Outbound Account Executive - Retail

Hi there! Thanks for stopping by 👋 Are you actively looking for a new opportunity? Or just checking the market? Well… you might just be in the right place! This is a true ownership role. You’ll build and close your own pipeline, working a defined market segment with a strong outbound motion. From first touch to close, you’re responsible for driving deals forward through structured discovery, tailored demos, and disciplined deal strategy. You’ll be part of a team that treats outbound as a skill, not a volume game- performance comes from understanding the customer, controlling the sales process, and consistently executing at a high level. Lightspeed gives SMBs tools to compete with big box stores; and win. You’ll be at the forefront of those conversations. This role is hybrid, based out of our Toronto office (on Spadina), with in-office days every Tuesday, Wednesday, and Thursday. What you’ll be doing: - Own your pipeline end-to-end - from generating opportunities through targeted outreach to closing and expanding deals within your territory. - Drive outbound strategy into defined market segments, leveraging structured cadences while continuously testing and optimizing your approach. - Lead high-impact discovery and product demos - running consultative, screen-share sessions that uncover real business challenges and tie directly to value. - Manage a complex sales pipeline using...