Outbound Account Executive - Retail

Role overview

This is an outbound account executive position focused on the retail segment at Lightspeed, a commerce platform that enables small and medium-sized businesses to compete effectively in their markets. You will own your entire sales pipeline, from initial outreach through deal closure, targeting a defined market segment with a structured outbound strategy.

Key responsibilities

Generate and manage your sales pipeline end-to-end within your assigned territory, using targeted outreach to create opportunities and close deals.
Execute outbound strategy across defined market segments, developing and continuously testing cadences to optimize your approach.
Conduct discovery conversations and product demonstrations using a consultative approach to identify customer challenges and demonstrate clear business value.
Maintain accurate pipeline management in Salesforce, forecast reliably, and consistently meet monthly and quarterly revenue targets.
Evaluate opportunities using criteria such as gross transaction volume, business model, and purchasing timeline to prioritize high-value prospects.
Work with sales development representatives to convert outbound interest into qualified deals and closed revenue.
Negotiate pricing and deal terms strategically while protecting margin and driving deals forward to completion.

Requirements

Proven experience building pipeline through outbound prospecting and converting cold outreach into genuine sales opportunities.
Demonstrated ability to manage and forecast a sales pipeline while consistently meeting or exceeding targets.
Track record as a top performer with clear, quantifiable results you can articulate.
Comfort owning the complete sales cycle from first contact to closed deal without relying on inbound leads.
Skill in conducting structured discovery, guiding prospects through the buying process, and managing complex negotiations.
Ability to accept constructive feedback on deals and confidently defend your pipeline forecast.
Motivation to grow your career within Lightspeed as part of a high-performance sales organization.

What makes this role worth considering

This position is hybrid, requiring in-office attendance on Tuesdays, Wednesdays, and Thursdays from the Montreal office. You’ll work within a team that values outbound selling as a skill rather than a volume exercise, prioritizing quality execution and deep customer understanding. Lightspeed offers career growth opportunities, equity options, flexible paid time off, training programs, wellness credits, volunteer time, and a computer purchase program, along with enhanced parental leave and employee-led community networks.