Enterprise Sales Director for Retail SaaS

3 days ago


Old Toronto, Canada Software International Full time
About the Role

Software International is seeking a seasoned sales leader to spearhead our enterprise sales efforts in the retail SaaS space. This is an exciting opportunity for a highly motivated and experienced individual to lead a high-performing sales team and drive significant growth.

Salary: $150,000 - 160,000/year + commissions + bonus + benefits + vacation + discounted company equity purchase + RRSP matching + opportunity for growth within company

Job Description

The Sales Director will report directly to the General Manager and be responsible for establishing a world-class, customer-focused enterprise sales organization. This role demands outstanding leadership and team-building skills to drive, coach, manage, and mentor the sales team towards achieving a 30% year-over-year growth in bookings across North America.

  1. Lead demand generation activities to build and expand the sales pipeline.
  2. Set, meet, and exceed quarterly and annual sales quotas and objectives.
  3. Collaborate with Product, Marketing, and Customer Success teams to align sales activities with product strategies.
  4. Foster a sales culture focused on delivering exceptional customer experiences.
  5. Continuously monitor and adjust the sales coverage model to ensure a strong ROI on sales investments.
  6. Measure, coach, mentor, and top-grade the sales team to exceed targets.
  7. Report monthly on sales progress, activities, highlights, challenges, and insights.
  8. Establish and reinforce sales policies, consultative selling processes, and account planning standards.
  9. Ensure data accuracy in sales records for projections up to 12 months.
  10. Effectively manage customer and sales team escalations in collaboration with peers.
  11. Conduct in-depth market research and competitor analysis to refine sales practices.
About You
  • Bachelor's degree in Business Management with 15+ years of enterprise sales experience; MBA is an asset.
  • At least 10+ years of experience leading a sales team and achieving exceptional results.
  • Strong consultative sales acumen with a client-focused leadership style.
  • Prior experience working with retail sector SaaS or retail marketing.
  • Proven track record in selling enterprise solutions and building strong industry relationships.
  • Demonstrated ability to attract, develop, and retain top sales talent.
  • High-energy, results-oriented, and competitive yet humble approach to market success.
  • Excellent presentation, negotiation, and executive engagement skills.
  • Experience in developing compensation plans and coaching value-based sales methodologies.
  • Proven ability in implementing and delivering on account planning.
  • Flexible work location across North America as long as available during Eastern Standard Time zone business hours.


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