Top Sales Jobs in Toronto, ON

Lead and scale Block's Product Sales organization to accelerate adoption of strategic products. Own commercial strategy, operating model, territory planning, forecasting, and performance metrics. Partner with AEs, AMs, Product, Rev Ops, Marketing, and Enablement to drive product adoption, expansion, pricing, launches, and executive customer engagements. Recruit, develop, and coach leaders and specialists while creating repeatable sales plays, enablement programs, and commercialization strategies to meet revenue and adoption goals.

Lead and scale North American SMB sales across BDR, Inbound, and Outbound motions. Build playbooks, processes, and tooling to drive pipeline, forecasting rigor, merchant conversion, and revenue. Hire, coach, and develop managers and reps, partner cross-functionally (Product, Marketing, Finance, Risk, Legal), represent the business to merchants, and deliver merchant feedback internally. Drive OKRs, revenue targets, and a high-performance culture while iterating based on data and business needs.

Lead North American Mid-Market Sales to drive revenue for Cash App and Afterpay. Manage and coach a team of account executives, negotiate complex commercial deals, build cross-functional partnerships, shape go-to-market and portfolio strategy, represent the business to merchants, and advocate merchant feedback internally. Own revenue outcomes, team development, and scalable sales processes.

Lead and develop a remote mid-market sales team of Account Executives to drive revenue. Hire, train, and coach AEs; enforce KPI-driven execution, forecasting, and pipeline management; run pipeline and forecast reviews; evolve sales strategy and processes; participate in client/prospect meetings and use customer feedback to improve products.

Lead Square's global commercial operating system and Deal Desk, operationalizing pricing strategy, building approval workflows and AI-enabled automation, supporting strategic enterprise deals, driving governance, reporting, and seller productivity, and building a high-performing global team to increase deal velocity while protecting profitability.

Lead and coach a remote team of Account Executives to hit individual and team quota. Hire, train, forecast, manage pipeline and KPIs, run regular reviews, participate in client meetings, refine sales strategy, and use customer feedback to improve products and processes.

Lead GTM strategy and revenue operations for global Sales: design segmentation, territory and coverage models, analyze funnel and productivity, run WBR/MBR cadence, lead cross-functional programs, translate goals into technical requirements, and champion AI/automation to improve sales productivity and execution.

Lead and manage enterprise payment partnerships end-to-end: source, negotiate, and close integrations with software platforms; build API expertise; drive go-to-market execution with Sales and Account teams; collaborate cross-functionally (Product, Solutions Engineering, Marketing, Legal); and own partner performance and business outcomes tied to GPV, seller acquisition, and enterprise wins.