Top Tech Jobs & Startup Jobs in Toronto

Manage the full sales cycle for SMB merchants: convert inbound leads, prospect to build pipeline, forecast in Salesforce, collaborate cross-functionally, provide consultative solutions, and consistently meet or exceed monthly and quarterly revenue targets. Bilingual (French/English) role with high activity volume and short sales cycles.

Lead Canada compliance for Square and Afterpay: own annual compliance plan, manage AML/ATF, RPAA, PCI, consumer protection and privacy programs, drive regulatory engagements, board reporting, issue remediation, and build AI-enabled compliance solutions across functions.

Develop and manage Square’s always-on B2B content engine across social, thought leadership, customer stories, partner content, and industry narratives. Build content calendars, formats, briefs, campaigns, and AI-assisted workflows; collaborate with marketing, sales, creative, communications, and external partners; manage production through launch; and use performance insights to optimize content and distribution.

Build and maintain network edge security systems that improve API security posture, detect and mitigate abusive traffic, and respond to emerging threats. Responsibilities include developing streaming analytics pipelines, integrating CDN and security vendors, managing production systems, contributing to machine learning models, and implementing AI-driven traffic classification. The role requires software or security engineering experience, expertise in Java, Kotlin, TypeScript, Python, SQL, Spark, CDN platforms, and AWS.

Leads and grows an engineering team building financial and supply chain platforms, including agentic workflow automation, reporting, forecasting, tax, compliance, and operational systems. Sets technical direction, architecture, roadmap, and delivery practices while partnering with Finance, Accounting, Tax, Compliance, Product, and Operations. Ensures reliability, security, scalability, testing, observability, and operational excellence, while developing engineers, future leaders, and a healthy engineering culture.

Manage seller onboarding and implementation from discovery through go-live, guiding merchants through product setup, training, hardware installation, data migration, and operational configuration. Coordinate with Sales, Account Management, Customer Success, Engineering, and Product to resolve obstacles and accelerate activation. Lead multiple complex merchant projects, create training materials, track feature requests, and support scalable onboarding strategies. The role requires occasional onsite work and bilingual English-Spanish communication.

Manage a portfolio of mid-market sellers, expanding use cases and technical solutions, negotiating contracts, and providing exceptional client service.

Leads international seller onboarding operations across Europe, the UK, Australia, and APAC. Owns regional execution, staffing, vendor performance, market launches, localization, service levels, operational metrics, cost efficiency, and workflow improvements. Partners with Sales, Product, Finance, Legal, Compliance, and go-to-market teams while developing regional leaders and aligning local operating models with global standards. The role also uses AI to improve seller outcomes and internal workflows.

Leads Sales Development across North America and the UK, owning top-of-funnel pipeline performance, team integration, reporting, targeting, conversion, and revenue contribution. Builds scalable inbound and outbound motions, expands upmarket coverage, develops managers and representatives, and partners with Marketing, Sales, Finance, Risk, Compliance, Product, and Operations. Uses analytics, automation, and AI to improve prospecting and productivity while establishing rigorous planning, coaching, qualification, and performance standards.

Lead North American Mid-Market Sales to drive revenue for Cash App and Afterpay. Manage and coach a team of account executives, negotiate complex commercial deals, build cross-functional partnerships, shape go-to-market and portfolio strategy, represent the business to merchants, and advocate merchant feedback internally. Own revenue outcomes, team development, and scalable sales processes.