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 and high-stakes cross-functional challenges into structured program plans with clear milestones, owners, dependencies, deliverables, and timelines. Establish and evolve execution frameworks, including Agile/Scrum ceremonies, governance cadences, program artifacts, and operating practices. Identify, monitor, communicate, and mitigate delivery risks while applying disciplined change management when scope, priorities, or timelines shift. Provide clear, reliable, senior-leadership-ready reporting on program health, progress, dependencies, risks, and key decisions. Contribute to PMO-wide governance by improving metrics, standardizing processes, and supporting adherence to established operating practices. Design and deploy multi-step AI-powered workflows that automate recurring program-management activities across tools and data sources. Build reusable prompt libraries, templates, automations, skills, and integrations for activities such as status reporting, metrics analysis, roadmap management, and Jira/Confluence data extraction. Establish quality criteria and validation mechanisms for AI-enabled workflows and maintain accountability for the accuracy and reliability of automated outputs. Share AI-enabled practices across the PMO and act as a resource for improving the team's overall AI fluency. Mentor and coach program and technical program managers on execution practices, organizational priorities, and effective use of AI. Maintain consistent program documentation, delivery metrics, status reporting, and operating cadences. Help anticipate delivery challenges, improve organizational processes, and strengthen program-management practices across the broader organization. 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 programs across multiple teams. Deep understanding of software product development lifecycles and technical program management at scale, with a demonstrated ability to drive initiatives from concept through release. Demonstrated AI fluency at a workflow-orchestration level, including designing and deploying multi-step AI workflows spanning multiple tools or data sources with measurable improvements in time or quality. Hands-on experience automating program-management workflows using AI, scripting, or related technologies, including extracting and analyzing data from tools such as Jira and Confluence. Experience creating reusable prompts, workflow templates, skills, connectors, or plugins that can be adopted by other program and technical program managers. Strong judgment around AI-assisted work, including defining quality criteria, validating outputs, and maintaining accountability for automated results. Experience with project-management platforms such as Atlassian tools, 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 stakeholders. Experience with program and project governance, including budgeting, vendor management, compliance, metrics, and reporting. Strong communication, stakeholder-management, mentoring, and leadership skills across distributed teams and multiple time zones. Self-directed and adaptable, with the ability to navigate ambiguity, prioritize competing demands, and maintain execution discipline. PMP, PMI-ACP, CSM, or similar professional credentials are a plus. Experience with fintech platforms, AWS, Docker, Kubernetes, or other cloud technologies is a plus. Benefits Canadian base salary range of CA$120,000–CA$150,000 , with actual compensation determined by experience, skills, location, and applicable local requirements. Equity opportunity as part of the overall compensation package. Health, dental, and vision coverage for employees and their families. Life insurance. Mental wellness coverage. Fertility and growing-family support. Flexible 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. Remote work environment with collaboration across multiple geographies and time zones.