Senior Director GWAC

Senior Director, GWAC Strategy & Execution (Enterprise)

Position Summary

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

Key Responsibilities

Enterprise GWAC Strategy & Market Leadership

• 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)

Pipeline Development & Predictive Analysis

• 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

Capture & Teaming Enablement

• 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

Governance, Discipline & Enterprise Efficiency

• 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

Leadership & Collaboration

• 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

Required Qualifications

• Bachelor's degree in Business, Engineering, Government Affairs, or a related field (required)
• MBA or Master's degree (strongly preferred)
• 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
• Experience within a Tribal, ANC, or similarly complex enterprise structure (highly desirable)

Why This Role Matters

This position is not administrative-it is strategic infrastructure. The Senior Director ensures Cherokee Federal:

• Enters vehicle cycles prepared-not constrained
• Competes where it is advantaged-not hopeful
• Converts relationships into outcomes-compliantly and consistently
• Replaces fragmentation with clarity, discipline, and foresight

This role institutionalizes proven market best practices and positions Cherokee Federal for sustained task-order success across GWACs and large IDIQs over the next decade.