Top Tech Jobs & Startup Jobs in Montreal

Build and operate a scalable data platform supporting warehousing, orchestration, business intelligence, governance, and agentic workflows. Develop Python services, Terraform infrastructure, and developer tools for petabyte-scale data. Partner with data practitioners and product teams, establish security and reliability patterns, set technical direction, improve engineering standards, and mentor engineers.

Lead Block’s global Workforce Optimization function across customer-facing and regulated operations. Establish strategy for forecasting, capacity planning, staffing, real-time management, analytics, automation, and vendor governance. Build predictive workforce systems, align operational and financial plans, manage risk and compliance capacity, oversee incidents and escalations, and develop a multidisciplinary global team supporting employees, outsourced partners, and AI systems.

Own global B2B lifecycle and email marketing for Afterpay and Cash App merchants. Develop personalized prospect, onboarding, adoption, retention, churn-prevention, and winback journeys across regions. Lead email testing, segmentation, AI-enabled personalization, product launches, reporting, and cross-functional collaboration with Sales, Product, Content, Partnerships, and Compliance to increase pipeline, transaction volume, engagement, and retention.

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.

Build and scale first-line risk control performance monitoring for financial products. Develop metrics, key risk indicators, statistical baselines, thresholds, automated workflows, and reusable analytical modules. Partner with risk, compliance, product, and engineering teams to improve governance, identify monitoring gaps, evaluate control effectiveness, and support decisions. Lead ambiguous initiatives from definition through adoption while communicating findings, limitations, and recommendations to technical and executive stakeholders.