Top Tech Jobs & Startup Jobs in Montreal

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.

Build and operate Block’s data platform, including warehousing, orchestration, business intelligence, governance, and agentic workflows. Develop reliable Python services, developer tools, and Terraform infrastructure for petabyte-scale data. Partner with data practitioners and product teams, establish engineering standards, provide technical direction, and mentor engineers while ensuring security, reliability, observability, usability, and data governance.

Own and scale enterprise compensation programs, including salary structures, equity, geo-pay, promotions, focal cycles, and incentives. Design compensation governance, policy guardrails, delegation frameworks, automated workflows, AI-assisted self-service tools, and centralized reporting. Advise senior leaders on talent-market positioning, pay equity, and organizational design while partnering with Compensation Operations, data, tooling, and peer program leads.

Leads Legal Innovation & Operations strategy, including legal technology roadmaps, systems optimization, automation and AI initiatives. Oversees CLM, eBilling, knowledge management, and workflow platforms; manages budgets, vendors, and third-party spend; and delivers cross-functional projects with Legal, IT, Finance, Policy, and business teams. The role translates business needs into technology solutions and drives operational excellence through process improvement and data-driven insights.

Lead quota, capacity, and headcount planning across Block’s commercial sales organizations. Build scalable planning methodologies, systems, data, governance, and processes; own quota-setting and hiring models; run scenario analyses; advise Sales and Finance executives; align compensation, recruiting, strategy, and operations; and establish decision rights and operating rhythms for commercial growth planning.

Leads sales compensation operations, including quota assignment, crediting, commission calculations, data pipelines, audits, governance, and payouts. Manages and develops an operations team while partnering with Sales, Finance, Revenue Operations, and senior leadership. Oversees Pigment and Salesforce administration, improves automation and data integrity, resolves exceptions, delivers operational reporting, and ensures compensation plans are executed accurately, transparently, and on schedule.

Build and manage a global Afterpay and Cash App sales enablement and training strategy across North America, the UK, and APAC. Own the internal content platform, facilitate training, communicate product and business updates, collaborate with revenue and GTM leaders, and use AI to scale learning programs. Measure program impact on sales performance while adapting enablement initiatives to regional needs.

Own complex Banking design initiatives from exploration through launch, including zero-to-one financial products and improvements to existing experiences. Set the quality bar for interaction, visual, and systems design while translating financial and regulatory complexity into clear, trustworthy experiences. Partner with Product, Engineering, Risk, Compliance, and Research; prototype with AI and emerging tools; shape product vision and design systems; and mentor designers through critique and hands-on example.

Own and grow a Santa Clara sales territory through primarily in-person execution. Generate leads via door-to-door outreach, events, networking, and partnerships; conduct product demonstrations; close full-cycle deals; build relationships with local businesses; and sell Square’s software, hardware, and financial solutions. Maintain Salesforce pipeline discipline, forecast accurately, exceed quota, and support successful seller onboarding.

Own a local territory for Square, spending approximately 80% of the week in the field conducting business visits, generating leads, delivering demos, and closing full-cycle sales. Build partnerships, referrals, and pipeline through community outreach and networking. Advise restaurants, retailers, and service businesses on Square’s solutions, manage opportunities and forecasts in Salesforce, support onboarding, and consistently exceed sales quotas.