Program Manager – Federal IT / Digital Transformation

Position Title: Program Manager – Federal IT / Digital Transformation 
Location: Remote (U.S.) with Occasional Travel 
Client: Federal / Public Sector Programs 
Work Authorization: Candidates must be authorized to work in the United States. U.S. Citizenship may be required based on client assignment. 

📩 To apply, please submit your resume to careers@wintrio.com or complete the application form below. 

Job Summary 

WINTrio LLC is seeking an experienced Program Manager – Federal IT / Digital Transformation to lead complex technology initiatives supporting Federal agencies and mission-focused programs. 

This role combines strategic program leadership with technical oversight across cybersecurity, cloud modernization, DevSecOps, data engineering, enterprise platforms, and application modernization efforts. The successful candidate will manage multidisciplinary teams, oversee contract delivery, coordinate executive-level stakeholders, and ensure successful execution of program objectives while maintaining compliance with Federal security, governance, and performance requirements. 

The ideal candidate will possess strong leadership, communication, and organizational skills, along with demonstrated experience managing enterprise-scale Federal IT programs. This position is ideal for a technology leader who can effectively bridge mission requirements, business objectives, and modern technology solutions within Federal environments. 

Key Responsibilities 

• Lead execution of large-scale Federal IT and digital transformation programs supporting agency mission objectives. 

• Provide overall program leadership, governance, and strategic direction across cybersecurity, cloud, DevSecOps, data modernization, and application modernization initiatives. 

• Manage program scope, schedule, budget, staffing, risks, issues, and contract performance. 

• Oversee technical delivery across AWS GovCloud, Azure Government, hybrid cloud, and on-premises environments. 

• Ensure compliance with Federal security and compliance requirements, including NIST Risk Management Framework (RMF), NIST SP 800-53, FISMA, FedRAMP, and Zero Trust Architecture principles. 

• Manage Integrated Master Schedules (IMS), risk registers, issue logs, action item tracking, and Plans of Action and Milestones (POA&M). 

• Provide oversight for Authority to Operate (ATO) activities, continuous monitoring, vulnerability management, audit readiness, and compliance initiatives. 

• Drive adoption of Agile, DevSecOps, automation, and continuous improvement practices. 

• Lead cross-functional teams consisting of project managers, engineers, architects, cybersecurity specialists, developers, analysts, and subcontractors. 

• Establish and monitor Key Performance Indicators (KPIs), Service Level Agreements (SLAs), and program performance metrics. 

• Prepare and deliver executive briefings, status reports, contract deliverables, and stakeholder presentations. 

• Coordinate technical integration efforts involving APIs, microservices, enterprise applications, data platforms, and cloud services. 

• Support capture, transition, and onboarding activities for new task orders and program initiatives. 

• Build and maintain strong relationships with Government customers, partners, and stakeholders. 

• Ensure successful execution of contract deliverables while maintaining quality, schedule, and performance objectives. 

Required Qualifications 

• Bachelor’s degree in Information Technology, Computer Science, Engineering, Management Information Systems, Business Administration, or a related field. 

• Minimum ten (10) years of experience managing Federal IT programs with technical delivery responsibilities. 

• Demonstrated experience leading cybersecurity, cloud modernization, DevSecOps, data engineering, digital transformation, or application modernization initiatives. 

• Experience managing Federal contracts, task orders, or enterprise technology programs. 

• Strong understanding of Federal compliance and security frameworks, including RMF, FISMA, FedRAMP, and NIST standards. 

• Experience managing cloud-based programs utilizing AWS, Azure, or hybrid cloud environments. 

• Experience leading multi-team, multi-vendor, and geographically dispersed delivery environments. 

• Strong written and verbal communication skills. 

• Strong organizational, leadership, and stakeholder management abilities. 

• Ability to manage multiple priorities and complex program requirements simultaneously. 

Technical Areas 

Program & Delivery Management 

• Federal IT Program Management 

• Program Governance 

• Contract Performance Management 

• Risk Management 

• Agile Delivery 

• Stakeholder Engagement 

• Executive Reporting 

• Strategic Planning 

Cybersecurity & Compliance 

• NIST Risk Management Framework (RMF) 

• NIST SP 800-53 

• FISMA 

• FedRAMP 

• Zero Trust Architecture 

• ATO Support 

• Continuous Monitoring 

• Vulnerability Management 

Cloud & Modernization 

• AWS GovCloud 

• Microsoft Azure Government 

• Hybrid Cloud Architectures 

• Cloud Migration 

• Infrastructure Modernization 

• Application Modernization 

• Enterprise Integration 

DevSecOps & Automation 

• CI/CD Pipelines 

• Infrastructure as Code (IaC) 

• Automated Testing 

• DevSecOps Practices 

• Continuous Delivery 

Data & Enterprise Platforms 

• Data Modernization 

• Data Engineering 

• Analytics Platforms 

• Enterprise Applications 

• APIs and Microservices 

Tools & Platforms 

• AWS GovCloud 

• Microsoft Azure Government 

• JIRA 

• Confluence 

• ServiceNow 

• Microsoft Project 

• Splunk 

• eMASS 

• Xacta 

• Terraform 

• GitLab CI/CD 

• GitHub Actions 

• Jenkins 

Preferred Certifications 

• Project Management Professional (PMP) 

• Certified Information Systems Security Professional (CISSP) 

• Certified Information Security Manager (CISM) 

• AWS Certified Solutions Architect 

• Azure Solutions Architect Expert 

• SAFe Program Consultant (SPC) 

• SAFe Agilist 

• Certified Cloud Security Professional (CCSP) 

• ITIL Foundation or Higher 

Preferred Qualifications 

• Experience managing IDIQ, BPA, GWAC, or task order-based Federal contracts. 

• Familiarity with Zero Trust Architecture implementation initiatives. 

• Experience supporting large-scale data platforms, analytics environments, or enterprise modernization efforts. 

• Experience supporting Federal civilian, defense, or intelligence community agencies. 

• Experience leading geographically dispersed teams and subcontractor networks. 

• Experience supporting programs involving cloud migration, cybersecurity modernization, or enterprise digital transformation initiatives. 

Work Environment 

• Full-time position. 

• Remote within the United States. 

• Standard business hours Monday through Friday. 

• Occasional travel may be required in support of customer meetings, program reviews, and project activities. 

WINTrio Benefits 

• Healthcare (Medical, Dental, and Vision) 

• Flexible Spending Account (FSA) and Health Savings Account (HSA) 

• 401(k) and Retirement Savings Plan 

• Annual Bonus and Profit Sharing Opportunities 

• Paid Time Off (PTO) and Vacation 

• Employee Assistance Program (EAP) 

• Life, Personal, and Voluntary Disability Insurance 

Growth Opportunities 

There is ample opportunity to grow in multiple dimensions, including Artificial Intelligence (AI), Machine Learning (ML), cybersecurity, cloud modernization, DevSecOps, data modernization, program management, and business development. We are a completely employee-driven company, and our continued success is built on the talent, dedication, and innovation of our team members. 

Equal Opportunity Employer 

WINTrio LLC is an Equal Opportunity/Affirmative Action Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, gender identity, sexual orientation, national origin, age, disability, protected veteran status, or any other characteristic protected by applicable federal, state, or local law.