Top Tech Jobs & Startup Jobs in Toronto

Graduate research internship to own end-to-end research on Customer World Models and proactive intelligence: design representations, develop methods (foundation models, RL, causal reasoning, agentic systems), run experiments, publish, and help ship ML systems that anticipate and act on customer needs.

Owns end-to-end reconciliation and financial reporting across card networks, banks, processors, and internal ledger data. Designs SQL-based reporting, dashboards, exception queues, metrics, controls, and automated solutions; investigates discrepancies, improves data pipelines, supports month-end close and audits, and partners with Finance, Accounting, Treasury, Tax, Compliance, Engineering, and Product. Mentors analysts and drives process improvements, automation, and responsible AI adoption.

The Staff Software Engineer will lead technical strategies for the Cash App Banking team, overseeing architectural decisions, mentoring engineers, and developing financial products that improve customer banking experiences.

Lead Canada compliance for Square and Afterpay: own the annual compliance plan, manage AML/ATF, RPAA, PCI, privacy and consumer protection programs, FINTRAC registration, regulatory engagements, board reporting, issue remediation, and cross-functional initiatives including AI-enabled compliance tooling and training.

Lead product data engineering initiatives by designing data models, owning critical pipelines, building data quality and lineage monitoring, and supporting experimentation and ML-ready datasets. Translate business needs into automated data solutions, maintain pipeline SLAs through on-call support, and develop AI-assisted tools for issue detection and resolution. Collaborate with Product, Engineering, Data Science, Machine Learning, and Applied AI teams across Block’s products.

Leads strategic pricing and monetization across Block’s sales-driven channels. Manages a team supporting complex enterprise deals, develops pricing and approval frameworks, and partners with Sales, Product, Engineering, Legal, Risk, and Revenue Operations. Uses automation, AI, and data to scale Deal Desk capabilities, improve commercial governance, analyze deal economics, and identify broader pricing, packaging, monetization, and portfolio opportunities.

Leads Cash App Investing’s FINRA- and SEC-regulated compliance program, overseeing policies, controls, monitoring, supervisory procedures, regulatory exams, filings, communications review, product compliance, AML partnerships, vendor oversight, governance reporting, and regulator engagement. Advises cross-functional teams on regulated financial products and develops a high-performing compliance organization.

Supports identity and access management, troubleshoots technical issues across Salesforce, Amazon Connect, Okta, and internal systems, and resolves tickets for internal support teams. The role validates system functionality, manages Jira escalations, partners with engineering during incidents, automates workflows, documents solutions, and identifies recurring issues for systemic improvement. It requires strong technical troubleshooting, communication, organization, and the ability to interpret code, logs, and system configurations.

Lead technical direction and hands-on development of Bitcoin and stablecoin iOS products across Cash App, Square, and Bitkey. Own architecture, implementation, testing, service integration, rollout, observability, security, and post-launch improvements. Build foundational systems, mentor engineers, influence cross-team standards, collaborate across platforms, and integrate AI-assisted development tools while maintaining software quality and reliability.

Own activation and habituation goals for Cash App by setting growth strategy, managing the roadmap and experiment backlog, and shipping product, messaging, incentive, and personalization initiatives. Diagnose funnels, run rigorous experiments, size opportunities, and collaborate with Engineering, ML, Design, Analytics, Martech, Creative, and Brand. Drive AI-enabled decisioning and scale successful lifecycle programs across the business.