Mid-Market Sales Development Representative (Retail)

TL;DR

Mid-Market Sales Development Representative (Retail): Generating and qualifying leads for enterprise retail clients with an accent on outbound prospecting and stakeholder engagement. Focus on cold calling, strategic lead handoff to Account Executives, and driving revenue growth in a high-velocity environment.

Location: North American Outbound Sales team

Company

Lightspeed is a cloud commerce platform that helps merchants simplify and scale their online and physical operations across retail, hospitality, and golf businesses.

What you will do

• Proactively prospect enterprise retail accounts via phone, email, and social media.
• Engage Directors and above to understand business challenges and build strong relationships.
• Collaborate with Enterprise Account Executives to ensure smooth lead handoff and strategic follow-up.
• Provide feedback to marketing and sales teams to help refine outbound strategies.
• Consistently achieve monthly, quarterly, and annual outbound sales goals.

Requirements

• 2–5 years of experience in SaaS outbound sales, preferably with mid-market retail clients.
• Proven ability to cold-call and engage enterprise stakeholders in complex sales cycles.
• Strong communication and relationship-building skills.
• Entrepreneurial mindset with a bias toward action.
• Fluency in English as a working language is required.
• Alignment with the North American region.

Nice to 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.

Culture & Benefits

• Flexible work environment with remote work policies.
• Equity options and contributions to a pension plan.
• Health and wellness credits.
• Continuous training and learning opportunities for career growth.
• Enhanced parental leave and time off to volunteer.
• Computer purchase program for personal Macbooks.