Top Tech Jobs & Startup Jobs in Toronto

Supports global sales enablement and everboarding by planning, maintaining, and facilitating ongoing learning content. Coordinates stakeholders, manages knowledge resources, communications, training assets, and localized Canada enablement. Tracks adoption, knowledge retention, and performance impact while promoting playbooks, FAQs, internal wikis, and LMS content. Requires sales enablement experience, adult learning knowledge, strong communication, stakeholder management, and organizational skills.

Conduct outbound prospecting through cold calls, email, and social selling to identify qualified merchant opportunities for Square. Manage and prioritize a diverse business pipeline, understand merchant needs, promote Square solutions, meet or exceed monthly quotas, and pass qualified leads to Account Executives. The role emphasizes data-driven sales, bilingual French and English communication, professional development, and career growth within sales.

Graduate research co-op focused on building Customer World Models and proactive intelligence: designing representation learning, foundation-model, reinforcement learning, and agentic systems; running experiments, publishing, and deploying research into production to improve long-horizon decision-making and customer-facing automation.

Own the full outbound sales cycle for mid-market merchants, from prospecting and pipeline development through discovery, negotiation, and close. Sell tailored, multi-product Square solutions in complex, multi-stakeholder deals, maintain accurate Salesforce forecasts, collaborate cross-functionally, and consistently exceed revenue targets.

Own the architecture and technical strategy for Square’s go-to-market technology stack. Build and operate production AI agents, automated workflows, and scalable integrations that improve sales productivity. Lead complex technical initiatives across teams, establish AI reliability and security guardrails, define evaluations and success metrics, and guide build-versus-buy decisions. Remain hands-on across prototyping, implementation, testing, deployment, and operations while mentoring engineers and influencing senior business and technical stakeholders.

Own end-to-end reconciliation and reporting for card networks, banks, processors, and internal ledger data. Build SQL-based reporting, dashboards, exception queues, metrics, controls, and automated solutions; investigate discrepancies, improve data quality, support month-end close and audits, and partner with Engineering, Product, Accounting, Treasury, Tax, and Compliance. The role also defines requirements and test plans, maintains data pipelines, mentors analysts, and drives automation across payment settlement and money-movement processes.

As a Staff Software Engineer on the Cash App Banking team, you will lead technical strategy, collaborate on decisions, manage large features, and mentor other engineers to enhance their skills in creating innovative banking solutions.

Own full outbound mid-market sales cycle: prospect, build pipeline, demo, negotiate, and close multi-product deals. Drive net-new logo acquisition, meet revenue targets, collaborate cross-functionally, and maintain accurate forecasting in Salesforce while acting as a trusted consultant to merchants.

Full-cycle SMB sales role converting inbound leads and generating outbound pipeline. Manage high-volume, short-cycle deals, forecast in Salesforce, collaborate cross-functionally, exceed monthly/quarterly revenue goals, and sell bilingually in French and English.

Responsible for full-cycle B2B sales to mid-market merchants: build and manage pipeline, prospect, demo multi-product Square solutions, negotiate complex contracts, collaborate cross-functionally, maintain accurate Salesforce forecasts, and consistently hit monthly and quarterly revenue targets.