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Outbound Account Executive - Retail

Remote / Online - Candidates ideally in
Montreal, Montréal, Province de Québec, Canada
Listing for: Lightspeed
Full Time, Remote/Work from Home position
Listed on 2026-09-12
Job specializations:
  • Sales
    B2B Sales, Business Development
Job Description & How to Apply Below
Location: Montreal

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

  • 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 purchase program to get your personal Macbook

  • Enhanced parental leave to support growing families

  • Fuel your growth. Find your people.

    At Lightspeed, your growth is our priority. We invest in you with continuous learning opportunities, global mobility and benefits designed to support you—all within a driven, diverse and inclusive team that’s passionate about empowering our communities

    #LI-TL2

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