership, autonomy, and commercial judgment.

• Based in—or willing to be based in—the Toronto–Waterloo corridor, with flexibility to travel regularly to Montreal.

Benefits included:

• Participation in the annual company bonus scheme

• Group RRSP with employer contribution

• Internet allowance

• 100% remote

• 4 weeks of Vacation + 5 mobile days per year

• Group insurance + telemedicine + health care management account.

• Personalized learning platform offering a variety of courses and training

• Fun events year-round – from virtual pub quizzes to summer parties, company runs, quarterly hackathons, and much more

• A multicultural work environment (our colleagues are from over 60 countries!) in a company where you can truly make a difference.

• Travel expenses, including mileage, are covered

Ready for the next step?

If you’d like to apply, please do so online. To learn more about us, follow us on LinkedIn or Instagram to get an inside look at life at Leaseweb.

We directly source all candidates – any unsolicited profiles received from recruitment agencies will be treated as direct applications