Director of Sales - Retail SaaS Vertical

Software International; Toronto; Hybrid; CAD 150,000 - 160,000; Full time

Job summary

Software International is hiring a Director of Sales for their Retail SaaS Vertical. In this pivotal role, you will lead a customer-focused enterprise sales organization, achieve year-over-year growth, and collaborate with various teams to refine sales strategies. The position offers a competitive salary, remote work opportunities, and a dynamic work culture.

Benefits

Employee Stock Option Plan

Comprehensive employee benefits program

Flexible work location

Qualifications

• 15+ years of enterprise sales experience.
• 10+ years leading a sales team achieving exceptional results.
• Proven track record in selling enterprise solutions.

Responsibilities

• Drive organic growth by achieving strong year-over-year bookings results.
• Lead demand generation activities to build and expand the sales pipeline.
• Collaborate with Product, Marketing, and Customer Success teams.

Skills

Leadership

Consultative Sales

Negotiation

Communication

Presentation

Education

Bachelor's degree in Business Management

MBA

Job description

Director of Sales - Retail SaaS Vertical

Software International (SI) supplies 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 with revenue exceeding $80 billion. They specialize in the acquisition of B2B companies and design, implementation, and support of various B2B software across a wide range of industries.

Role : Director of Sales - SaaS Vertical

Type : Hybrid or Remote if outside of Toronto - Must be able to work EST

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

Job Summary

Reporting directly to the General Manager, the Vice President of Sales will be pivotal in establishing a world-class, customer-focused enterprise sales organization. This role demands outstanding leadership and team-building skills to drive, coach, manage, and mentor your team towards achieving a 30% year-over-year growth in bookings across North America. You will play a crucial role in transforming the sales organization into a more disciplined and consultative selling entity.

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.
• 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.
• 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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