Territory Account Executive - Winnipeg

Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn't work together.

So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage inventory, offer buy now, pay later functionality, book appointments, engage loyal buyers, and hire and pay staff. Across it all, we've embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale.

Today, we are a partner to sellers of all sizes – large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We're building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.

The Role

Location: Winnipeg

At Square, we're re-imagining how small and midsize businesses grow. As a Sales Account Executive on our Outbound Team, you'll bring Square's ecosystem to new sellers across diverse industries by building, shaping, and closing your own pipeline. You'll run sophisticated, multi-product deals from the first touch to final close — blending hunter instincts, consultative depth, and strategic execution.

If you're an experienced closer who thrives in outbound environments, loves solving meaningful business challenges, and consistently delivers against ambitious targets — this is your role.

You Will

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  Own the full outbound sales cycle — from prospecting to negotiation to close — with SMB and mid-market merchants.



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  Build and manage a high-quality pipeline through cold outreach, social selling, targeted campaigns, and creative outbound strategies.



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  Develop multi-product solutions across Square's ecosystem and tailor them to each merchant's unique needs.



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  Conduct high-impact discovery, demos, and negotiations with decisiveness across multi-stakeholder deals.



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  Act as a consultant and trusted advisor — seamlessly flexing across BDR, AE, and AM responsibilities when needed.



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  Collaborate cross-functionally with Product, Marketing, Implementation, and Operations to deliver cohesive solutions.



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  Maintain disciplined pipeline management and forecasting accuracy in Salesforce.



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  Consistently hit and exceed revenue goals — monthly and quarterly.

You Have

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  3+ years of full-cycle B2B sales experience with consistent quota achievement.



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  Proven success in outbound prospecting and net-new business creation (SaaS or fintech preferred).



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  Experience closing complex, multi-threaded deals with longer sales cycles.



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  Ability to build pipeline from scratch using targeted, strategic outreach.



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  Exceptional communication, presentation, and negotiation skills across phone, video, and written channels.



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  Strong consultative selling skills — diagnose business challenges and map tailored solutions.



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  A hunter's mindset — resilient, creative, and driven to win.



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  Ability to work independently while contributing to a team-first environment.



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  Advanced proficiency with Salesforce and modern sales tools.

Block takes a market-based approach to pay, and pay may vary depending on your location. U.S. locations are categorized into one of four zones based on a cost of labor index for that geographic area. The successful candidate's starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. These ranges may be modified in the future. To find a location's zone designation, please refer to this resource . If a location of interest is not listed, please speak with a recruiter for additional information.