Staff Program Manager

Flexera

. Lead large-scale, highly complex programs spanning multiple product, engineering, and business teams .

Posted 11/4/2026full-timeRemote • CanadaLead💰 CA$150,000 - CA$170,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates extensive program management expertise with a focus on leading complex, cross-functional initiatives and driving organizational change. Proficient in strategic planning, execution frameworks, and leveraging AI capabilities to enhance business transformation.

Highest-signal resume keywords

10+ Years Of Program Management ExperienceExpertise In Leading Complex Cross-Functional InitiativesStrong Understanding Of AI LandscapeProficiency In JIRA And ConfluenceStrong Analytical And Problem-Solving Capabilities

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Program ManagementStrategic PlanningRoadmap DevelopmentData-Driven Decision MakingAgile MethodologiesSoftware Development Lifecycles (SDLC)AI/GenAI SystemsCloud ArchitectureMicroservice ArchitecturesTechnical Literacy

Soft Skills

Outstanding Communication SkillsStakeholder ManagementNegotiation SkillsFacilitation SkillsCollaboration

Tools & Technologies

Microsoft OfficeJIRAConfluenceGenAI ToolsAWSMicrosoft Azure

Industry Keywords

Business TransformationOperational ImprovementsCross-Functional CollaborationProgram EffectivenessOrganizational Change

Tech Stack

Tools & technologies

AWSAzureCloudDistributed SystemsJavaScriptReactRubySDLCGo

About the role

Key responsibilities & impact

Lead large-scale, highly complex programs spanning multiple product, engineering, and business teams
Own end-to-end planning, execution, and delivery for strategic initiatives, product launches, platform investments, and operational transformation efforts
Define program roadmaps, milestones, success metrics, and operating models aligned with company objectives
Establish governance frameworks, execution rhythms, and decision-making processes
Drive alignment across competing priorities and balance short-term execution with long-term strategic goals
Translate business strategy into actionable programs and measurable outcomes with senior leadership
Influence planning and prioritization decisions across teams and product areas
Identify dependencies, risks, investment trade-offs, and execution constraints
Improve organizational focus, execution efficiency, and business impact
Contribute to quarterly and annual planning through data-driven recommendations and execution insights
Collaborate with Product Management, Engineering, Design, Marketing, Sales, Customer Success, Finance, Operations, and other stakeholders
Serve as a central coordination point for strategic initiatives
Build cross-functional relationships to accelerate decisions and remove barriers
Advise organizational leaders on program strategy, execution, and operational effectiveness
Facilitate executive discussions concerning risks, trade-offs, and strategic options
Identify opportunities to improve cross-functional collaboration and organizational effectiveness
Identify, assess, and mitigate program risks, dependencies, and execution challenges
Develop mitigation strategies and contingency plans
Drive resolution of complex issues requiring cross-team coordination
Provide executives and senior stakeholders with updates on status, milestones, risks, and outcomes
Lead executive-level program reviews and align stakeholders on critical decisions
Create transparency into program health, delivery forecasts, and strategic objectives
Define, implement, and improve program management frameworks, standards, and best practices
Drive operational excellence through scalable processes, tooling, and governance
Measure and improve program effectiveness using data, metrics, and feedback
Champion accountability, collaboration, continuous improvement, and execution excellence
Mentor and coach program managers across the organization
Share knowledge, frameworks, and lessons learned
Help shape the evolution of the Program Management function

Requirements

What you’ll need

10+ years of program management experience
Significant track record leading complex, cross-functional initiatives in software or technology-focused organizations
Experience operating strategically and partnering with senior leaders on business-critical initiatives
Proven success managing programs spanning multiple teams, products, and organizational functions
Experience driving organizational change, operational improvements, and business transformation initiatives
Strong understanding of the AI landscape, including organizational integration, adoption, governance, and business value of AI capabilities
Experience leading initiatives involving AI, GenAI, data platforms, developer productivity, or enterprise software products
Ability to navigate complexity, ambiguity, and competing priorities
Strong business and strategic thinking skills
Ability to influence senior stakeholders and drive organizational alignment
Expertise building and managing roadmaps, milestones, and execution frameworks for large-scale initiatives
Outstanding communication, facilitation, negotiation, and stakeholder management skills
Strong analytical and problem-solving capabilities with a data-driven decision-making approach
Strong understanding of software development lifecycles (SDLC), Agile methodologies, and modern product development practices
Technical literacy across AI/GenAI systems, data platforms, cloud architecture, and distributed systems
Ability to engage effectively with engineering and product teams on technical topics and strategic trade-offs
Experience with one or more of Web Applications, Go, Ruby, JavaScript, React, microservice architectures, AWS, and Microsoft Azure is a plus
Bachelor's degree in Business, Computer Science, Engineering, or a related field
Proficiency in JIRA, Confluence, and related planning and reporting platforms
Advanced proficiency with Microsoft Office
Experience leveraging GenAI tools such as Microsoft Copilot, Claude, ChatGPT, or similar technologies

Benefits

Comp & perks

Remote work arrangement
Equal opportunity employer
Diversity, equity, and inclusion commitment
Workplace accommodations available upon request