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Enterprise SaaS Sales Director

Job in Winnipeg, Manitoba, Canada
Listing for: Jobgether
Full Time position
Listed on 2026-11-04
Job specializations:
  • Sales
    SaaS Sales, Director of Sales, VP of Sales, Account Manager
Job Description & How to Apply Below
Lead enterprise SaaS revenue across North America from Canada, combining strategic sales leadership with hands-on deal execution. This fully remote opportunity centers on scaling enterprise growth.
As Sales Leader, Enterprise, you will oversee Enterprise Account Executives and own segment performance. You will coach senior sellers, navigate competitive sales cycles, and strengthen relationships with large organizations. The role also shapes go-to-market strategy, sales methodology, and coordinated customer acquisition with Product, Marketing, Solutions Engineering, and Professional Services.

Key Responsibilities:

Own Enterprise segment revenue, growth, performance, and sales target achievement
Lead complex sales cycles and support strategic account closures
Hire, onboard, scale, and develop Enterprise Account Executives
Reinforce methodology through coaching, experimentation, and consistent execution
Align cross-functional teams around enterprise acquisition and repeatable growth
Requirements:
Led SaaS Enterprise Account Executives beyond $100 million annual recurring revenue
Managed teams delivering at least $5 million in annual revenue
Helped win $1 million-plus SaaS deals with publicly traded companies

Experience with pipeline, qualification, forecasting, negotiation, and positioning
Based in Canada and comfortable working remotely
Bring enterprise SaaS leadership, strategic deal expertise, and team development strength to Canada’s remote sales leadership market.
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