As of November 8, 2026, Jobsy lists 16 regional sales director jobs in Canada. The most active employers are CoStar, Jacobian and Canteen. Skills often requested: sales, sales targets, coaching and negotiation.
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Workday, Inc.: Workday is a leading provider of enterprise cloud applications for finance and human resources, helping customers adapt and thrive in a changing…
8+ YOE2+ MgmtCandidates need several years of enterprise sales experience, including selling to security and technology executives and leading sales teams. Identity, security and access management knowledge, plus experience in team-selling models, is expected.
Sales, Workday, Regulatory compliance, Collaboration, Lead a team, Team leadership
Neo Financial: Neo is a leading financial technology company that’s building a more rewarding financial experience — empowering more Canadians to take control of…
8+ YOE8+ MgmtCandidates need 8+ years of sales management with proven P&L and team development results, strong data analysis skills, and a valid driver's licence. A bachelor's degree is preferred, along with an existing network of sales representatives.
Neo Financial: Neo is a leading financial technology company that’s building a more rewarding financial experience — empowering more Canadians to take control of…
8+ YOE8+ MgmtCandidates need 8+ years of sales management and data analysis experience, plus 7+ years of leadership and negotiation skills. A valid driver's license, willingness to travel, and an existing network of sales representatives are required, and a bachelor's degree is preferred.
8+ YOE5+ MgmtCandidates need 8+ years selling cloud, SaaS, ERP or analytics solutions to CIOs or CTOs, 5+ years leading a sales team, and strong technical credibility in cloud, data, integration and AI.
Sales, Workday, Collaboration, Team leadership, Coaching, Lead a team
5+ YOECandidates need 5+ years of healthcare sales experience with a record of winning new business for complex technology. Radiology or imaging experience and familiarity with RIS/PACS are strongly preferred.
5+ YOECandidates need 5+ years of healthcare sales experience with a strong record of winning new business and selling complex technology. Experience in radiology or imaging environments and knowledge of reporting workflow, RIS/PACS or imaging applications are strongly preferred.
10+ YOE5+ MgmtCandidates need at least 10 years of sales experience, including 5 years managing sales teams, with significant experience in automotive and selling SaaS or cloud-based solutions. They must show a proven record of meeting and exceeding team quotas, strong communication and customer-focused skills, and a structured, process-driven sales approach.
Sales, Sales strategies, Collaboration, Relationship building, Process improvement, Sales targets
CoStar: CoStar Group’s major brands include CoStar, a leading global provider of commercial real estate data, analytics, and news; LoopNet, the most…
5+ YOE3+ MgmtCandidates need five or more years in front-line sales leadership, ideally in digital marketing, advertising or multifamily real estate. They also need three or more years managing a team of five or more and a bachelor's degree.
CoStar: CoStar Group’s major brands include CoStar, a leading global provider of commercial real estate data, analytics, and news; LoopNet, the most…
5+ YOE3+ MgmtCandidates need five or more years in front-line sales leadership, ideally in digital marketing, advertising or multifamily real estate. They also need three or more years managing a team of five or more and a bachelor's degree.
Archistar: Archistar is a global proptech company with offices in the US, Canada, and Australia.
7+ YOECandidates need 7+ years of enterprise SaaS or technology sales experience, with a proven record selling into Canadian municipalities or the public sector. They must know RFPs, RFQs and public procurement, and be able to manage complex, multi-stakeholder sales and explain technology clearly in a business case.
Archistar: Archistar is a global proptech company with offices in the US, Canada, and Australia.
7+ YOECandidates need 7+ years of enterprise SaaS or technology sales, ideally into Canadian municipalities or the public sector. They must have strong pipeline creation, experience with RFPs and public procurement, and the ability to explain technology as a clear business case to senior government leaders.
Hello World Recruitment: Hello World Recruitment is the Canadian recruitment firm dedicated to Insurance professionals in North America.
3+ YOECandidates need 3+ years of sales or business development experience, with 2+ years of field sales preferred. Insurance or financial services experience is an asset, along with strong communication, negotiation and CRM skills, regular travel and a valid driver's licence.
4+ YOECandidates need at least 4 years of hunter-style B2B sales experience in a fast-paced setting with structured sales management. They should show strong negotiation skills, relationship-building ability and experience with financial projections for long-term contracts.
4+ YOECandidates need at least 4 years of hunter-style B2B sales experience, strong negotiation and relationship skills, and the ability to win over senior decision makers. They also need experience building financial projections for long-term contracts and a valid driver's licence.
Candidates need a solid understanding of the life insurance business and its products, plus a valid LLQP licence. Strong communication, presentation and interpersonal skills are essential, and fluency in both French and English is required.
5+ YOE3+ MgmtCandidates need five or more years in front-line sales leadership, ideally in digital marketing or advertising sales, and three or more years managing a team of five or more. They also need a bachelor's degree, a valid driver's licence with a clean driving record, and current authorization to work in Canada.