Top Tech Jobs & Startup Jobs in Toronto

Field-driven territory sales role responsible for full-cycle, self-sourced selling across Square's products. Spend ~80% of time visiting 50-60 targeted businesses weekly, run demos, build pipeline via door-to-door outreach and partnerships, manage Salesforce pipeline, and consistently exceed quota while supporting fast onboarding and cross-functional collaboration.

Lead and develop a remote team of Account Executives to drive revenue growth. Hire, train, coach, and manage KPIs, forecasting, and pipeline. Build repeatable sales processes, run pipeline and forecast reviews, collaborate cross-functionally, use customer feedback to improve products, and evolve sales strategy to increase revenue and customer success.

Own the full outbound sales cycle for mid-market merchants: prospect, build pipeline, demo, negotiate, and close multi-product deals. Drive net-new logo acquisition, forecast in Salesforce, collaborate cross-functionally, and consistently exceed revenue targets.

Own full B2B sales cycle for mid-market merchants: prospect, build and manage pipeline, demo multiproduct Square solutions, negotiate complex contracts, collaborate cross-functionally, maintain Salesforce forecasts, and consistently exceed revenue targets.

Manage the full sales cycle for SMB merchants: convert inbound leads, proactively prospect to build pipeline, close high-volume short-cycle deals, deliver consultative solutions, collaborate cross-functionally, and consistently hit monthly and quarterly revenue targets using Salesforce.

Lead and develop a remote team of 8-10 SMB Account Managers to drive upsell, retention, software adoption, and churn reduction. Establish performance expectations, coach managers, run cadences and escalations, partner cross-functionally to improve customer experience, and support OKRs. Travel quarterly for team events or customer meetings.

Own the full sales cycle for SMB merchants in Canada: convert inbound leads, prospect outbound, manage pipeline in Salesforce, collaborate with cross-functional teams, and consistently hit monthly and quarterly revenue targets while improving conversion and deal size.

Own the full outbound mid-market sales cycle: prospect, build pipeline, run discovery and demos, negotiate multi-product deals, and close new logo business while collaborating cross-functionally and maintaining accurate Salesforce forecasts to exceed monthly and quarterly revenue targets.

Lead pricing modeling and experimentation to optimize margin, conversion, and retention. Build elasticity and willingness-to-pay models, design A/B and bandit experiments, develop pricing automation (DealBot) and monitoring for AI-driven rate recommendations, own ETL/analysis/visualization, and partner with Finance, Risk, Product, and GTM teams to operationalize pricing intelligence.

Convert inbound leads and prospect outbound opportunities to close SMB merchants. Own full sales cycle, qualify, demo, and forecast in Salesforce, collaborate cross-functionally, and consistently exceed monthly and quarterly revenue targets.