Senior Outbound Account Executive - Retail

About Lightspeed

Powering the businesses that are the backbone of the global economy, Lightspeed's one‑stop commerce platform helps merchants innovate to simplify, scale, and provide exceptional customer experiences. Our cloud commerce solution transforms and unifies online and physical operations, multichannel sales, expansion to new locations, global payments, financial solutions, and connection to supplier networks.

Founded in Montréal, Canada in 2005, Lightspeed is dual‑listed on the New York Stock Exchange (NYSE: LSPD) and Toronto Stock Exchange (TSX: LSPD). With teams across North America, Europe, and Asia Pacific, the company serves retail, hospitality, and golf businesses in over 100 countries.

Lightspeed is building communities through commerce, and we need people from all backgrounds and lived experiences to do that. We were founded in 2005, in Montreal’s gay village and our original members were all part of the LGBTQ+ community. The ethos of our business has been about inclusion from the very beginning, and we strive to provide a workplace where everyone belongs.

Lightspeed handles your information in accordance with our Applicant Privacy Statement.

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Role: Senior Account Executive, Outbound (Retail)

Lightspeed is looking for a Senior Account Executive, Outbound to join our high‑performing Retail sales team in North America. This is a hybrid role (3 days / week in our Toronto office) that receives support from our SDR team with expectations of self‑generating additional leads in order to over‑achieve on KPIs. AE’s will be generating a pipeline through prospecting, booking meetings and owning the sales process from initial outreach to demo and close.

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What You’ll Be Doing

• Pipeline Development & Sales: Leverage a combination of phone, email, and social outreach to generate new business opportunities. Build relationships, initiate conversations, and identify client needs in the retail sector.
• Lead & Manage the Sales Process: Own the sales cycle from initial outreach to closing deals, including leading demo presentations and negotiating contracts. Manage multiple deals simultaneously within Salesforce.
• Team Collaboration: Work closely with the wider sales and marketing teams to achieve collective business goals. Collaborate with leadership on pricing negotiations, optimizing touchpoints, and refining sales strategies.
• Performance & KPI Management: Accurately forecast sales pipeline and meet monthly and quarterly revenue targets. Track and report key sales metrics (e.g., meetings booked, pipeline health, deal progression).
• Market Intelligence: Provide feedback on market trends, customer challenges, and competitor strategies to help shape the company's direction and offerings.

And a little bit of…

• Contributing as part of the wider team to achieve organisational objectives even if this means doing things that aren’t strictly within the scope of your role

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What You Need To Bring

• 3‑5 Years Sales Experience: You have at least 3‑5 years of proven sales experience in an outbound B2B sales role, ideally within the retail sector or SaaS industry.
• Full‑Cycle Sales Expertise: Experience managing all aspects of the sales cycle, from prospecting to closing.
• Track Record of Success: Demonstrated history of consistently hitting or exceeding sales targets.
• Pipeline Forecasting: Experience with forecasting sales and managing KPIs on a daily, weekly, and monthly basis.
• Self‑Motivated & Results‑Driven: You are a driven and goal‑oriented individual with a strong desire to succeed in a high‑performance environment.
• Fluency in English as a working language (required for this position).

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What Will Help You Succeed

• Professional Communication: Confident in engaging with C‑level executives and senior decision‑makers.
• Hunter Mentality: You are proactive, comfortable with outbound prospecting, and understand that success comes from volume and persistence.
• Resilience & Positivity: You embrace challenges, learn from rejection, and maintain a positive mindset.
• Growth Mindset: You thrive in an environment where feedback is valued, and you continuously work to improve your skills.
• Team Player: While you drive your own success, you contribute to the collective success of the team with a collaborative mindset.

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How You Will Be Measured On KPI’s

• Revenue Targets: Consistently meet or exceed your monthly and quarterly revenue goals.
• Pipeline Management: Effectively generate, nurture, and close opportunities to achieve your sales objectives.
• Team Contribution: Play an active role in driving the growth of the business, offering valuable market insights and collaborating on key initiatives.

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What’s in it for you?

Come live the Lightspeed experience…

• Ability to do your job in a truly flexible hybrid environment (3 days/week in office)
• Genuine career opportunities in a company that’s creating new jobs everyday
• Work in a team big enough for growth but lean enough to make a real impact

…and enjoy a range of benefits that’ll keep you happy, healthy and (not) hungry:

• Lightspeed RSU program (we are all owners)
• Unlimited paid time off policy
• Flexible working policy
• Health insurance
• Health and wellness benefits
• Possibility for transit fees to be covered
• Paid leave assistance for new parents
• LinkedIn Learning
• Volunteer day

Compensation

We reasonably expect the total compensation for this position to be in the range of $62,000 – $104,000 CAD. Lightspeed also provides a variety of employee benefits including, but not limited to, medical, dental, wellness, life and disability insurance, RRSP plan and match, paid parental leave top‑up, and paid time off.

Please note that this compensation information is solely for candidates hired to perform work within Ontario and reflects the amount Lightspeed is willing to pay at the time of this posting.

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Application Note

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!

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Equal Opportunity & Inclusion

Lightspeed is a proud equal opportunity employer and we are committed to creating an inclusive and barrier‑free workplace. Lightspeed welcomes and encourages applications from people with disabilities. Accommodations are available on request for candidates taking part in all aspects of the selection process.

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Agency Notice

To all recruitment agencies: Lightspeed does not accept unsolicited agency resumes. If we have not directly engaged your company in writing to supply candidates for a specific vacancy, Lightspeed will not be responsible for any fees related to unsolicited resumes.

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Next Steps

Obviously, this has to be mutually beneficial: we want you to step into a role you love, and we want to offer you a place you’re proud to come to every day. For a glimpse into our world check out our career page here.

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