Retail POS Enterprise Account Executive

Accountabilities:: Drive enterprise sales of modern retail point-of-sale solutions to organizations across the retail and consumer goods sectors. Manage the full sales cycle, developing opportunities from initial discovery and prospecting through solution positioning, negotiation, and closing. Generate new business opportunities through warm leads, existing customer relationships, and proactive prospecting within untapped accounts. Build and maintain trusted relationships with key customer stakeholders, including senior executives, C-suite decision-makers, and operational leaders. Develop strategic account plans aligned with customer priorities, long-term business objectives, and opportunities for technology adoption. Identify growth opportunities within assigned accounts, expanding existing relationships and increasing the value customers derive from their technology investments. Communicate compelling value propositions that demonstrate how modern POS solutions address business challenges, improve retail operations, and support customer goals. Coordinate internal sales, cloud, and other cross-functional resources to develop aligned account strategies and meet customer requirements. Collaborate with broader account teams to ensure consistent engagement, strategic alignment, and effective execution across customer opportunities. Monitor customer needs, account development opportunities, and sales progress to achieve revenue targets and maintain strong customer satisfaction. Contribute to a high-performing enterprise sales team by sharing insights, coordinating initiatives, and maintaining a customer-focused approach. Requirements: At least 6 years of full-cycle sales experience, with a proven ability to manage complex sales opportunities from prospecting through closing. Required: Demonstrated experience selling point-of-sale (POS) solutions, with an understanding of retail technology and the commercial considerations involved in POS sales. Strong consultative selling and business development skills, including the ability to uncover customer needs, qualify opportunities, communicate value, and develop effective sales strategies. Experience building relationships with senior stakeholders and executive decision-makers within enterprise or strategic accounts. Ability to develop and execute account plans that align customer business objectives with technology solutions and long-term growth opportunities. Strong stakeholder management and collaboration skills, with the ability to coordinate a large, extended team of sales and technical resources. Excellent communication, presentation, negotiation, and relationship-building abilities, enabling you to engage effectively with diverse customer audiences. A proactive and results-oriented mindset, with the ability to identify new opportunities, manage multiple priorities, and work effectively in a fast-paced sales environment. Strong strategic thinking and commercial awareness, including the ability to connect technology capabilities to measurable business outcomes. Preferred: Experience in the retail industry or consumer goods sector, particularly in enterprise technology sales. Relevant professional, leadership, volunteer, military, or other experience demonstrating the competencies required for success in the role may also be considered. Benefits: Work arrangement: Remote, home-based position in Canada, with the role listed in Montréal. Employment type: Full-time opportunity focused on enterprise sales and strategic customer relationships. Personalized training and development opportunities to strengthen product knowledge, sales expertise, and industry understanding. Career growth opportunities within a dynamic enterprise sales organization serving major retail and consumer goods customers. The opportunity to work with strategic accounts and engage with senior business leaders on significant retail technology initiatives. Collaborative work environment with access to extended sales and cloud teams to support customer needs and account growth. Exposure to modern POS solutions and enterprise technology initiatives shaping the future of retail. Employee benefits and resources intended to support well-being and work-life balance; specific salary, healthcare coverage, paid leave, commission structure, and other benefit details were not provided in the original posting.