Senior Outbound Account Executive - Retail

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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: Effec