Senior Technical Advisor (Former CIO / CTO)

Title:

Senior Technical 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 / 10-15hrs a week (flexible based on need)

Reports to:

DHMS Program Leadership

POSITION SUMMARY

We are seeking a senior Technical Advisor (former CIO, CTO, or equivalent executive) to support Workforce 3.0 (WF3) initiatives under PEO DHMS. This is a part-time role focused on providing high-level technical guidance across complex, multi-vendor, enterprise environments. This role operates as a trusted advisor to the Technical Director and program leadership, helping guide enterprise architecture, modernization strategy, and system integration across key DHMS programs (e.g., JOMIS, MHS GENESIS, EIDS, FEHRM, Cyber).

The ideal candidate brings strong commercial experience, executive-level technical leadership, and the ability to engage directly with clients and senior stakeholders while providing practical, experience-based guidance. This is not a delivery role. This is a high-impact advisory role focused on improving decision-making, reducing risk, and strengthening technical direction across the program.

This role is intended for individuals who have operated at the enterprise executive level (CIO, CTO, or equivalent) and have led large-scale technology organizations and decision-making. Engagement will be on-demand, aligned to program needs, including scheduled sessions and ad hoc advisory support.

JOB RESPONSIBILITIES

Executive Technical Advisory

Act as a senior technical advisor across WF3 programs, guiding enterprise architecture, system integration, and overall platform strategy

Support the Technical Director with strategic technical direction and decision support across programs

Modernization and System Strategy

Provide advisory support on DevSecOps, cloud alignment, legacy system decommissioning, and cross-system interoperability

Guide modernization efforts across complex, multi-system environments with competing priorities

Vendor and Solution Oversight

Review and challenge vendor architectures and delivery approaches, identifying risks, gaps, and inefficiencies

Recommend practical, scalable solutions based on real-world executive experience

Client and Stakeholder Engagement

Lead and participate in executive-level discussions with government and commercial stakeholders, providing clear and defensible technical positions

Support executive discussions, technical reviews, and strategic alignment across multiple clients

Decision Support and Risk Management

Support leadership in key technical decisions, including tradeoffs, roadmap alignment, and prioritization

Identify risks early and provide actionable recommendations to mitigate technical and program risk

BASIC QUALIFICATIONS

Former CIO, CTO, or equivalent senior technology executive experience

15+ years leading enterprise-scale technology environments

Strong background in:

Enterprise architecture

System integration

Large-scale modernization initiatives

Experience supporting:

Multi-vendor environments

Complex, cross-functional programs

Ability to operate at both:

Executive advisory level

Deep technical strategy level

Strong ability to interface directly with clients and senior stakeholders

Strong commercial/private sector experience (preferred over DoD-only background)

Familiarity with:

Healthcare IT systems

Large enterprise platforms

Government or regulated environments (nice to have, not required)

Experience in:

Advisory or fractional executive roles

Consulting environments (Big 4, strategy firms, etc.)

Familiarity with DHMS ecosystem (e.g., JOMIS, DHMSM, MHS GENESIS, EIDS, FEHRM) is a plus

KEY COMPETENCIES

Executive-level technical judgment and decision-making

Ability to quickly assess complex systems and identify risks

Strong client-facing presence and credibility

Ability to provide independent technical judgment, including challenging leadership, vendors, and existing approaches when needed

Experience operating in ambiguous, evolving environments