Flexera saves customers billions of dollars in wasted technology spend. A pioneer in Hybrid ITAM and FinOps, Flexera provides award-winning, data-oriented SaaS solutions for technology value optimization (TVO), enabling IT, finance, procurement and cloud teams to gain deep insights into cost optimization, compliance and risks for each business service. Flexera One solutions are built on a set of definitive customer, supplier and industry data, powered by our Technology Intelligence Platform, that enables organizations to visualize their Enterprise Technology Blueprint™ in hybrid environments—from on-premises to SaaS to containers to cloud.
We’re transforming the software industry. We’re Flexera. With more than 50,000 customers across the world, we’re achieving that goal. But we know we can’t do any of that without our team. Ready to help us re-imagine the industry during a time of substantial growth and ambitious plans? Come and see why we’re consistently recognized by Gartner, Forrester and IDC as a category leader in the marketplace. Learn more at flexera.com
We’re transforming the software industry. We’re Flexera. With more than 50,000 customers across the world, we’re achieving that goal. But we know we can’t do any of that without our team. Ready to help us re-imagine the industry during a time of substantial growth and ambitious plans? Come and see why we’re consistently recognized by Gartner, Forrester and IDC as a category leader in the marketplace. Learn more at flexera.com
Flexera is transforming the way enterprises deliver IT, and we’re looking for smart and collaborative teammates to deliver on that promise by anticipating the needs of our customers and helping them solve real problems.
Position Overview:
We are seeking a highly skilled and experienced Staff Program Manager to ensure every strategic priority becomes measurable business impact by bridging vision and execution, removing roadblocks, and enabling investments that scale, delight customers, and drive profitable growth.
This role operates at both the strategic and execution levels, leading complex, cross-functional initiatives that span multiple product areas, teams, and business functions. As a Staff Program Manager, you will serve as a trusted partner to Product, Engineering, Design, and business leaders, helping shape priorities, align investments, and drive the successful delivery of initiatives that are critical to Flexera's long-term growth.
The ideal candidate combines exceptional program leadership with strong business acumen, a systems-thinking mindset, and the ability to influence outcomes across the organization without direct authority. They have a proven track record of driving large-scale initiatives from concept through execution while improving organizational effectiveness along the way.
What You'll Do:
Program Leadership
- Lead large-scale, highly complex programs that span 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 that align with company objectives.
- Establish governance frameworks, execution rhythms, and decision-making processes that drive consistent delivery across programs.
- Drive alignment across competing priorities while balancing short-term execution needs with long-term strategic goals.
Strategic Planning & Portfolio Alignment
- Partner with senior leadership to translate business strategy into actionable programs and measurable outcomes.
- Influence planning and prioritization decisions across multiple teams and product areas.
- Identify dependencies, risks, investment trade-offs, and execution constraints across the portfolio.
- Evaluate opportunities to improve organizational focus, execution efficiency, and business impact.
- Contribute to quarterly and annual planning processes through data-driven recommendations and execution insights.
Cross-Functional Leadership
- Collaborate closely with Product Management, Engineering, Design, Marketing, Sales, Customer Success, Finance, Operations, and other key stakeholders.
- Drive alignment across organizations with differing priorities and objectives.
- Serve as a central coordination point for strategic initiatives, ensuring seamless collaboration and accountability.
- Build strong relationships across teams and functions to accelerate decision-making and remove barriers to success.
Organizational Influence
- Act as a trusted advisor to leaders across the organization on program strategy, execution, and operational effectiveness.
- Influence outcomes through collaboration, data, and stakeholder engagement rather than direct authority.
- Facilitate executive discussions, helping leaders evaluate risks, trade-offs, and strategic options.
- Identify opportunities to strengthen cross-functional collaboration and improve organizational effectiveness.
Risk & Dependency Management
- Proactively identify, assess, and mitigate program risks, dependencies, and execution challenges.
- Develop mitigation strategies and contingency plans to address evolving priorities and business needs.
- Anticipate organizational, technical, and operational risks before they impact delivery.
- Drive resolution of complex issues requiring coordination across multiple teams and stakeholders.
Communication & Executive Reporting
- Provide clear and actionable updates to executives and senior stakeholders on program status, milestones, risks, and outcomes.
- Lead executive-level program reviews and drive alignment on critical decisions.
- Create transparency into program health, delivery forecasts, and strategic objectives.
- Ensure stakeholders have the information needed to make timely and informed decisions.
Process Excellence & Program Management Practices
- Define, implement, and continuously 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 a culture of accountability, collaboration, continuous improvement, and execution excellence.
Mentorship & Leadership
- Mentor and coach program managers across the organization, helping elevate program management capabilities and practices.
- Share knowledge, frameworks, and lessons learned to improve consistency and effectiveness across teams.
