LightSpeed Retail

Outbound Account Executive - Toronto

LightSpeed Retail$65K — $109K *
Business Services
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 5-7 years of experience in outbound sales or business development
  • Proven track record of consistently exceeding sales targets
  • Ability to manage and forecast a complex sales pipeline effectively
  • Strong understanding of the sales cycle from first touch to close
  • Experience in leading consultative discovery sessions and product demos
  • Self-motivated, proactive in creating sales momentum
  • Familiarity with Salesforce or similar CRM software (preferred)

Responsibilities

  • Own and manage your sales pipeline from outreach to close
  • Develop and execute outbound sales strategies for targeted market segments
  • Lead impactful discovery calls and product demonstrations to understand client needs
  • Maintain accurate forecasts and meet monthly and quarterly sales targets
  • Qualify and prioritize sales opportunities to maximize revenue
  • Collaborate with SDRs to convert leads into sales opportunities
  • Work cross-functionally to refine sales strategies and share insights
  • Negotiate pricing with confidence using structured deal strategies

Benefits

  • Flexible paid time off and remote work policies
  • Equity options to foster ownership in the company
  • Contributions to pension plans for future security
  • Opportunities for professional training and skill development
  • Health and wellness credits to support employee well-being
  • Volunteer time off to engage with and support the community
  • Participation in employee-led initiatives and social committees
  • Computer purchase program for personal tech upgrades
  • Enhanced parental leave to support family growth
Full Job Description
This is a true ownership role. You'll build and close your own pipeline, working a defined market segment with a strong outbound motion. From first touch to close, you're responsible for driving deals forward through structured discovery, tailored demos, and disciplined deal strategy.

You'll be part of a team that treats outbound as a skill, not a volume game- performance comes from understanding the customer, controlling the sales process, and consistently executing at a high level.

This role is hybrid, based out of our Toronto office (on Spadina), with in-office days every Tuesday, Wednesday, and Thursday.

What you'll be doing:
  • Own your pipeline end-to-end - from generating opportunities through targeted outreach to closing and expanding deals within your territory.
  • Drive outbound strategy into defined market segments, leveraging structured cadences while continuously testing and optimizing your approach.
  • Lead high-impact discovery and product demos - running consultative, screen-share sessions that uncover real business challenges and tie directly to value.
  • Manage a complex sales pipeline using Salesforce, maintaining accurate forecasts and consistently delivering against monthly and quarterly targets.
  • Qualify and prioritize opportunities effectively using key criteria such as GTV, business model, and buying timeline to focus on high-value deals.
  • Partner closely with SDRs to convert outbound interest into qualified opportunities and ultimately closed revenue.
  • Collaborate cross-functionally with leadership and peers to refine strategy, share insights, and elevate overall team performance.
  • Navigate pricing and negotiations with confidence, using structured deal strategy to protect value while driving deals forward.
  • Consistently exceed targets, taking ownership of your performance and contributing to broader team success.

What you need to bring:
  • You've built pipeline through an outbound motion and know how to turn cold outreach into real opportunities
  • You understand how to manage and forecast a pipeline, and you consistently hit or exceed your targets
  • You've been a top performer before and can clearly speak to the results behind it
  • You're comfortable owning the full sales cycle from first touch to close
  • You create your own momentum instead of waiting on inbound; you are not an 'order taker'
  • You know how to run strong discovery and guide deals forward with structure and intent
  • You're comfortable being challenged on your deals and can clearly defend your forecast
  • You're motivated to grow your career at Lightspeed Commerce and be part of a high-performance team

Even better if you have, but not necessary:
  • Experience with Salesforce.com
  • Experience with SaaS
  • Retail experience

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

Plus benefits designed to keep you happy, healthy and fulfilled.
  • 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 $65,550 - $109,250 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

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.

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.

About LightSpeed Retail

LightSpeed Retail is a cloud-based point-of-sale and e-commerce software provider for retailers and restaurateurs. The company was founded in 2005 by Dax Dasilva and is headquartered in Montreal, Canada. LightSpeed Retail's platform allows businesses to manage their inventory, process transactions, and analyze sales data. The company's mission is to help businesses grow by providing them with the tools they need to succeed. LightSpeed Retail has raised over $290 million in funding from investors such as Caisse de dépôt et placement du Québec, iNovia Capital, and Accel Partners.
Learn more about LightSpeed Retail
Size
1,000 employees
Market Cap
$18.4 billion
Industry
Founded
2005
5 Year Trend
+48.5%

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