Enterprise Sales Development Representative - Retail

Lightspeed; Montreal (administrative region); Hybrid; CAD 45,000 - 90,000; Full time

Job summary

A fast-growing tech company in Montreal is seeking an Enterprise Outbound Sales Development Representative to drive revenue growth by generating leads for enterprise retail clients. The ideal candidate has 2–5 years of SaaS sales experience, strong communication skills, and a proven ability to engage stakeholders. This role offers a flexible work environment, competitive compensation, and growth opportunities in a passionate team committed to success.

Benefits

Flexible paid time off

Equity options

Pension plan contributions

Training opportunities

Health and wellness credit

Time off to volunteer

Employee-led networks

Computer purchase program

Enhanced parental leave

Qualifications

• 2–5 years of experience in SaaS outbound sales, preferably with enterprise clients.
• Proven ability to engage enterprise stakeholders in complex sales cycles.
• Fluency in English as a working language is required.

Responsibilities

• Proactively prospecting enterprise retail accounts via multiple channels.
• Building relationships with enterprise-level stakeholders.
• Collaborating with Enterprise Account Executives for lead handoff.

Skills

SaaS outbound sales

Cold-calling

Relationship-building

Communication skills

Entrepreneurial mindset

Job description

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!

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 helping empower retailers.

Our Enterprise Outbound team is in hyper-growth mode, and we need a driven, strategic, and energetic individual who is passionate about helping larger retail businesses grow. If you’re results-driven and excited to join a fast‑growing company, this is the role for you.

What you’ll be doing:

• Proactively prospecting 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.
• As a global company with employees and clients outside of Quebec, 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.

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!

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. 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.

At Lightspeed, we carefully consider a wide range of factors when determining compensation, including your skill set, qualifications, experience, and market data. These considerations can cause your compensation to vary. We reasonably expect the total compensation for this position to be in the range of $45,000 - $90,000 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. This role represents an existing vacancy at Lightspeed. 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.

#LI‑TL2

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.

Lightspeed is an 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.

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. 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.

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 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 handles your information in accordance with our Applicant Privacy Statement.