Job Description
Executive Technology Advisor (Former
CIO / CTO
) Workforce 3 Rosslyn, VA Job Details Part-time | Full-time $235 an hour 1 day ago Qualifications Stakeholder engagement Enterprise architecture Digital transformation Decision making Senior leadership Full Job Description Title:
Executive Technology Advisor (Former CIO / CTO
) Function :
Defense Healthcare Management Systems (DHMS) / Enterprise Technical Advisory Location:
Remote - ability to travel to Washington, D.C. and Rosslyn, VA as required Work Structure:
Part Time / 10-15 Hours Per Week (Flexible Based on Need) Reports to: DHMS Program Leadership POSITION SUMMARY
We are seeking an Executive Technology Advisor (former CIO, CTO, Chief Digital Officer, or equivalent enterprise executive) to support Workforce 3.0 (WF3) initiatives under PEO DHMS.
This is a part-time executive advisory role focused on providing high-level technical guidance across complex, multi-vendor, enterprise environments supporting key DHMS programs such as JOMIS, MHS
GENESIS, EIDS, FEHRM, and Cyber. This role is intended for highly seasoned enterprise technology executives who have led large-scale commercial or regulated technology organizations and modernization efforts. The ideal candidate brings executive-level technical leadership, strong commercial/private-sector experience, and the ability to engage directly with senior stakeholders while providing practical, experience-based guidance across enterprise modernization initiatives. Strong preference will be given to candidates with: Former CIO, CTO, Chief Digital Officer, or equivalent executive leadership experience Big 4 consulting, enterprise advisory, or executive transformation consulting backgrounds Enterprise modernization and technology governance leadership Large-scale system integration and enterprise architecture experience Experience operating in highly complex, multi-vendor environments Strong executive presence and stakeholder engagement capability Healthcare IT, enterprise platforms, or regulated-environment experience This is not a hands-on engineering, delivery management, or operational support role. This is a high-impact executive advisory role focused on improving enterprise decision-making, reducing technical and organizational risk, strengthening modernization strategy, and advising leadership across highly complex environments. Ideal candidates are often former enterprise executives, fractional technology leaders, transformation advisors, or consulting executives seeking high-impact advisory engagement rather than full-time operational leadership roles. JOB RESPONSIBILITIES
Executive Technical Advisory Act as a senior executive technology advisor across WF3 programs supporting enterprise architecture, modernization strategy, system integration, and organizational technology direction Support program leadership with executive-level technical guidance, strategic direction, and modernization decision support Provide independent technical judgment across enterprise modernization initiatives Modernization and Enterprise Strategy Advise on DevSecOps, cloud alignment, enterprise modernization, interoperability strategy, and legacy system decommissioning Guide modernization efforts across complex, multi-system environments with competing priorities Support enterprise roadmap alignment, modernization sequencing, and organizational technology governance Vendor, Architecture, and Solution Oversight Review and challenge vendor architectures, modernization approaches, and delivery strategies Identify technical, operational, and organizational risks across enterprise initiatives Recommend scalable, practical solutions based on real-world executive leadership experience Client and Stakeholder Engagement Participate in executive-level discussions with government and commercial stakeholders Support executive briefings, technical reviews, and strategic alignment discussions Interface directly with senior leadership, enterprise stakeholders, and vendor leadership teams Decision Support and Risk Management Support leadership in key enterprise technical decisions, tradeoff analysis, and modernization prioritization Identify risks early and provide actionable executive-level recommendations Provide independent technical judgment, including challenging assumptions and existing approaches when appropriate BASIC QUALIFICATIONS
Required Experience Former CIO, CTO, Chief Digital Officer, VP of Enterprise Technology, or equivalent executive-level leadership experience 15+ years leading enterprise-scale technology organizations and modernization initiatives Executive ownership of enterprise technology strategy, modernization governance, and enterprise transformation initiatives Strong commercial/private-sector experience preferred over exclusively government-focused backgrounds Strong ability to interface directly with executives, clients, and senior stakeholders Core Technical and Strategic Background Enterprise architecture System integration Enterprise modernization strategy Organizational technology governance Multi-vendor enterprise environments Large-scale cross-functional programs Executive technology decision-making Preferred Backgrounds Big 4 consulting Enterprise transformation consulting Fractional executive advisory Technology governance advisory Healthcare IT systems Large enterprise platforms Regulated enterprise environments DHMS ecosystem familiarity (JOMIS, MHS GENESIS, EIDS, FEHRM, Cyber) Additional Guidance Candidates whose backgrounds are primarily limited to project management, operational support, engineering delivery, or solution architecture without prior enterprise executive leadership experience are unlikely to be competitive for this role KEY COMPETENCIES
Executive-level technical judgment and enterprise decision-making Strong executive presence and client-facing credibility Ability to quickly assess complex systems, organizations, and modernization risks Strong organizational technology governance mindset Independent technical judgment and willingness to challenge assumptions when appropriate Experience operating effectively in ambiguous, evolving, and highly complex environments Strong enterprise systems thinking and modernization strategy capability
