Top Tech Jobs & Startup Jobs in Toronto

Leads strategic pricing and monetization across sales-driven channels, managing pricing partners and advising on complex commercial deals. Develops pricing frameworks, approval processes, deal governance, and scalable tools using automation, AI, and data. Partners with Sales, Product, Engineering, Legal, Risk, and Revenue Operations to improve deal economics, profitability, pricing performance, packaging, and portfolio-level monetization strategy.

Develop data tools, AI automations, ETL pipelines, dashboards, and machine learning models for payments. Analyze experiments, optimize payment performance and costs, mitigate risk, maintain data systems and cloud infrastructure, and translate business needs into actionable solutions while partnering with Product, Engineering, Finance, and Operations.

Own the full outbound sales cycle for mid-market merchants, including prospecting, pipeline development, discovery, demonstrations, negotiation, and closing complex multi-product deals. Build net-new business through strategic outreach, tailor Square solutions to merchant needs, collaborate cross-functionally, maintain accurate Salesforce forecasts, and consistently achieve revenue targets.

Build privacy-focused services and infrastructure that support consumer privacy rights across Block. Collaborate with engineering, security, platform, and legal teams to embed privacy solutions, define future privacy technology, mentor engineers, review implementations, and maintain monitoring and system stability. The role involves developing scalable, testable software and creating architectures and processes addressing data governance, data flows, access control, security, and privacy risks.

Leads strategic finance for Commerce go-to-market, partnering with revenue leaders on planning, forecasting, performance management, investment analysis, and commercial strategy. Builds driver-based financial models linking sales, marketing, pricing, adoption, transactions, and retention to outcomes. Evaluates investments using scenario and ROI analysis, prepares executive materials, and manages finance team members.

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

Leads Square’s US BDR organization through managers and frontline teams, owning pipeline generation strategy, forecasting, performance management, coaching, hiring, and talent development. Partners with Sales, Marketing, Revenue Operations, Enablement, Analytics, and Strategy to improve prospecting, lead quality, funnel conversion, tooling, and revenue contribution. Uses metrics, automation, AI, and sales technology to scale outbound motions and build a predictable, high-performing business development organization.

Own IT internal audit projects and portions of the SOX program, including ITGC and ITAC testing, risk assessment, controls evaluation, remediation, and audit reporting. Partner with audit, finance, engineering, process owners, external auditors, and co-sourcing partners. Help establish an AI audit methodology and implement AI-enabled audit efficiencies while maintaining quality, independence, and reliability.

Own end-to-end analytics engineering for AI and developer experience data. Instrument telemetry, build governed production pipelines, define trusted metrics, and create executive-facing dashboards and analyses. Partner with data engineering, AI, and data science teams to improve data quality and connect raw signals to decision-making. Present clear recommendations on AI investment, developer productivity, and ROI while using AI coding agents to build and maintain pipelines, dashboards, and analyses.

Own Square Hardware’s US retail channel strategy, sales, revenue, and retailer partnerships. Responsibilities include managing existing relationships, sourcing and negotiating new partnerships, developing go-to-market playbooks, forecasting sell-through, coordinating cross-functional launches, and managing retail marketing budgets. The role requires entrepreneurial execution, analytical decision-making, autonomy, and approximately 20% travel.