Director of Program Management

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 are seeking a dynamic and experienced Head of Program Management to lead and scale our growing team of Program Managers. This role is instrumental in driving cross-functional alignment, ensuring delivery excellence, and enabling organizational growth through effective program execution. Reporting to the Head of Product and Engineering Operations, you will work closely with Product, Engineering, Go-to-Market, and Executive teams to orchestrate high-impact programs that advance our strategic objectives.

In addition to leadership responsibilities, this role includes direct program management ownership of at least one key product initiative, demonstrating hands-on expertise and setting a standard of excellence for the team.

Key Responsibilities:

• Lead, mentor, and scale a high-performing team of Program Managers, fostering career growth, executional excellence, and a focus on outcomes.

• Define and drive best-in-class program management practices, tools, and frameworks that support repeatable, predictable, and scalable delivery.

• Own the end-to-end program lifecycle, from strategic planning through execution, risk management, delivery, and post-mortem analysis.

• Personally lead and manage at least one high-priority cross-organizational program, providing direct value and setting an example of best practices in action.

• Partner with Product, Engineering, Marketing, Customer Success, and GTM leaders to ensure alignment on roadmaps, priorities, and dependencies.

• Provide executive-level reporting, insights, and recommendations to track progress against strategic goals and OKRs.

• Champion operational excellence and continuous improvement initiatives across the organization.

• Act as a strategic advisor and thought partner to the Head of Product and Engineering Operations.

Qualifications & Skills

• 10+ years of experience in program management, with at least 3 years leading and scaling teams in a software or SaaS environment.

• Demonstrated ability to manage complex programs hands-on, including recent experience driving a critical product or platform initiative from planning through delivery.

• Exceptional leadership and interpersonal skills with the ability to influence at all levels.

• Excellent communication and interpersonal skills, with the ability to build and maintain effective relationships with internal and external stakeholders.  

• Strong business acumen with a track record of aligning program execution to strategic priorities.

• Deep understanding of product development lifecycles (Agile/Lean/Scaled Agile environments).

• Experience implementing tools and processes that enable visibility, efficiency, and accountability.

• Bachelor’s degree in a related field (MBA or technical degree a plus).

Preferred Qualifications

• PMP, PgMP, or SAFe certification.

• Experience with portfolio management and financial tracking.

• Background in change management or organizational transformation.

You’ll play a pivotal role in shaping how we scale and deliver as a company. As we continue to grow, your leadership and direct contributions will help ensure we stay focused, agile, and aligned around what matters most—delivering value to our customers with precision and speed.