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 recent 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

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📌 Regional Sales Manager – Ontario (Toronto / Waterloo Corridor)
🏢 Leaseweb
📍 Toronto