Social Security Administration Enterprise Systems Executive and Senior Technology Advisor

Title: Social Security Administration Enterprise Systems Executive and Senior Technology Advisor Function: Enterprise Technology Strategy, Program Management, and Federal Information Technology Advisory Location: Remote Reports to: Executive Leadership POSITION SUMMARY: We are seeking a former senior Social Security Administration (SSA) technology leader to serve as a Senior Enterprise Technology Program Manager supporting enterprise technology operations, technical delivery, modernization, governance, and contractor-supported information technology services. The successful candidate must have held a substantive leadership role within SSA’s technology organization, with broad responsibility for major technical programs, portfolios, organizations, or enterprise services. This role requires an enterprise-level leader who can provide informed strategic advice while also taking direct responsibility for planning, coordination, execution, analysis, and deliverable development. The ideal candidate will not function solely as an advisor. This individual must be able to organize complex work, develop actionable plans, coordinate technical and operational stakeholders, assess risks, prepare executive-level materials, track progress, resolve issues, and help move initiatives from strategy through execution. The ideal candidate will have overseen multiple technical domains, including software and web development, database and data administration, software engineering and systems integration, infrastructure, systems administration, and cybersecurity. The Senior Program Manager will provide institutional knowledge, strategic guidance, hands-on program management, independent review, and practical recommendations to executive, technical, operational, and program leadership. This role will help ensure that technical, staffing, governance, transition, and delivery approaches are credible, practical, executable, and aligned with the operating environment and organizational expectations. JOB RESPONSIBILITIES: Lead and coordinate complex enterprise technology initiatives from planning through execution, including the development of work plans, schedules, priorities, deliverables, decision points, and performance measures. Provide executive-level guidance while also directly managing assigned activities, developing work products, tracking actions, and driving issues through resolution. Advise leadership on technology organizations, governance structures, decision-making processes, stakeholder roles, and contractor relationships. Translate strategic objectives and leadership direction into practical plans, clearly defined activities, accountable owners, timelines, and measurable outcomes. Coordinate with executive, program, technical, operational, acquisition, security, and contractor stakeholders to maintain alignment and support timely decision-making. Review technical, staffing, governance, transition, and operating approaches for alignment with established practices, systems, security requirements, and organizational expectations. Independently evaluate proposed technical architectures, delivery approaches, dependencies, risks, and implementation feasibility across software and web development, data and database administration, systems integration, cloud, infrastructure, systems administration, and cybersecurity. Identify, document, and manage technical, operational, organizational, integration, staffing, schedule, and transition risks that could affect delivery. Develop and maintain program-management materials, including implementation plans, schedules, action trackers, risk and issue logs, decision papers, status reports, operating procedures, and performance dashboards. Review proposed program leadership, technical leadership, team structures, escalation paths, reporting relationships, and governance processes. Lead or support large-scale technical transitions, incumbent workforce continuity, knowledge transfer, credentialing, system access, onboarding, and operational-readiness activities. Provide guidance regarding multi-vendor delivery, contractor performance, key personnel, staffing models, dependencies, and Government oversight. Develop and review executive briefings, technical narratives, management approaches, transition strategies, staffing plans, operating procedures, and performance frameworks. Facilitate leadership discussions, working sessions, solution reviews, independent assessments, and structured review sessions. Provide candid, practical recommendations based on firsthand experience and follow through on resulting decisions, actions, and deliverables. BASIC JOB REQUIREMENTS: Must be a former Social Security Administration employee who served in a senior technology leadership, executive, director, deputy director, senior program management, or comparable decision-making role. Must have held broad responsibility for a technology organization, enterprise program, portfolio, major initiative, or contractor-supported technical operation. Must have demonstrated experience managing complex technology programs or initiatives, including planning, execution, stakeholder coordination, risk management, performance tracking, and executive reporting. Must have led or overseen multiple technical areas, including software and web development, database and data administration, software engineering and systems integration, infrastructure, systems administration, or cybersecurity. Must have experience overseeing large-scale technology services, technical programs, contractors, or multi-vendor delivery environments. Must possess strong knowledge of federal technology governance, organizational structures, technical decision-making, stakeholder responsibilities, and contractor interaction. Must have experience evaluating technical delivery, program performance, quality, schedule, risk, staffing, resources, key personnel, or contractor performance. Must be able to develop high-quality program plans, executive briefings, decision materials, status reports, risk assessments, operating procedures, and other management deliverables. Must be able to operate independently, manage competing priorities, organize ambiguous requirements, and move complex activities forward with limited direction. Must be able to assess complex technical and management approaches from an enterprise and executive perspective and translate that assessment into actionable recommendations and executable plans. Experience serving as or working closely with an executive, Contracting Officer’s Technical Representative, Government program manager, technical director, program director, system owner, or senior information technology official is preferred. Experience with technology modernization, cloud, cybersecurity, data, infrastructure, digital services, enterprise architecture, systems integration, incumbent transition, credentialing, or access continuity is preferred. Experience advising senior leadership while also directly managing major technology programs, contractor-supported services, organizational change, or enterprise transformation is preferred.