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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

Please note this role is based in British Columbia or Alberta.

Lightspeed is looking for a Manager, Outbound Sales to join our growing North American team. The Manager, Outbound Sales will manage a team supporting the West Coast Territory. In this role, you will own a defined segment of outbound sales, leading a team of Account Executives and driving new customer acquisition across a targeted account base. Lightspeed's Outbound team is in hyper-growth mode — our process has been refined and optimized, and now is the time to scale our reach with proven leaders at the helm.

What you’ll be doing:

Own Your Segment

Lead and manage a team of Account Executives responsible for the full sales cycle within a defined segment of North American accounts

Own segment-level pipeline, forecast accuracy, and monthly/quarterly MRR targets — taking full accountability from top-of-funnel through close

Manage overall pipeline health and drive consistent execution against activity, conversion, and revenue KPIs

Collaborate with SDR leadership to ensure a smooth, high-quality lead-to-deal handover process

Develop Your Team

Hire, coach, and develop a high-performing team of Account Executives

Partner with enablement teams to design and deliver onboarding programs for new hires, ensuring reps are ramped and productive as quickly as possible

Drive ongoing skill development through rolling coaching, call reviews, pipeline inspection, and structured feedback loops





Identify individual performance gaps and implement targeted development plans to increase team output and rep tenure

Optimize the Motion

Refine and optimize current sales processes, including all tools used to connect, demo, and close new customers

Work cross-functionally with Sales Ops, Marketing, Enablement, and Product to remove roadblocks, improve tooling, and streamline workflows

Collaborate with regional and functional leaders on developing and executing the outbound strategy playbook

Identify the best tools for list creation, outbound messaging, and deal execution

And a little bit of…

Analyze sales forecasts, call volume, and pipeline health across the team and at the individual rep level

Create recent strategies to grow revenue streams and expand the team’s addressable market

Ensure clear communication and handoff processes across the broader sales organization

How you’ll know you’re winning:

Your team consistently meets or exceeds Net New MRR targets

New hires ramp on schedule and hit productivity benchmarks within expected timelines

Forecast accuracy is tight — projected scenarios reflect reality

Average deal MRR trends upward over time as segment targeting sharpens

Cross-functional partners consider you a go-to for process improvement and execution clarity

What you bring:





Minimum 2 years of experience managing Account Executives in an outbound or full-cycle sales environment

Demonstrated ability to own a segment or territory from pipeline generation through close — with a strong sense of personal accountability for outcomes

Experience working cross-functionally to identify and resolve process gaps, improve tooling, and align stakeholders

Proven ability to onboard, coach, and develop sales reps at multiple stages — new hire, developing, and high performer

Proficiency with Salesforce, Outreach, or comparable sales engagement platforms

Tech-savvy, with the ability to help team members who are less so

Entrepreneurial and agile mindset with a bias toward action and comfort with ambiguity

Experience with Retail or Hospitality point-of-sale systems is an asset

Proficiency in English

Be a changemaker

You'll enjoy:

A adaptable work setting 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

📌 Manager, Outbound Account Executive (Winnipeg)
🏢 Lightspeed Commerce
📍 Winnipeg