Outbound Account Executive - Toronto
About The Position
This is a true ownership role where you will 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.
Requirements
- 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
Nice To Haves
- Experience with Salesforce.com
- Experience with SaaS
- Retail experience
Responsibilities
- 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.
Benefits
- Flexible work environment
- Culture that celebrates performance
- Career growth opportunities
- Flexible paid time off and remote work policies
- Equity options
- Contributions to your pension plan
- Training opportunities
- Health and wellness credit
- Time off to volunteer
- Interest groups, employee led networks, social committees to sponsored sports teams
- Computer purchase program
- Enhanced parental leave
- Medical insurance
- Dental insurance
- Wellness insurance
- Life insurance
- Disability insurance
- RRSP plan and match
- Paid parental leave top-up
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What This Job Offers
Job Type
Full-time
Career Level
Mid Level
Education Level
No Education Listed
