Strategic Outbound Account Executive

Lightspeed; Montreal; On-site; CAD 75,000 - 100,000; Full time

Job summary

A dynamic technology company in Montreal is looking for a Strategic Account Executive to drive revenue by identifying and closing strategic deals with new clients in retail. This role requires over 4 years of outbound sales experience, a strong background in IT solutions, and proficiency in CRM tools like Salesforce. The ideal candidate will have exceptional negotiation and presentation skills, and fluency in English is required. Join a culture that values flexibility and career growth.

Benefits

Flexible paid time off

Equity options

Contributions to pension plan

Training opportunities

Health and wellness credit

Volunteer time off

Employee-led networks

Computer purchase program

Enhanced parental leave

Qualifications

• 4+ years of experience in direct, outbound sales with exceeding targets.
• Experience in software sales, e-commerce, or related technology sectors.
• Ability to foster trust with decision-makers.

Responsibilities

• Identify and pursue new business opportunities with retail prospects.
• Craft and execute sales strategies to win key retail accounts.
• Deliver demonstrations of Lightspeed's products.

Skills

Outbound sales experience

IT solutions sales

Negotiation skills

Critical thinking

Presentation skills

Emotional intelligence

CRM proficiency (Salesforce)

Fluency in English

Tools

Salesforce

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!

We’re looking for a Strategic Account Executive to join our sales team in NOAM. As a Strategic Account Executive focused on new business, you will be at the forefront of our company's growth in Retail, driving revenue by identifying, pursuing, and closing strategic deals with high‑value new clients in the retail network division. This role demands a proactive and results‑oriented professional, with a demonstrated ability to consistently exceed sales targets within a direct sales environment. You will act as a trusted advisor, understanding potential clients' complex business needs and delivering tailored solutions that resonate and close.

What you'll be doing:

• Proactively spot high‑potential retail prospects and show how Lightspeed optimises operations and elevates guest satisfaction.
• Craft and execute sales strategies to win key retail accounts using Lightspeed’s POS, online ordering, and inventory tools.
• Deliver compelling demonstrations that highlight how Lightspeed streamlines workflows and enhances guest experiences.
• Guide complex deals from first contact through negotiation and closing, showcasing Lightspeed’s integrated payments and efficiency.
• Consistently surpass quarterly and annual goals, driving adoption of Lightspeed’s transformative retail technology.
• Cultivate trust with owners, managers, and decision‑makers, aligning Lightspeed solutions with their unique needs.
• Understand business goals and pain points, leveraging Lightspeed’s analytics and reporting to create seamless onboarding and long‑term success.

And a little bit of…

• Work on other sales/marketing campaigns designed to improve the customer experience as well as grow Lightspeed MRR in the process.
• Maintain accurate records of sales activities and prospect interactions within the CRM system.
• Contributing as part of the wider team to achieve organisational targets, even if this means doing things that aren’t strictly within the scope of your role.

What you need to bring:

• 4 years+ experience in direct, outbound sales with a proven record of managing the entire sales cycle and exceeding targets.
• Experience in IT solutions, software sales, e‑commerce, cloud applications, SaaS, POS, retail, or related technology sectors.
• Expertise in leading high‑value negotiations and securing strategic deals.
• Proficient critical thinking skills to assess complex situations and deliver effective, results‑oriented solutions.
• Exceptional verbal and written presentation skills to engage and persuade senior stakeholders.
• Skilled at fostering trust with decision‑makers through emotional intelligence and active listening.
• CRM & Pipeline Management: Proficient in Salesforce or similar tools to track leads and streamline sales processes.
• Thrives in fast‑paced, evolving environments with persistence and a results‑focused mindset.
• As a global company with employees and clients outside of Quebec, fluency in English as a working language is required for this position.

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!

Be a changemaker

You’ll enjoy:

• 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 Mac‑book.
• 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.

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 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 these 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.