Leidos Chief Information Office, reporting through the Digital Modernization sector, is seeking a Senior Licensing Specialist to join the Corporate CIO Services, IT Asset Management team. In this role, you will serve as the enterprise subject matter expert for Microsoft, Adobe, and Oracle licensing, providing strategic guidance to ensure compliance, cost optimization, and alignment with business objectives. To be successful, you will bring deep expertise in enterprise software licensing, contract structures, and can influence licensing strategy across a global, complex, hybrid environment. Additionally, you will partner closely with IT, procurement, legal, finance, and business sectors to drive effective licensing solutions, ensure contractual compliance while conserving cost.

Location: This position offers full time telework from any U.S. based location.

Citizenship: US Citizenship is required.

Primary Responsibilities

• Serve as enterprise licensing SME for Microsoft, Adobe, and Oracle products, licensing structure, and agreements.

• Provide strategic oversight of licensing programs, including optimization, compliance, and cost management initiatives.

• Drive and influence licensing strategy across unique and complex business needs

• Support the business in making licensing and tooling decisions, based users’ business requirements

• Develop a relationship with vendors and third-party suppliers for licensing model knowledge transfer, and strategic licensing decisions.

• Understand and communicate the footprint and usage for Microsoft, Adobe, and Oracle in the Leidos environment

• Interpret and advise on contract types including:

  • Microsoft Enterprise Agreements (EA), MPSA, Server & Cloud Enrollment)

  • Adobe Enterprise Term License Agreements (ETLA) and VIP

  • Oracle ULA, ordering documents, and cloud subscriptions

• Analyze licensing consumption and reconcile usage against entitlements.

• Lead True-Up processes and support contract renewals and negotiations.

• Ensure compliance with licensing terms, and contractual obligations.

• Provide proactive guidance on product lifecycle changes (EOL/EOS), licensing model shifts, and policy updates.

• Develop and maintain enterprise licensing documentation and knowledge repositories.

• Partner with system lifecycle managers, procurement and legal during amendments, renewals, and vendor negotiations.

• Provide licensing recommendations during mergers, acquisitions, or subsidiary integrations.

• Oversee and manage software vendor portals as needed

Required Qualifications

• Bachelor’s degree and 6–8+ years of experience in enterprise software licensing, compliance, or licensing strategy. Master's degree and 4-6 years or equivalent relevant experience may be considered in lieu of a degree.

• Demonstrated expertise in Microsoft licensing (on-premises, subscription, M365).

• Working knowledge of Adobe and Oracle licensing models and enterprise agreements.

• Experience supporting audits and compliance reviews.

• Strong analytical skills with ability to interpret complex contractual language.

• Ability to collaborate cross-functionally with IT, procurement, legal, finance, and business stakeholders providing customer service.

• Strong written and verbal communication skills.

• Ability to work independently and influence strategic decision-making.

• US Citizenship.

Preferred Qualifications

• Experience with IT Asset Management (ITAM) principles and Software Asset Management (SAM).

• Familiarity with ServiceNow and SAMPro.

• Experience supporting contract negotiations or enterprise renewals.

• Understanding of hybrid cloud and regulated environments.

If you're looking for comfort, keep scrolling. At Leidos, we outthink, outbuild, and outpace the status quo — because the mission demands it. We're not hiring followers. We're recruiting the ones who disrupt, provoke, and refuse to fail. Step 10 is ancient history. We're already at step 30 — and moving faster than anyone else dares.

Original Posting:

Pay Range:

The Leidos pay range for this job level is a general guideline only and not a guarantee of compensation or salary. Additional factors considered in extending an offer include (but are not limited to) responsibilities of the job, education, experience, knowledge, skills, and abilities, as well as internal equity, alignment with market data, applicable bargaining agreement (if any), or other law.