- Help shape the evolution of the Program Management function as the organization grows and scales.
Ideal Candidates Bring:
Experience
- 10+ years of program management experience, with a significant track record of leading complex, cross-functional initiatives in software or technology-focused organizations.
- Experience operating at a strategic level and partnering with senior leaders on business-critical initiatives.
- Proven success managing programs that span multiple teams, products, and organizational functions.
- Experience driving organizational change, operational improvements, and business transformation initiatives.
Preferred
- Strong understanding of the AI landscape, including how organizations integrate, adopt, govern, and derive business value from AI capabilities.
- Experience leading initiatives involving AI, GenAI, data platforms, developer productivity, or enterprise software products.
Skills
- Exceptional ability to navigate complexity, ambiguity, and competing priorities.
- Strong business and strategic thinking skills, with the ability to connect execution to measurable business outcomes.
- Proven ability to influence senior stakeholders and drive alignment across organizations.
- Expertise in 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.
Technical Knowledge
- 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 the following is a plus: Web Applications, Go, Ruby, JavaScript, React, microservice architectures, AWS, and Microsoft Azure.
Education
- Bachelor's degree in Business, Computer Science, Engineering, or a related field.
Tools
- Proficiency in program management tools such as JIRA, Confluence, and related planning and reporting platforms.
- Advanced proficiency with productivity tools such as Microsoft Office.
- Experience leveraging GenAI tools such as Microsoft Copilot, Claude, ChatGPT, or similar technologies to improve planning, execution, and operational effectiveness.
For Ontario residents - the base salary range for this position is estimated to be between $150,000 - $170,000 annually. Your salary will be determined by various factors, including relevant experience, skill set, qualifications, and other business needs.
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Flexera is proud to be an equal opportunity employer. Qualified applicants will be considered for open roles regardless of age, ancestry, color, family or medical care leave, gender identity or expression, genetic information, marital status, medical condition, national origin, physical or mental disability, political affiliation, protected veteran status, race, religion, sex (including pregnancy), sexual orientation, or any other characteristic protected by local/national laws, policies and/or regulations.
Flexera understands the value that results from employing a diverse, equitable, and inclusive workforce. We recognize that equity necessitates acknowledging past exclusion and that inclusion requires intentional effort. Our DEI (Diversity, Equity, and Inclusion) council is the driving force behind our commitment to championing policies and practices that foster a welcoming environment for all.
We encourage candidates requiring accommodations to please let us know by emailing [email protected].
Skills Required
- 10+ years of program management experience
- At least 3 years managing cross-functional initiatives in a software or technology-focused organization
- Bachelor's degree in business, computer science, engineering, or a related field
- Ability to manage complexity and ambiguity with strong problem-solving skills
- Experience building and managing program roadmaps and timelines
- Excellent communication and interpersonal skills with the ability to drive alignment across teams
- Familiarity with software development lifecycle, Agile methodologies, and modern product development practices
- Technical literacy across AI/GenAI systems, data, and platform architecture
- Understanding of the AI landscape and organizational AI adoption and value creation
- Experience with web applications, Go, Ruby, JavaScript, React, microservice architectures, AWS, or Microsoft Azure
- Proficiency with JIRA, Confluence, Microsoft Office, and GenAI tools such as Copilot or Claude
Flexera Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Flexera and has not been reviewed or approved by Flexera.
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Leave & Time Off Breadth — Time off policies are described as generous, with “unlimited” U.S. PTO, paid holidays, and flexibility that supports work–life balance. Usage experiences can vary by team, but the policy is consistently highlighted as a strength.
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Healthcare Strength — Health coverage is characterized as comprehensive, including medical, dental, vision, mental-health/EAP, and HSA/FSA options. This broad core lineup is consistently presented as a solid part of the package.
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Retirement Support — Retirement offerings include a 401(k) and an employee stock purchase plan, complemented by life and disability insurance. Charitable gift matching and other financial protections round out the support.
Flexera Insights
What We Do
Flexera delivers SaaS-based IT management solutions that enable enterprises to accelerate digital transformation and multiply the value of their technology investments. We help organizations inform their IT with definitive visibility into complex hybrid IT ecosystems, providing unparalleled IT insights that allow them to seize technology opportunities. And we help them transform their IT with tools that deliver actionable intelligence across an ever-increasing range of dimensions to effectively manage, govern and optimize their hybrid IT estate. More than 50,000 customers subscribe to our technology value optimization solutions, delivered by 1,300+ passionate team members worldwide. To learn more, visit flexera.com
Why Work With Us
People work here for, well, the people. People stay for the camaraderie with smart, passionate teams who actually like working together and managers who support them. We also offer competitive benefits, hybrid working and unlimited time off. Our inclusivity scores are in the top benchmark and we are consistently rated a “great place to work.”
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