Top Tech Jobs & Startup Jobs in Toronto

Generates outbound leads among small and medium-sized businesses through cold calls, personalized email, and prospecting. Builds and maintains a high-volume sales pipeline, meets KPIs, engages prospective and existing accounts, conducts needs analysis, and records activity in Salesforce for handoff to Account Executives.

Own Square’s organic social strategy, audience definition, content calendar, community management, social listening, creator and influencer partnerships, crisis support, and channel performance. Develop and publish content with creative partners, connect social to brand positioning and campaigns, coordinate organic and paid efforts, assess trends, and provide performance insights and recommendations across teams.

Lead technically complex card-acquiring payment projects from design through production. Build and operate highly reliable payment systems, integrations, testing and certification tooling, and shared engineering frameworks. Analyze ISO messages, network mandates, routing, authorization, clearing, settlement, and processing costs. Provide technical direction, mentor engineers, participate in on-call operations, and establish safe AI-assisted engineering practices for critical financial systems.

Operate and mature Block’s global business resilience program across business continuity, disaster recovery, crisis management, operational resilience, third-party resilience, testing, reporting, and regulatory support. Identify risks, maintain recovery plans, coordinate exercises, track remediation, assess third parties, communicate resilience posture to leadership and Boards, and improve workflows through AI, automation, dashboards, templates, and self-service tools.

Lead product data engineering across architecture, data modeling, pipelines, monitoring, lineage, and data quality. Build reliable analytical datasets, support experimentation and machine learning use cases, and resolve business-critical pipeline issues. Partner with product and engineering stakeholders to translate business needs into automated data solutions. The role requires ownership of end-to-end data engineering projects, on-call participation, and development of AI-assisted monitoring and automation.

Leads creative and content strategy for growth marketing portfolios, connecting audience insights, product messaging, paid and unpaid channels, landing pages, and business outcomes. Owns messaging frameworks, testing roadmaps, creative development, performance reviews, experimentation, and optimization. Uses AI-enabled tools and cross-functional influence to scale winning concepts, improve conversion, and drive acquisition and consideration.

Leads the compliance program for Cash App Investing’s FINRA- and SEC-regulated broker-dealer business. Responsibilities include developing policies and controls, overseeing supervisory procedures, regulatory filings, communications review, complaints, examinations, remediation, AML coordination, vendor oversight, governance reporting, and regulator engagement. The role advises product, engineering, legal, marketing, and operations teams while building and managing a high-performing compliance organization.

Lead the technical direction and delivery of Bitcoin and stablecoin experiences for iOS across Cash App, Square, and Bitkey. Build and ship complex features end to end, establish architecture and shared systems, integrate backend services, improve testing and release safety, and mentor engineers. Collaborate across product, design, Android, web, and backend teams while applying AI-assisted development practices and contributing to secure, reliable customer experiences.

Leads the global operating system for seller onboarding, including KPI frameworks, business reviews, reporting, capacity planning, workforce modeling, financial support, process standardization, and continuous improvement. Partners cross-functionally to translate strategy into measurable plans and drives AI-enabled workflow adoption, training, and performance improvements across regions and delivery models.

Own activation and habituation growth for Cash App by setting strategy, managing the roadmap and experiment backlog, and shipping product, messaging, incentive, and personalization initiatives. Partner directly with Engineering, ML, Design, Analytics, and Marketing to diagnose funnels, run rigorous experiments, improve retention, and scale successful lifecycle programs. The role requires strong data analysis, CRM expertise, AI fluency, and end-to-end ownership of measurable growth outcomes.