Director of Contracts and Acquisition

Position Overview

Trillion Technology Solutions is seeking a highly experienced acquisition and contracts leader to serve as Director of Contracts & Acquisition Strategy. This role will leverage deep federal acquisition experience to strengthen Trillion's contract execution, proposal quality, and compliance posture across civilian and defense agencies. The Director will play a critical role in ensuring Trillion's contracts, proposals, and delivery practices align with federal acquisition regulations, while also expanding the company's ability to successfully compete for and execute complex government programs.

This position serves as a strategic bridge between government expectations and industry execution, helping position Trillion for sustained growth and operational excellence.

• Lead oversight and continuous improvement of Trillion's contract portfolio across federal agencies (FEMA, DHS, DoD, etc.)
• Provide expert guidance on FAR/DFARS compliance, contract structures, and acquisition strategies
• Ensure all contract documentation complies with federal requirements in the FAR and DFAR, including subcontracting requirements (ex: proof of insurance) and flow downs
• Establish best practices for contract management, administration, and lifecycle governance
• Support development and review of key contract artifacts (PWS, SOWs, IGCEs, J&As, acquisition strategies)
• Advise leadership on contract vehicles, pricing structures, and risk mitigation

• Improve proposal quality, compliance, and competitiveness
• Review RFP/RFQ responses for compliance and alignment with evaluation criteria
• Support capture teams in shaping acquisition strategies
• Provide insights into government source selection processes
• Mentor proposal teams on federal expectations

• Serve as internal authority on federal acquisition compliance
• Conduct contract and program reviews for regulatory compliance
• Identify and mitigate contract performance and compliance risks
• Support audit readiness, protests, and disputes

• Represent Trillion with government stakeholders
• Translate government priorities into business strategy
• Support executive engagement with federal customers
• Advise on acquisition processes and decision-making

• Improve internal contract and proposal processes
• Develop standardized templates and playbooks
• Enhance coordination across BD, capture, and delivery teams

• Support expansion into new federal opportunities
• Contribute to bid/no-bid decisions
• Align pursuit strategy with acquisition pathways and funding

• 10+ years of federal acquisition/program management experience
• Deep knowledge of FAR/DFARS and federal contracting
• Experience developing acquisition artifacts (PWS, RFPs, etc.)
• Strong executive communication and stakeholder engagement skills
• Active security clearance preferred

Trillion is an equal opportunity employer. Applicants are considered for positions without regard to race, religion, gender, native origin, age, disability, or any other category protected by applicable federal, state, or local law.