We are seeking a highly skilled and experienced Staff Program Manager to ensure every strategic priority becomes measurable business impact - bridging vision and execution, removing roadblocks, and enabling investments that scale, delight customers, and deliver profitable growthThis role will require coordination of cross-functional workstreams within a defined area of the company’s product portfolioProgram Leadership:Lead the end-to-end planning, execution, and delivery for existing product releases and new product offeringsDefine the program roadmap, milestones, and success metrics in alignment with organizational goalsCross-Functional Coordination:Collaborate with teams across product management, engineering, design, marketing, sales, and customer success to ensure alignment and seamless executionServe as a key point of contact and communication hub for all program-related activitiesStrategic Alignment:Work with program leadership to ensure the program’s goals align with the company’s strategic visionIdentify dependencies and synergies across the product portfolio to maximize impactRisk Management:Proactively identify, assess, and mitigate program risks and issuesDevelop contingency plans and adapt program strategies as needed to ensure on-time and high-quality deliveryCommunication and Reporting:Provide regular updates to stakeholders, including executives, on program progress, risks, and milestonesEnsure transparency and clarity in program status and decision-making processesProcess Improvement:Leverage best practices for program management,



driving operational excellence and continuous improvementContribute to a culture of learning and collaboration with other program managers within the organizationBenefits

Student loan debt relief and tuition reimbursementCompetitive payRetirement and employee investment programHealth and wellbeingCompetitive time off, hybrid work and new-parent supportConnection through ERGs, giving and celebrationProven expertise in building and managing program roadmaps and timelinesExcellent communication and interpersonal skills, with the ability to drive alignment across teamsProficiency in program management tools such as JIRA and Confluence, productivity tools such as Microsoft Office, and GenAI tools such as Copilot or ClaudeTechnical literacy across AI/GenAI systems, data, and platform architectureThe ideal candidate will have a proven track record of managing complex, large-scale programs, collaborating with diverse stakeholders, and driving results in a rapid-paced environmentExperience with web applications, Go, Ruby, JavaScript, React, microservice architectures, AWS, or Microsoft AzureStrong understanding of the AI landscape, including how organizations integrate, adopt, and derive business value from AI capabilitiesFamiliarity with the software development lifecycle (SDLC), Agile methodologies, and modern product development practicesExceptional ability to manage complexity and ambiguity, with strong problem-solving skills10+ years of program management experience, with at least 3 years managing cross-functional initiatives in a software or technology-focused organizationBachelor’s degree in business, computer science, engineering, or a related field

📌 Staff Program Manager (Winnipeg)
🏢 Flexera
📍 Winnipeg