Top Tech Jobs & Startup Jobs in Toronto

Own commercialization of Block’s emerging AI portfolio from product and pilot stages through scaled enterprise adoption. Develop market strategy, pricing, packaging, partnerships, and routes to market; secure lighthouse customers and strategic partners; design pilots that convert to production relationships; create repeatable sales and partnership processes; and build the commercial organization as product-market fit develops.

Lead commercialization of emerging AI products by winning enterprise customers and strategic partners, structuring pilots, converting engagements into scaled relationships, and owning partnerships from negotiation through launch and optimization. Collaborate closely with Product and Engineering to shape offerings, validate product-market fit, develop pricing and commercial models, and build a scalable go-to-market strategy.

Own the full-cycle sales process for mid-market commerce merchants across Cash App Pay and Afterpay. Responsibilities include prospecting, pipeline generation, discovery, account planning, business-case development, pricing and contract negotiation, cross-functional deal coordination, forecasting, and closing new business. The role requires building executive relationships, managing complex commercial opportunities, delivering revenue targets, representing the company at events, and contributing to sales enablement and process improvement.

Leads ambiguous, high-impact revenue strategy initiatives from analysis through executive recommendation. Responsibilities include sales forecasting, pipeline health measurement, capacity planning, organizational sizing, commercial deal economics, partnership modeling, and building scalable operating processes. The role partners cross-functionally with Sales, Finance, Partnerships, Services, Data, and Systems, influencing outcomes without direct authority.

Lead the architecture and evolution of native iOS foundations supporting seller-facing applications. Identify systemic problems, define platform strategy and standards, build prototypes and reference implementations, lead multi-quarter migrations, and establish practices for quality, testing, observability, release safety, and maintainability. Develop senior engineers and create scalable ownership models across teams.

Build and operate highly reliable card-issuing software and tooling across authorization, clearing, settlement, certification, and network integrations. Serve as a technical expert on card-network specifications, protocols, mandates, and production behavior. Lead complex cross-team engineering work, debug protocol-level issues, influence network requirements, mentor engineers, improve platform reliability, and participate in on-call support for critical financial systems.

Lead global ecosystem partnerships for Block’s Square, Cash App, and Afterpay products. Develop partnership strategies, build executive relationships, design scalable programs, negotiate commercial agreements, and commercialize B2B and B2B2C payment products through third-party platforms. Own partner performance, drive integrations and distribution, and collaborate with Product, Engineering, Sales, Marketing, Finance, Compliance, and Legal teams to maximize growth and reach.

Build and operate GRC data pipelines, integrations, policy-as-code, continuous control monitoring, evidence automation, and agentic AI workflows. Normalize security data from diverse systems, create auditable evaluation harnesses, govern AI systems, and define technical direction across teams. Partner with security governance, compliance, and engineering groups to transform manual governance processes into scalable products.

Lead Block’s global tax planning and controversy agenda, including international and U.S. tax strategy, transfer pricing, M&A taxation, legal-entity structuring, tax audits, examinations, disputes, and transaction negotiations. Advise senior leadership on tax implications, partner with Legal, Treasury, Corporate Development, and finance teams, monitor legislative developments, and ensure tax positions are reflected in reporting and compliance. Build high-performing teams and represent Block before domestic and foreign tax authorities.

Own the architecture and technical strategy for Square’s go-to-market technology stack. Build and operate production AI agents, automated workflows, and integrations that improve sales productivity. Lead complex technical initiatives, establish AI reliability and security guardrails, define evaluation metrics, and guide build-versus-buy decisions. Partner with Sales, Product, Data, and Engineering leaders while mentoring engineers and remaining hands-on across design, implementation, testing, deployment, and operations.