Director of Sales - Retail SaaS Vertical

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

Job summary

An established industry player is seeking a dynamic Director of Sales to lead their retail SaaS vertical. This pivotal role involves establishing a world-class sales organization focused on customer satisfaction and driving significant growth across North America. You will mentor and coach a talented team, ensuring they exceed sales targets while fostering a culture of exceptional service. With a competitive salary, comprehensive benefits, and opportunities for professional growth, this position offers a chance to make a substantial impact in a fast-paced, innovative environment. If you're a results-oriented leader with a passion for sales, this is the perfect opportunity for you.

Benefits

Employee Stock Option Plan

Comprehensive Employee Benefits Program

Flexible Work Location

Open and Inclusive Company Culture

Qualifications

• 15+ years of enterprise sales experience with a strong consultative approach.
• Proven ability to lead sales teams and develop top talent.

Responsibilities

• Drive growth by achieving strong year-over-year bookings results.
• Lead demand generation activities and collaborate with teams.

Skills

Enterprise Sales Experience

Leadership Skills

Consultative Selling

Market Research

Negotiation Skills

Communication Skills

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.