Executive Strategy & Portfolio Lead – DHMS Executive Operations

Title:

Executive Strategy & Portfolio Lead – DHMS Executive Operations

Function:

Program Executive Office, Defense Healthcare Management Systems (PEO DHMS)

Location:

Onsite in Rosslyn, VA – 5 days per week

Reports to:

Deputy Program Executive Officer (Deputy PEO DHMS)

POSITION SUMMARY:

The Executive Strategy & Portfolio Lead serves as a senior leadership partner within the DHMS Executive Office, supporting executive decision-making, strategic alignment, and portfolio-level execution across a complex enterprise environment.

This role sits inside the leadership operating layer and works directly alongside senior government stakeholders to help shape how priorities are defined, how decisions are made, and how execution remains aligned with executive intent. The position operates across organizational boundaries, connecting strategy, governance, and portfolio execution to ensure leadership decisions translate into measurable outcomes.

Success in this role depends heavily on executive presence and communication style. The ideal candidate can enter senior-level conversations, rapidly absorb context, communicate with clarity and confidence, and articulate complex organizational or technical topics with ease. The ability to ramp quickly, establish credibility early, and contribute meaningfully at the leadership level will be a primary differentiator.

JOB RESPONSIBILITIES:

Governance and Organizational Effectiveness

Support efforts to refresh and improve governance processes, including how strategic decisions are made and escalated

Help leaders clarify roles, responsibilities, and decision ownership within a product or portfolio environment, from senior / executive leadership down through product / project execution

Assist with organizational design changes and help ensure new structures are adopted in day-to-day work

Executive Meetings and Leadership Support

Help redesign executive meetings so they focus on cost, schedule, performance, and results rather than status updates; ensure successful implementation of the redesigned meeting structure

Develop clear meeting agendas, pre-read materials, and decision summaries

Capture decisions, action items, owners, and deadlines to ensure follow-through

Strategic thought partnership and leadership

Lead (as directed) key strategic transformation initiatives designed to elevate the level of performance of our own team as well as the client’s

Contribute experience, expertise, and sound judgment to strategic discussions and planning sessions

Proactively share insights that contribute to improvement

Product Portfolio and Change Support

Support organization and prioritization of product and capability portfolios

Help leadership understand tradeoffs across priorities, funding, capacity, and execution risk

Translate leadership decisions into clear operational guidance that teams can execute effectively.

DHMS Executive Office Operations

Support daily operations of the DHMS Executive Office and priority initiatives

Coordinate taskers, leadership requests, and cross-team actions

Draft and coordinate executive briefings, decision memos, and leadership materials

Execution Tracking and Visibility

Track leadership commitments, dependencies, and risks

Maintain simple, clear trackers so leaders can see progress and issues

Identify gaps or delays and help drive resolution

BASIC JOB REQUIREMENTS:

Minimum of 5–7 years of experience supporting senior leaders in a Chief of Staff, PMO, or executive operations role

Experience working in a software, product, or portfolio-driven organization

Experience operating within complex enterprises or government environments supporting senior leadership

Demonstrated success in executive operations, governance leadership, strategy execution, or Chief of Staff adjacent roles

Exceptional executive communication skills with the ability to engage confidently with senior government stakeholders

Proven ability to synthesize complex information into concise, leadership-ready messaging

Ability to rapidly absorb context and operate effectively in highly seasoned leadership environments

Strong organizational judgment, professional maturity, and discretion

Ability to influence across functions without direct authority

U.S. Citizen.

Ability to work onsite in Rosslyn, VA five days per week

KEY COMPETENCIES:

Executive presence and composure in senior leadership environments

Clear, confident communication style appropriate for executive audiences

Strong organizational awareness and political intelligence

Strategic thinking paired with execution discipline

Ability to frame issues in terms of decisions, tradeoffs, and outcomes

High tolerance for ambiguity with strong follow-through

PREFERRED CERTIFICATIONS OR EXPERIENCE (Not Required):

Prosci Change Management Certification (ADKAR Model)

Project Management Professional (PMP)

Information Technology Infrastructure Library Version 4 Foundation (ITIL 4 Foundation)

Scaled Agile Framework Lean Portfolio Management Certification (SAFe LPM)

Experience implementing AI solutions / products / process improvements