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 Salesforce, maintaining accurate forecasts and consistently delivering against monthly and quarterly targets. - Qualify and prioritize opportunities effectively using key criteria such as GTV, business model, and buying timeline to focus on high-value deals. - Partner closely with SDRs to convert outbound interest into qualified opportunities and ultimately closed revenue. - Collaborate cross-functionally with leadership and peers to refine strategy, share insights, and elevate overall team performance. - Navigate pricing and negotiations with confidence, using structured deal strategy to protect value while driving deals forward. - Consistently exceed targets, taking ownership of your performance and contributing to broader team success. What you need to bring: - You’ve built pipeline through an outbound motion and know how to turn cold outreach into real opportunities - You understand how to manage and forecast a pipeline, and you consistently hit or exceed your targets - You’ve been a top performer before and can clearly speak to the results behind it - You’re comfortable owning the full sales cycle from first touch to close - You create your own momentum instead of waiting on inbound; you are not an ‘order taker’ - You know how to run strong discovery and guide deals forward with structure and intent - You’re comfortable being challenged on your deals and can clearly defend your forecast - You’re motivated to grow your career at Lightspeed Commerce and be part of a high-performance team Even better if you have, but not necessary: - Experience with Salesforce.com http://Salesforce.com - Experience with SaaS - Retail experience We know that people are more than what’s on their CV. If you’re unsure that you have the right profile for the role... hit the ‘Apply’ button and give it a try! Be a changemaker You’ll enjoy: - A flexible work environment that empowers you to do your best work - A culture that celebrates performance - The chance to make an impact in a team that’s big enough for career growth, but lean enough to make your voice heard - Career-defining opportunities Plus benefits designed to keep you happy, healthy and fulfilled. - Flexible paid time off and remote work policies - Equity options, because this is your company too - Contributions to your pension plan. Your future matters - Training opportunities to grow your skills and career - Health and wellness credit so you feel your best - Time off to volunteer and give back to your community - Interest groups, employee led networks, social committees to sponsored sports teams - Computer purch...