Outbound Sales Development Representative - Retail

Lightspeed is looking for a highly motivated Outbound Sales Development Representative to join our North American Outbound Sales team. You will 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.

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

• 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.
• As a global company with employees and clients outside of Quebec, fluency in English as a working language is required.

• 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.

• Adaptable 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.
• Flexible paid time off and work from home policies.
• Equity options.
• 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 Mac Book.
• Enhanced parental leave to support growing families.

$40,000 - $80,000 CAD (Ontario). Compensation may vary based on your skills, experience, and market data.