Enterprise Sales Development Representative - Retail

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Are you actively looking for a new opportunity? Or just checking the market? Well… you might just be in the right place! Lightspeed is looking for a highly motivated Enterprise Outbound Sales Development Representative to join our North American Outbound Sales team. You’ll help drive revenue growth by generating and qualifying leads for enterprise retail clients, acting as the first point of contact and enabling retailers to grow.

What You’ll Be Doing

• Proactively prospect enterprise retail accounts via phone, email, social media, and other outbound channels.
• Reaching out to enterprise-level stakeholders (Directors and above) to understand their challenges and build strong relationships.
• Collaborating with Enterprise Account Executives to ensure smooth lead handoff and strategic follow‑up.
• Providing feedback to marketing and sales teams based on prospect conversations to help refine outbound strategies.
• Consistently achieving monthly, quarterly, and annual outbound sales goals in a high‑velocity environment.

What You’ll Be Bringing

• 2–5 years of experience in SaaS outbound sales, preferably with enterprise or mid‑market retail clients.
• Proven ability to cold‑call, email, and engage enterprise stakeholders in complex sales cycles.
• Strong communication and relationship‑building skills, with the ability to explain complex solutions to multiple stakeholders.
• Tech‑savvy, strategic, and comfortable navigating enterprise accounts.
• Entrepreneurial mindset, bias toward action, and the ability to adapt quickly in a fast‑growing business.
• Fluency in English as a working language is required for this position.

Even Better If You Have

• Experience selling into enterprise retail clients.
• Familiarity with POS systems or other software platforms in large organizations.
• Experience with consultative selling approaches such as MEDDPICC or BANT.

What’s in it for you?

• 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.

Benefits

• Flexible paid time off and remote work policies.
• Equity options, because this is your company too.
• Contributions to your pension plan.
• Training opportunities to grow your skills and career.
• Health and wellness credit.
• Time off to volunteer and give back to your community.
• Interest groups, employee‑led networks, social committees, and 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.

$45,000 - $90,000 CAD. The total compensation for this position may vary based on skill set, qualifications, experience, and market data. Lightspeed also provides a variety of employee benefits including medical, dental, wellness, life and disability insurance, RRSP plan and match, paid parental leave top‑up, and paid time off.

Lightspeed uses artificial intelligence–enabled tools to support certain aspects of the recruitment process; all hiring decisions are made by our recruiting and hiring teams. This role represents an existing vacancy at Lightspeed.

To all recruitment agencies: Lightspeed does not accept unsolicited agency resumes unless we have directly engaged your company in writing to supply candidates for this vacancy. Lightspeed is a proud equal opportunity employer and we are committed to creating an inclusive and barrier‑free workplace. We welcome and encourage applications from people with disabilities. Accommodations are available on request for candidates taking part in all aspects of the selection process.

Where to from here?

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. Lightspeed is building communities through commerce, and we need people from all backgrounds and lived experiences to do that.

Who We Are

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 u