Senior Outbound Account Executive - Retail

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 Senior Account Executive, Outbound to join our high performing Retail sales team in North America.This is a hybrid role (3 days / week in our Toronto office) that receives support from our SDR team with expectations of self generating additional leads in order to overachieve on KPIs. AE’s will be generating a pipeline through prospecting, booking meetings and owning the sales processing from initial outreach to demo and close. You’ll be part of an evolving and innovative company that is changing the way business owners and their customers engage with each other in Retail.

What you’ll be doing:

• Pipeline Development & Sales: Leverage a combination of phone, email, and social outreach to generate new business opportunities. Build relationships, initiate conversations, and identify client needs in the retail sector.
• Lead & Manage the Sales Process: Own the sales cycle from initial outreach to closing deals, including leading demo presentations and negotiating contracts. Manage multiple deals simultaneously within Salesforce.
• Team Collaboration: Work closely with the wider sales and marketing teams to achieve collective business goals. Collaborate with leadership on pricing negotiations, optimizing touchpoints, and refining sales strategies.
• Performance & KPI Management: Accurately forecast sales pipeline and meet monthly and quarterly revenue targets. Track and report key sales metrics (e.g., meetings booked, pipeline health, deal progression).
• Market Intelligence: Provide feedback on market trends, customer challenges, and competitor strategies to help shape the company's direction and offerings.

And a little bit of.... 

• Contributing as part of the wider team to achieve organisational objectives even if this means doing things that aren’t strictly within the scope of your role

What you need to bring:

• 3-5 Years Sales Experience: You have at least 3-5 years of proven sales experience in an outbound B2B sales role, ideally within the retail sector or SaaS industry.
• Full-Cycle Sales Expertise: Experience managing all aspects of the sales cycle, from prospecting to closing.
• Track Record of Success: Demonstrated history of consistently hitting or exceeding sales targets.
• Pipeline Forecasting: Experience with forecasting sales and managing KPIs on a daily, weekly, and monthly basis.
• Self-Motivated & Results-Driven: You are a driven and goal-oriented individual with a strong desire to succeed in a high-performance environment.
• As a global company with employees and clients outside of Quebec, fluency in English as a working language is required for this position.

What will help you succeed:

• Professional Communication: Confident in engaging with C-level executives and senior decision-makers.
• Hunter Mentality: You are proactive, comfortable with outbound prospecting, and understand that success comes from volume and persistence.
• Resilience & Positivity: You embrace challenges, learn from rejection, and maintain a positive mindset.
• Growth Mindset: You thrive in an environment where feedback is valued, and you continuously work to improve your skills.
• Team Player: While you drive your own success, you contribute to the collective success of the team with a collaborative mindset.

How you will be measured on KPI’s:

• Revenue Targets: Consistently meet or exceed your monthly and quarterly revenue goals.
• Pipeline Management: Effectively generate, nurture, and close opportunities to achieve your sales objectives.
• Team Contribution: Play an active role in driving the growth of the business, offering valuable market insights and collaborating on key initiatives.

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?

Come live the Lightspeed experience...

• Ability to do your job in a truly flexible hybrid environment (3 days/week in office);
• Genuine career opportunities in a company that’s creating new jobs everyday;
• Work in a team big enough for growth but lean enough to make a real impact.

… and enjoy a range of benefits that’ll keep you happy, healthy and (not) hungry:

• Lightspeed RSU program (we are all owners)
• Unlimited paid time off policy
• Flexible working policy
• Health insurance
• Health and wellness benefits
• Possibility for transit fees to be covered
• Paid leave assistance for new parents
• Linkedin learning
• Volunteer day

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 $62,000 - $104,000 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.Please note that this compensation information is solely for candidates hired to perform work within Ontario and reflects the amount Lightspeed is willing to pay at the time of this posting. 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