Enterprise Sales Director - Strategic, Consumer Business Services

Sierra is seeking a full-time, remote Enterprise Sales Director in Canada to lead complex, multi-geography deals within its Consumer Business Services vertical. The role requires 10-12+ years of enterprise sales experience, including managing a $1M+ quota and closing multi-million-dollar contracts. Candidates must demonstrate deep C-suite relationships and the ability to structure sophisticated deals across various industries such as logistics, real estate, and energy. The position involves engaging directly with Sierra’s co-founders and leveraging AI tools to optimize the sales cycle while maintaining high-value customer relationships.

Key details

• Full-time, remote position based in Canada.
• Requires 10-12+ years of enterprise sales experience.
• Focuses on closing multi-million-dollar, multi-stakeholder deals.
• Involves managing a quota of $1M or more.
• Requires deep C-suite relationships and executive communication skills.