Strategic Deputy, Senior-Level

Overview

Strategic Deputy to CROCS Director – Hybrid | Pentagon-based (40%)Clearance: Secret Required | Top Secret PreferredLocation: Washington, DC | Hybrid (3 days/week onsite at the Pentagon)

Our client—a high-visibility defense initiative—is seeking a Strategic Deputy to support the Cyber Resiliency Office for Combat Systems (CROCS). This senior-level role partners directly with the CROCS Director to shape strategy, secure resourcing, and institutionalize change across the Air Force and broader DoD. It’s a unique opportunity for a seasoned Pentagon insider to make enterprise-level impact in cyber resilience and tech modernization.

This role demands political acumen, deep knowledge of the PPBE process, and a talent for navigating inter-agency dynamics to drive decisions at the highest levels. You’ll advocate for cyber resiliency priorities across OSD, Air Staff, and Joint Staff, helping transform technical requirements into decision-grade strategies backed by innovative funding.

Responsibilities

• Serve as Principal Deputy to the CROCS Director, driving strategic alignment between cyber resiliency goals and broader Air Force and OSD priorities.
• Lead POM Cycle Strategy & Execution, synchronizing programming guidance, budget formulation, and execution reviews across the Air Force PPBE process.
• Represent CROCS in Senior Forums, including OSD CAPE deliberations, advocating for cyber requirements and shaping enterprise-level funding and strategy decisions.
• Develop Executive-Level Briefings, transforming technical objectives into decision-quality briefs, white papers, and memos for SES and Flag Officers.
• Coordinate Multi-Agency Actions, managing staff packages and stakeholder alignment across MAJCOMs, Air Staff, and DoD organizations.
• Build High-Level Relationships, leveraging influence across the Pentagon to facilitate decision-making and secure enterprise backing.
• Innovate Funding Strategies, identifying non-traditional resourcing options and crafting agile business cases to accelerate mission delivery.
• Lead Process Improvement & Change Management, enhancing governance, auditability, and performance-based resource allocation across the cyber resiliency enterprise.

Qualifications

Required Skills:

• 8+ years in a senior advisory or deputy role supporting Air Staff, OSD, or Joint Staff operations
• Expert political navigator with track record of influencing senior decisions within OSD or the Secretariat
• Strong knowledge of PPBE; proven ability to use it as a strategic enabler, not just a compliance mechanism
• Demonstrated experience securing non-traditional DoD funding (OTAs, Readiness funds, etc.)
• Exceptional communicator—experienced with Flag/SES audiences and executive-level documentation

Preferred Skills:

• “Rainmaker” mentality: proactive in identifying new authorities, funding channels, or partnerships
• Proven leader of cross-agency working groups with complex missions
• Agile thinker who can shift strategies as policy or leadership changes
• Trusted representative for high-visibility engagements inside and outside the Pentagon

Compensation:

• Hourly rates start at $80, are based on experience, qualifications, and certifications, and are subject to change at any time.
• Benefits vary by compensation type and may include paid time off (PTO), medical, dental, and vision coverage, life insurance, long-term disability insurance, a 401(k) plan, and additional optional benefits.

4 Reasons to Join The Squires Group, Inc.: 1. Our Commitment to You - We offer competitive pay, multi-year projects, and a list of exciting clients.2. Work-Life Balance - We work hard; we work smart and have quality time for family and "life." 3. Golden Rule - We treat our consultants the way we want to be treated: with integrity, professionalism, and trust.4. We Care About You – We help you meet your career goals and continuously support your efforts in the field.

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