Senior Director GWAC

Cherokee Federal•McLean, VA

About The Position

The Senior Director, GWAC Strategy & Execution is an enterprise leadership role responsible for owning, shaping, and executing Cherokee Federal’s strategy for Government-Wide Acquisition Contracts (GWACs) and other large IDIQ contract vehicles across all capability Business Units. This leader is strategic first, operationally disciplined, and tactically enabling—anticipating market movement, shaping acquisition pathways, and positioning Cherokee Federal for sustained task-order success over a rolling 2–3 year horizon. Serving as the single authoritative voice for enterprise GWAC/IDIQ strategy with GSA AAS, FEDSIM, and major ordering activities, the Senior Director synchronizes enterprise priorities with Business Unit execution to ensure Cherokee competes from a position of advantage rather than reaction. The role informs vehicle selection, qualification strategy, teaming, certification planning, and pursuit discipline—replacing fragmented, reactive engagement with deliberate foresight and repeatable execution. This position is mission-critical to enterprise performance across ATS, Health, Logistics & Sustainment Operations (LSO), PETS, and emerging capability areas, and serves as the central strategic and governance hub for Cherokee’s GWAC ecosystem. Strategic Scope of Responsibility The Senior Director is accountable for three integrated layers of enterprise performance: 1) Strategic (Enterprise-Level Ownership) Own and maintain a rolling 2–3 year GWAC/IDIQ roadmap, including (as applicable): GSA OASIS / OASIS+ (all relevant domains) GSA ASTRO CIO-SP4 Alliant / Alliant 3 Army MAPS Other emerging civilian and defense-wide contract vehicles Anticipate qualification requirements, certifications, teaming needs, and capability gaps well in advance of solicitation release Shape enterprise posture and investment decisions related to contract vehicles—not just individual pursuits Serve as the senior strategic interface to GSA AAS leadership and broader GWAC ecosystem stakeholders 2) Operational (GWAC PMO Leadership) Direct and govern a centralized GWAC PMO responsible for: Opportunity intake, screening, and prioritization Predictive pipeline analysis and qualification discipline Alignment of vehicle strategy to corporate growth objectives Establish and enforce standardized GWAC processes, decision gates, and an execution cadence that drives accountability Ensure clean, compliant, and efficient handoff of pre-qualified opportunities to Business Units 3) Tactical Enablement (Business Unit Execution) Enable BU BD, Capture, and Proposal teams through: Early acquisition intelligence Clear vehicle positioning guidance Pre-qualified, evaluation-ready opportunities Ensure BUs engage only where Cherokee is strategically positioned and operationally advantaged Reduce low-probability, reactive pursuits through enterprise screening, qualification, and governance

Requirements

Bachelor’s degree in Business, Engineering, Government Affairs, or a related field (required)
15+ years of progressive experience in federal contracting, with deep specialization in: GWACs and large IDIQs Strategic capture and proposal operations GSA AAS and FEDSIM environments
Demonstrated record of contract wins and/or portfolio leadership across major vehicles (e.g., OASIS+/OASIS, ASTRO, HCaTS, EIS, FAA IDIQs, and similar)
Proven experience serving as: IDIQ/GWAC Program Manager or enterprise vehicle leader for significant portfolios, and/or Strategic capture leader on large, complex pursuits
Deep knowledge of FAR-based acquisition strategies, ordering activity behaviors, and GWAC execution models
Established relationships with stakeholders across: GSA AAS leadership Program Managers and ordering activity personnel
Experience operating across both DoD and civilian agencies

Nice To Haves

MBA or Master’s degree (strongly preferred)
Experience within a Tribal, ANC, or similarly complex enterprise structure (highly desirable)

Responsibilities

Develop and execute Cherokee Federal’s enterprise GWAC/IDIQ strategy aligned to long-term growth objectives and portfolio priorities
Serve as Cherokee’s senior, trusted point of engagement with GSA AAS, PMRs, Shared Interest Groups (SIGs), and ordering activities
Shape acquisition approaches through compliant, early engagement with customers on: Scope realism Contracting pathways Evaluation constructs and scoring strategies
Maintain active leadership and visibility within the GWAC ecosystem (e.g., ASTRO and OASIS+ SIGs and industry forums)
Build and manage a forward-looking GWAC pipeline informed by: Historical award patterns Customer buying behavior Market saturation analysis Emerging scoring and evaluation trends
Use predictive analysis to guide: Vehicle investments and re-compete posture Teaming/partner strategy Capability development priorities and enterprise readiness plans
Provide senior-level capture leadership and advisory support on high-value GWAC pursuits
Conduct enterprise gap analyses across Cherokee LLCs to identify best-positioned entities for specific task orders
Identify, vet, and structure external partnerships to strengthen competitive positioning and compliance posture
Ensure capture strategies align to vehicle intent, customer acquisition strategy, and evaluation realities
Eliminate redundant GWAC efforts across operating companies through central governance and clear decision rights
Improve enterprise win-rate efficiency by reducing churn, misaligned pursuits, and late-stage surprises
Establish Cherokee Federal as a disciplined, credible, and valued partner within the GWAC community through consistent execution and relationship stewardship
Leads a centralized GWAC PMO function and influences cross-functional teams across Business Units, BD/Capture/Proposal, Solutioning, Pricing, Contracts, and Compliance
Partners closely with executive leadership to align vehicle posture with enterprise growth, investment decisions, and risk tolerance
Operates with high integrity and strict compliance with FAR/ethics rules governing customer engagement and procurement communications