Top Tech Jobs & Startup Jobs in Toronto

Own the full outbound sales cycle for mid-market merchants, from prospecting and pipeline development through discovery, product demonstrations, negotiation, and close. Build net-new business through strategic outreach, sell multi-product solutions, manage complex multi-stakeholder deals, forecast accurately in Salesforce, and consistently exceed revenue targets. Collaborate with business development, product, marketing, implementation, and operations teams while serving as a consultative advisor to merchants.

Develop data science solutions for payments across Square and Cash App. Build AI-powered tools, ETL pipelines, dashboards, machine learning models, experiments, and cloud data systems. Partner with Product, Engineering, Finance, and Operations to improve payment success, cost efficiency, risk mitigation, and decision-making. Translate business needs into practical solutions, research questions independently, and operationalize data processes and infrastructure.

Design, build, scale, and operate high-volume payment APIs and distributed systems serving global traffic. Lead complex engineering projects from requirements through production, improve reliability, performance, observability, fault tolerance, and security, and participate in on-call and incident response. Collaborate across product and engineering teams, use AI-assisted development tools responsibly, and mentor engineers through technical reviews and documentation.

Leads Square’s US Business Development Representative organization through managers and frontline teams. Owns pipeline generation strategy, operating cadence, performance management, forecasting, capacity planning, outbound execution, and sales technology improvements. Coaches managers, develops BDR talent, hires and retains staff, and partners with Sales, Marketing, Revenue Operations, Enablement, Analytics, and Strategy to improve funnel conversion and revenue contribution. Uses data, automation, AI, and prospecting tools to improve productivity and scale successful programs.

Own Square Hardware sales and revenue across major U.S. retail partners. Build and scale retail partnership strategies, manage existing retailer and distributor relationships, source and negotiate new partnerships, lead cross-functional launches and forecasting, and manage retail marketing budgets through test-and-learn investments.

Lead global ecosystem partnerships for Block’s Afterpay, Cash App, and Square products. Develop partner strategies, build executive relationships, design scalable partnership programs, commercialize B2B and B2B2C payment products, negotiate agreements, and expand distribution through third-party platforms. Collaborate with Product, Engineering, Sales, Marketing, Finance, Compliance, and Legal teams to maximize partner performance and commercial growth.

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.