Top Tech Jobs & Startup Jobs in Toronto

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.

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.

The Strategic Account Manager will manage a portfolio of mid-market sellers, negotiating contracts, identifying growth opportunities, and ensuring seamless client service alongside cross-functional teams.