Top Tech Jobs & Startup Jobs in Toronto

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 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 end-to-end strategy and execution for Tier 1 trade shows and industry events in retail and food & beverage. Own event selection, budget management, ROI tracking, booth design/production, vendor relationships, lead capture processes, cross-functional alignment, and inventory/shipping logistics. Travel to key events (up to 25%) and collaborate with sales, creative, product, and partners to drive qualified leads and showcase Square solutions.

Lead and scale a Product Sales overlay team to drive adoption, expansion, and revenue for strategic products. Own commercial strategy, operating model, go-to-market plays, and cross-functional launch and enablement. Partner with AEs, AMs, Product, RevOps, and Marketing to prioritize opportunities, shape deal strategy, and deliver customer-facing executive engagement to maximize product penetration and outcomes.

Lead global referral and growth partnerships to drive seller acquisition. Define partnership strategy, source and negotiate complex commercial agreements, launch and scale integrations, manage C-level relationships, measure KPIs, and build a high-performing partnerships team across markets.

Lead growth through reseller channel partnerships: recruit, sign, launch, and scale reseller relationships; own deal execution and negotiations; build business cases; collaborate cross-functionally; and be accountable for partner-driven customer acquisition and revenue.

Build and operate ingestion and reconciliation pipelines that match card-network and partner reports against internal transactions. Develop reporting products, produce standardized journals for accounting, support tax and regulatory filing systems, handle sensitive PII for compliance, debug production issues, and collaborate with finance, product, and data teams to automate and scale reconciliation and reporting.

Lead cross-team iOS engineering for Neighborhoods across Cash App and Square: define architecture, stay hands-on with SwiftUI/Workflow codebases, deliver integrated loyalty/ordering features, mentor engineers, and adopt AI-native workflows to accelerate development and quality.

Lead technical direction and architecture for Neighborhoods mobile experiences across Cash App and Square. Drive cross-organizational mobile initiatives, stay hands-on in iOS development, partner with backend/web/Android teams, mentor engineers, and apply AI-assisted workflows to accelerate feature development and quality.

The Senior Manager will define and drive the Services vertical strategy, enhance revenue performance, and ensure product alignment with sales efforts. They'll collaborate across teams, translate insights into actionable guidance, and shape product roadmap decisions, advocating for innovation and measurable impact on revenue.