Senior Program Manager

Accountabilities:: Own program management for complex, multi-team software initiatives, coordinating execution across engineering, product, design, QA, platform, and operations throughout the software development lifecycle. Translate ambiguous, cross-functional challenges into clear program plans with milestones, owners, dependencies, and delivery expectations. Establish and evolve agile execution frameworks, including ceremonies, artifacts, governance cadences, and processes, while contributing improvements to broader PMO standards. Provide senior-leadership-ready status reporting, proactively identify and mitigate risks, and manage changes to scope, timelines, and priorities. Contribute to PMO governance through metrics definition, process standardization, adherence tracking, and continuous improvement. Design and deploy multi-step AI-powered workflows that automate PMO coordination across tools and data sources, creating reusable systems rather than one-off solutions. Build and maintain libraries of reusable prompts, templates, skills, plugins, and automations for activities such as status reporting, metrics dashboards, and roadmap development. Establish quality criteria and validation processes for AI-assisted workflows and maintain accountability for the accuracy and reliability of automated outputs. Mentor and coach program and technical program managers on program management practices, organizational priorities, and AI fluency. Maintain reliable program documentation, delivery metrics, and reporting cadences while helping teams anticipate and address upcoming delivery challenges. Requirements: Bachelor’s degree in Computer Science or equivalent practical experience. 15+ years of total industry experience, including 8+ years of technical program management experience leading complex, large-scale programs across multiple teams. Deep understanding of product development lifecycles and technical program management at scale, with a track record of driving initiatives from concept through release. Demonstrated AI fluency, including experience designing and deploying at least one multi-step AI workflow spanning multiple tools or data sources with measurable improvements in time or quality. Hands-on experience creating reusable AI workflows, prompts, skills, or templates and configuring connectors or plugins independently. Experience using AI or scripting to automate program-management workflows, including extracting and analyzing Jira or Confluence data, generating status reports, or developing reusable reporting systems. Ability to define quality criteria, validate AI-generated outputs, and maintain accountability for the accuracy of automated processes. Experience with project management tools such as Atlassian products, Microsoft Project, Smartsheet, or equivalent, along with strong Agile/Scrum knowledge and familiarity with SAFe. Experience collaborating with product management, design and UX, customer success, customer support, sales, marketing, legal, and other cross-functional teams. Experience with program and project governance, including budgeting, vendor management, compliance, and performance metrics. Professional certifications such as PMP, ACP, or CSM are a plus. Experience with fintech platforms, AWS, Docker, and Kubernetes is advantageous. Self-driven, adaptable, and comfortable mentoring peers and collaborating across geographies and time zones. Benefits: Canadian base salary of $120,000–$150,000 CAD. Equity opportunities as part of the overall compensation package. Health, dental, and vision coverage for employees and their families. Life insurance and mental wellness coverage. Fertility and growing-family support. Flex Time Off in addition to company-paid holidays. Paid family, medical, and bereavement leave. Retirement savings plans. Allowance to customize your home office and technology setup. Annual professional development stipend..