About The Position
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.
Requirements
- 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.
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.
Benefits
- 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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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
