We are seeking an experienced Technical Program Manager to lead large-scale, cross-functional technology programs within a Payments & Financial Services organization . This role partners closely with Product, Engineering, Business, Design, Marketing, and Operations teams to drive strategic initiatives, align roadmaps, manage dependencies, and ensure successful delivery of business-critical programs.
Key Responsibilities Lead complex, cross-functional technical programs from planning through execution and launch.
Drive annual and quarterly planning, roadmap development, prioritization, capacity planning, and governance.
Coordinate multiple engineering, product, and business workstreams while managing cross-team dependencies.
Identify, track, and mitigate program risks, blockers, and delivery challenges.
Establish operating cadences, governance frameworks, and executive reporting processes.
Prepare executive-ready status reports, dashboards, risk registers, and program updates.
Analyze program metrics, identify delivery risks, and drive data-informed decisions.
Partner with Engineering, Product, Analytics, Operations, Marketing, and other stakeholders to ensure successful execution.
Improve program management processes and leverage AI/GenAI tools to automate planning, documentation, and reporting.
Required Qualifications: Bachelor's degree in Computer Science,



Engineering, Business, or a related field.
7+ years of Technical Program Management experience leading enterprise-scale software programs.
Strong technical background with a solid understanding of software architecture, APIs, distributed systems, cloud technologies, SDLC, Agile, DevOps, CI/CD, and release management.
Experience managing complex cross-functional programs with multiple stakeholders in fast-paced product organizations.
Hands-on experience using AI/GenAI tools such as ChatGPT, Gemini, Claude, NotebookLM, Glean, or similar to improve program delivery.
Strong experience with Jira, Confluence, Airtable, Smartsheet, Google Workspace, and reporting tools such as Tableau, Power BI, or Looker.
Excellent stakeholder management, executive communication, negotiation, and influencing skills.
Proven ability to manage risks, resolve blockers, drive prioritization, and lead teams through ambiguity.
Preferred Skills Experience in Payments, Financial Services, FinTech, eCommerce, or Marketplace platforms.
Robust analytical mindset with expertise in program metrics, dashboards, capacity planning, and executive reporting.
Experience mentoring TPMs and driving continuous process improvements across organizations.

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📌 Technical Program Manager (Ontario)
🏢 Flexton
📍 Ontario