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Enterprise Account Executive

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Block

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Location:
Canada , Toronto

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Category:
Sales

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Contract Type:
Employment contract

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Salary:

269800.00 - 404600.00 USD / Year
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Job Description:

As an Enterprise Account Executive, you'll be the tip of the spear for Square's most strategic, high-value deals. You'll navigate multi-threaded sales cycles with executive stakeholders involving technical integrations and cross-functional alignment. This is a role for a seasoned enterprise seller who owns the full deal lifecycle — from cold outreach to signed contract — and thrives in the complexity that comes with it. You'll join a high-performing enterprise sales team that is deeply supported and strategically prioritized. Square is making significant investments to bring Square upmarket at scale and enable enterprise sales success. This is a team that operates with rigor, moves with urgency, and takes pride in signing the largest deals for the company.

Job Responsibility:

  • Craft and Lead Deal Strategy: Develop sophisticated, insight-led sales narratives tailored to client business priorities. You will identify the right entry points, mapping stakeholder influence, and building compelling business cases that create clear ROI
  • Own the Full Sales Cycle: Manage your pipeline end-to-end with precision — from prospecting and discovery through negotiation and close — qualifying rigorously and driving momentum at every stage without losing sight of the details
  • Lead Technical, Complex Sales Cycles: Partner closely with Solutions Engineering to scope platform requirements and API integrations. Translate deeply technical concepts into language that resonates with executive decision-makers and know when to bring in the right expert at the right moment
  • Orchestrate Internal Alignment: Quarterback cross-functional stakeholders across Finance, Legal, Risk, Product, Solutions Engineering, and Account Management — proactively surfacing blockers, resolving ambiguity, and ensuring everyone is aligned and moving in the same direction
  • Represent Square at the Highest Level: Represent Square in C-suite meetings, on stage at industry conferences, or in working sessions with a prospect's technical team — with executive presence that is polished, credible, and authentic
  • Build Block's Enterprise Network: Represent Square at industry events, trade shows, and networking functions
  • develop lasting relationships with senior leaders at leading brands and platform partners
  • Be a Multiplier for the Business: Channel the voice of the customer internally to influence product roadmaps and go-to-market strategy
  • apply AI tools to sharpen your research, automate workflows, and increase your overall output

Requirements:

  • 8+ years of enterprise sales experience, with a track record of closing complex, high-value deals with end-to-end ownership
  • Deep experience in technical sales cycles — you're fluent in conversations involving API integrations, custom development, and platform configuration, and you collaborate naturally with Solutions Engineering teams
  • A proven ability to orchestrate multi-stakeholder deals — internally and externally — with exceptional communication, follow-through, and organizational discipline
  • Executive presence that's equally at home on a conference stage, in a C-suite boardroom, or on a discovery call with a technical champion
  • Experience selling a complex ecosystem of SaaS or fintech products, ideally in payments, commerce, or adjacent verticals
  • The ability to operate independently in a fast-paced, ambiguous environment — you don't wait to be told what to do next
  • A talent for translating complexity into clarity — whether that's simplifying a technical integration for a CFO or structuring an ambiguous problem for an internal stakeholder
  • A BA/BS degree or equivalent professional experience
  • Willingness to travel ~40%
What we offer:
  • Remote work
  • medical insurance
  • flexible time off
  • retirement savings plans
  • modern family planning

Additional Information:

Job Posted:
May 03, 2026

Employment Type:
Fulltime
Work Type:
Remote work
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