Director of Sales

Job summary

Lead sales and account management activities across Canada for a POS technology business, focusing on strengthening sales processes and strategic customer relationships. Manage and coach a team of Regional Account Managers while serving as a senior point of contact for key retail customers.

Job details

Role Summary: The Director of Sales will lead sales and account management activities across Canada for an established POS technology business. This is a hands-on leadership role focused on strengthening the sales process, developing strategic customer relationships, and creating a more consistent approach to account management and sales execution. The ideal candidate is a strong sales leader and account manager who enjoys building structure, coaching a small team, and working closely with customers to identify and develop new business opportunities. Key Responsibilities: • Build and implement a consistent approach to account planning, pipeline management, forecasting, customer reviews, and sales reporting. • Manage and grow relationships with key Canadian retail customers, serving as a senior point of contact and trusted advisor. • Develop account plans that identify customer priorities, upcoming initiatives, expansion opportunities, and areas where the company can add additional value. • Build relationships with senior IT, operations, technology, and business stakeholders within key customer accounts. • Lead regular customer and business reviews, ensuring priorities, opportunities, commitments, and next steps are clearly defined. • Identify opportunities to grow existing accounts through additional software, deployments, services, and new initiatives. • Support the pursuit of select new customers across the Canadian retail market, managing opportunities through qualification, solution development, negotiation, and close. • Lead, coach, and develop two Regional Account Managers covering Eastern and Western Canada. • Work closely with the Regional Account Managers to develop account strategies, prioritize opportunities, and improve sales execution. • Partner with Product, Engineering, Implementation, Project Management, Customer Success, Support, Service, Marketing, and Finance to coordinate customer needs and resolve issues. • Bring customer feedback and market intelligence back to the organization to help identify product, service, and commercial opportunities. • Help customers understand how the company's POS technology can support their operational and business objectives. • Establish greater sales discipline around opportunity management, forecasting, pipeline quality, and follow-up. • Help introduce a more structured commercial approach while working respectfully within a long-tenured and established company culture. • Spend significant time with customers and the sales team, providing hands-on leadership and support throughout the sales process. Core Competencies: • Bachelor’s degree or equivalent combination of education and relevant experience. • 7+ years of B2B sales, strategic account management, or sales leadership experience. • Experience managing and developing sales professionals, ideally within a small team environment. • Experience with POS, retail technology, payments, enterprise software, or a closely related technology sector. • Strong understanding of the needs and challenges of retailers, particularly multi-site or enterprise customers. • Proven ability to build and maintain strong customer relationships and manage complex sales cycles. • Strong account management skills, including account planning, customer reviews, opportunity development, and relationship mapping. • Comfortable engaging with senior customer stakeholders and communicating with professionalism and confidence. • Strong commercial judgment with experience in pipeline management, forecasting, negotiation, and closing. • Hands-on, collaborative leadership style with a willingness to work alongside the team and stay close to customers. • Ability to introduce structure and process without creating unnecessary bureaucracy. • Strong interpersonal skills and the ability to work effectively within a long-tenured, established organization. • Low-ego, team-oriented approach with strong follow-through and accountability. • Builder mentality with the ability to improve and establish sales practices while remaining hands-on in the business. • Based in Toronto preferred; Calgary considered. Approximately 25–30% travel required. • Canadian work authorization required; no sponsorship available.

What you’ll do

Lead sales and account management activities across Canada for a POS technology business, focusing on strengthening sales processes and strategic customer relationships. Manage and coach a team of Regional Account Managers while serving as a senior point of contact for key retail customers.

Requirements

Requires a bachelor's degree and over 7 years of experience in B2B sales or sales leadership, specifically within the POS or retail technology sector. Must have Canadian work authorization and the ability to travel approximately 25-30%.

Listed skills

• Forecasting · Preferred
• Negotiation · Preferred
• Coaching · Preferred

Other relevant skills

Identified from the job description. Confirm important requirements above.

• B2B Sales
• Strategic Account Management
• Sales Leadership
• POS Technology
• Pipeline Management
• Forecasting
• Account Planning
• Relationship Mapping
• Retail Technology
• Negotiation
• Coaching
• Commercial Judgment

Job areas

• Sales
• Management & Leadership
• Retail
• Software
• Technology