Enterprise Sales Director

2 months ago

Toronto, Ontario, Canada Software International Full time

Software International is a leading provider of technical talent to Fortune 100/500/1000 companies in Canada. Our client is a large, publicly traded software company with operations in 30+ countries worldwide, generating revenue exceeding $80 billion. They specialize in the acquisition of B2B companies and the design, implementation, and support of various B2B software across a wide range of industries.

Role: Sales Director - Retail SaaS

Location: Greater Toronto Area, Canada

Type: Remote, with the ability to work EST

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

Job Summary

The Sales Director will play a pivotal role in establishing a world-class, customer-focused enterprise sales organization, focusing on the Retail SaaS space. 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.

Key Responsibilities

  • Drive organic growth by achieving strong year-over-year bookings results.
  • Actively lead demand generation activities to build and expand the sales pipeline.
  • Set, meet, and exceed quarterly and annual sales quotas and objectives.
  • Collaborate with Product, Marketing, and Customer Success teams to align sales activities with product strategies.
  • Foster a sales culture focused on delivering exceptional customer experiences.
  • Continuously monitor and adjust the sales coverage model to ensure a strong ROI on sales investments.
  • Measure, coach, mentor, and top-grade the sales team to exceed targets.
  • Report monthly on sales progress, activities, highlights, challenges, and insights.
  • Establish and reinforce sales policies, consultative selling processes, and account planning standards.
  • Ensure data accuracy in sales records for projections up to 12 months.
  • Effectively manage customer and sales team escalations in collaboration with peers.
  • Conduct in-depth market research and competitor analysis to refine sales practices.
  • Work collaboratively with peers to address and meet customer needs.

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.
  • Self-starter thriving in a fast-paced environment with acute attention to detail and customer care.
  • Excellent presentation, negotiation, and executive engagement skills.
  • Superior communication and active listening skills.
  • Experience in developing compensation plans and coaching value-based sales methodologies.
  • Proven ability in implementing and delivering on account planning.
  • Recognized for high drive, business acumen, work ethic, and metric orientation.
  • Willingness and ability to travel more than 20% of the time.

What's In It For You?

  • Opportunity to work with a dynamic, innovative, passionate, and entrepreneurial team.
  • Open and inclusive company culture.
  • Competitive salary.
  • Participation in the Employee Stock Option Plan.
  • Comprehensive employee benefits program.
  • Flexible work location across North America as long as available during Eastern Standard Time zone business hours.

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