Top Tech Jobs & Startup Jobs in Toronto

Own the architecture and technical strategy for Square’s go-to-market technology stack. Build and operate production AI agents, automated workflows, and integrations that improve sales productivity. Lead complex technical initiatives across teams, establish reliable and secure AI evaluation practices, make build-versus-buy decisions, and partner with Sales, Product, Data, and Engineering leaders. Mentor engineers, guide design and implementation, and use data and feedback to improve system adoption and business impact.

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.

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.

Own the architecture and technical strategy for Square’s go-to-market systems. Build and operate production AI agents, automated workflows, and integrations that improve sales productivity. Lead complex initiatives through architecture, implementation, testing, deployment, and operations while establishing AI evaluation, observability, security, reliability, and human-oversight practices. Partner with Sales, Product, Data, and Engineering leaders to translate business needs into scalable solutions, make build-versus-buy decisions, mentor engineers, and improve business impact through data and user feedback.

Own a Santa Clara territory through primarily in-person field sales. Generate pipeline via business visits, networking, events, partnerships, and cold outreach; run full-cycle sales from prospecting through demos and closing; build seller relationships; support onboarding; maintain Salesforce activity and forecasts; master restaurant, retail, and service verticals; and consistently exceed quota.

Own and grow an Oakland territory through primarily in-person field sales. Generate pipeline via business visits, cold outreach, events, networking, and partnerships; conduct demos; sell Square’s software, hardware, and financial solutions; and close full-cycle deals. Build relationships with local businesses, support onboarding, develop referrals, manage pipeline and forecasting in Salesforce, and consistently exceed quota across restaurant, retail, and services verticals.

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.