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.
- Solid 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.
- Strong analytical mindset with expertise in program metrics, dashboards, capacity planning, and executive reporting.
- Experience mentoring TPMs and driving continuous process improvements across organizations.

📌 Technical Program Manager (Toronto)
🏢 Flexton
📍 Toronto