Top Tech Jobs & Startup Jobs in Toronto

Own the full enterprise sales cycle for Block’s commerce and payments portfolio, from prospecting and account strategy through negotiation, contracting, launch, and expansion. Build executive relationships with global brands, develop commercial strategies, negotiate complex agreements, coordinate cross-functional teams, and deliver revenue targets. Translate market and customer insights into product and go-to-market feedback while managing strategic pipelines and opportunities.

Build infrastructure and tooling for AI evaluation, including distributed execution, task-set validation, graders, human-review calibration, statistical reporting, online feedback loops, and offline-to-online analysis. Partner with product, engineering, data, and ML teams to create reliable evaluation workflows that support faster, statistically sound AI product decisions.

Graduate research interns will own end-to-end projects to build customer world models and proactive intelligence: developing representation learning, foundation model, RL/agentic methods, evaluation frameworks, and shipping research into production to improve customer decision-making.

Provides embedded compliance guidance for Square product teams, leading product compliance reviews, risk assessments, control evaluations, testing, monitoring, issues management, audits, regulatory change management, and remediation. Partners with Product, Engineering, Design, Legal, Risk, and international teams to translate regulations into practical controls, maintain compliance inventories, manage examinations, and report compliance metrics.

Supports the Chief Compliance Officer in building and administering a federally chartered trust bank’s compliance management system and BSA/AML program. Responsibilities include AML controls, CDD/EDD, transaction monitoring, SAR workflows, OFAC sanctions, Travel Rule compliance, blockchain analytics, compliance testing, issue remediation, regulatory change management, Board reporting, and OCC examination readiness. The role focuses on digital asset custody and fiduciary services while maintaining an independent compliance function.

Leads a team of Product Sales Specialists responsible for product adoption, cross-sell, expansion, pipeline, and revenue outcomes. Coaches consultative selling, manages forecasting and performance, develops scalable sales plays, and partners with Account Executives, Account Managers, Product, Marketing, Operations, Data Science, and Enablement. The role also engages in strategic seller opportunities, improves product expertise across sales teams, and builds repeatable commercial motions for Square’s products.

Build and operate database and storage platform software, including services, APIs, developer tools, migrations, and lifecycle automation. Solve database scaling, performance, reliability, and availability problems across distributed systems, cloud infrastructure, and backend services. Partner with engineering teams on schemas and queries, lead technical projects, modernize platforms, participate in incident response, and use AI-assisted tools in development.

Build and operate full-stack compliance platforms for transaction search, entity labeling, ingestion, and workflow automation. Responsibilities include designing microservices and event-driven systems, writing tested code, improving sensitive financial data quality, building self-service tools and high-volume pipelines, partnering with Compliance and Risk teams, and participating in on-call operations. The role also involves using AI-powered development tools, reviewing code, and supporting engineering standards.

Drive revenue by acquiring and expanding relationships with mid-size and high-growth brands. Lead commercial negotiations, develop deal strategies, manage sales pipelines and forecasts, close new business, and communicate Block’s payments value proposition to senior decision-makers. Build executive relationships and collaborate with Marketing, Finance, Product, Risk, Legal, Operations, and Customer Service teams to execute commercial and product initiatives.

Lead pricing modeling and experimentation to optimize margin, conversion, and retention. Build elasticity and willingness-to-pay models, run causal and bandit experiments, decompose merchant economics, and develop agentic deal tooling. Own end-to-end data pipelines, ETL, monitoring, and visualization. Evaluate AI systems for accuracy, bias, and drift, and partner with cross-functional teams to translate results into pricing strategy and automation.