Director of Sales

Vaughan Executive Partners, LLC; Toronto; On-site; CAD 120,000 - 180,000; Full time

Job summary

Vaughan Executive Partners, LLC seeks a Director of Sales to lead Canada-wide sales and account management for an established POS technology business. This hands-on leadership role emphasizes building structure, coaching a small team, and close customer collaboration to identify new opportunities.

You will drive account planning, forecast accuracy, and cross-functional alignment with Product, Engineering, and Customer Success to deliver value at scale. Travel 25–30% is expected.

Qualifications

• 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.

Responsibilities

• Lead sales and account management across Canada, building a consistent sales process.
• Manage and grow relationships with key Canadian retail customers.
• Develop account plans identifying priorities, upcoming initiatives, expansion opportunities, and areas for value.
• Coach two Regional Account Managers and drive sales execution.
• Collaborate with Product, Engineering, Implementation, and other teams to align solutions with customer needs.
• Lead regular customer reviews, forecast pipeline, and ensure next steps are defined.

Skills

B2B sales

Strategic account management

Sales leadership

Team coaching

Relationship building

Forecasting

Pipeline management

Negotiation

Account planning

Education

Bachelor’s degree or equivalent

Job description

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.