Top Tech Jobs & Startup Jobs in Toronto

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.

Lead and build Square's global commercial operating system, owning Deal Desk, pricing operations, strategic deal support, and commercial governance. Drive pricing execution, approval workflows, AI-enabled automation, reporting, and cross-functional alignment to increase deal velocity, consistency, and profitability while managing a global team.

Lead vision-heavy product design for Square Point of Sale: craft visual and interaction designs, build prototypes, collaborate with product and engineering, integrate AI-driven experiences, and drive projects from concept through shipped product while raising design standards and systems thinking.

The Business Development Rep Associate will drive sales efforts by reaching out to prospective sellers, promoting Square's value, and managing a diverse business pipeline. Success will lead to growth opportunities within the sales organization. Candidates need to possess excellent sales instincts and a desire to grow in a sales career.

Lead GTM strategy and operations for Global Account Management to improve retention, reduce churn, and drive expansion. Build coverage models, book construction, KPIs, dashboards, and operational cadence. Automate workflows and AI-driven experiments across CRM and GTM tools. Partner cross-functionally with Data Science, Product, Engineering, Finance, and AM to translate strategy into scalable programs, technical requirements, and measurable impact.

Own and grow enterprise payment partnerships by sourcing, negotiating, and closing integrations with software platforms. Drive go-to-market execution with Sales and Account teams, develop API expertise, collaborate cross-functionally, and track partner performance and business outcomes tied to GPV, seller acquisition, and enterprise wins.

Lead GTM strategy and operations for Global Sales: design segmentation, territory and coverage models, build data-driven investment cases, analyze funnel performance, own WBR/MBR cadence and dashboards, run cross-functional projects from PRD to launch, and champion AI and automation to increase sales productivity.

Lead Square-wide Trust strategy across Risk and Identity, owning high-stakes Trust bets while coaching senior PMs. Drive product for Identity Verification, Access, Disputes, and Controls; optimize seller experience, risk loss, and ecosystem health. Operate AI-native, engage regulators and partners, and coordinate Product, Engineering, Compliance, Legal, and Operations to deliver Trust and Safety initiatives.