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 setting.
- 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.
- Solid 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.

📌 Director of Sales (Greater Toronto Area)
🏢 Vaughan Executive Partners
📍 Greater Toronto Area