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Manage and grow a book of SMB merchants in Eastern Canada through relationship building, product education, cross-selling, upselling, pipeline management, and collaboration with Sales, Support, and Product teams to improve merchant outcomes and retention.

The Business Development Representative will manage a diverse pipeline, perform outreach through cold calling, and identify business challenges to promote Square's solutions. They will document opportunities and aim to exceed sales quotas, fostering career growth within the organization.

The Enterprise Account Executive leads and manages complex sales cycles for high-value deals, driving strategy and collaboration with technical teams and executives to close contracts successfully.

The role involves selling Square's ecosystem to SMB merchants, overseeing the sales cycle, achieving sales goals, and ensuring successful onboarding with a consultative approach.

Full-cycle, field sales role responsible for building pipeline and closing deals through in-person visits and demos. Own territory execution, forge local partnerships, drive referrals, and maintain CRM discipline to consistently exceed quota.

Lead and develop a remote mid-market sales team of Account Executives to drive revenue growth. Hire, train, coach, and manage KPIs, forecasting, and pipeline. Participate in client meetings, build repeatable sales processes, evolve strategy, and use customer feedback to improve products.

Lead and coach a remote team of Account Executives to meet individual and team sales quotas. Hire, train, and ramp AEs; manage KPIs, forecasting, and pipeline reviews; participate in client meetings and co-sell. Develop repeatable sales processes, evolve strategy, and use customer feedback to improve products.

Lead end-to-end enterprise sales for Square9s upmarket business: craft deal strategy, manage complex technical integrations and multi-stakeholder negotiations, partner with Solutions Engineering, align internal teams, represent the company to executives, and close high-value contracts while influencing product and go-to-market strategy.

Outbound-focused senior account executive responsible for sourcing and closing new restaurant merchant logos. Duties include prospecting, discovery, demos, consultative selling of Square ecosystem, field relationship building, partnering with BD/Product/Marketing, managing the sales cycle and onboarding, and meeting monthly sales KPIs using Salesforce.

Design and own end-to-end product experiences that drive seller onboarding, activation, adoption, and retention across mobile and web. Partner with PMs, engineers, and data science to simplify complexity, iterate quickly, and deliver high-quality, platform-native interfaces while elevating design craft and mentoring others.