Director of Contracts

2 Circle, Inc.

We are a small-veteran owned consulting firm providing specialized customer focused system engineering, requirements definition, operational analysis, and program management support to Department of Defense requirements staffs, acquisition communities, S&T organizations, and warfighters to solve mission-critical problems. Our firm leverages a strong tradition of exceptional service to our customers and the warfighter. Our reputation and experience are critical to our success and is therefore, the center of our focus. We maintain a competitive advantage by hiring the most qualified and relevant individuals, leveraging the ability to operate in multi-level security environments, providing unmitigated exceptional quality of product, and keeping our cost structure below competing consulting entities. 2 Circle Inc. seeks both people and partner companies with a commitment to excellence that will enable a best of breed product for the US and coalition warfighters.

Job Summary & Essential Job Functions

The Director of Contracts is a senior leadership role responsible for the strategic oversight, administration, and execution of all company contracts across government and commercial programs. This position partners closely with executive leadership, project management, business development, and finance to ensure contracts are structured, negotiated, and managed in alignment with organizational goals, regulatory requirements, and industry best practices. Lead the full contract lifecycle from proposal support through negotiation, award, administration, and closeout while establishing policies, processes, and controls that ensure compliance with applicable regulations, including federal acquisition frameworks. This role requires a high level of business acumen, leadership capability, and the ability to manage complex, high-value contractual relationships in a fast-paced environment.

Essential Job Functions

• Oversee all phases of contract management, including proposal review and compliance, contract negotiation and award, funding modifications and change management, and contract closeout.


• Provide hands-on leadership in complex negotiations and contractual decision making.


• Ensure proper contract setup, execution, and tracking within contract management systems.


• Direct oversight of complex federal contract portfolio, including IDIQ contracts and associated task orders, stand-alone prime contracts and SBIR awards, Technical Direction Letter (TDL) driven work structures.


• Lead subcontract strategy and administration as a prime contractor and a subcontractor to large defense primes.


• Oversee high-volume subcontract environments, including invoice review, funding tracking, and compliance.


• Ensure full compliance with FAR/DFARS and other federal contracting regulations, including subcontractor flow-downs.


• Maintain audit-ready contract files and support internal/external audits.


• Identify, assess, and mitigate contractual risks across all programs.


• Oversee contract-related aspects of classified programs, including alignment with security requirements.


• Partner with Project Managers to ensure alignment between contract requirements and program execution.


• Provide guidance on contract interpretation, deliverables, and funding limitations.


• Support proposal development, contributing to successful contract awards.


• Oversee contract startup, project configuration, and closeout processes.


• Support the review and/or creation of non-disclosure and teaming agreements.


• Provide creative leadership from knowledge of industry best practices and provides reporting to management on contract issues.

Required Qualifications

• Minimum 20+ years of progressive experience in federal government contracting, including significant experience supporting DoD and U.S. Navy programs.


• Minimum 10+ years in a leadership role within contracts management, including direct supervision of contracts personnel.


• Demonstrated experience managing large, complex contract portfolios, including IDIQs, task orders, and prime contracts.


• Extensive experience administering and negotiating all contract types.


• Proven expertise in subcontract management, including high-volume subcontract administration and invoice oversight.


• Experience supporting joint venture contracting environments under federal IDIQ structures.


• Deep knowledge of FAR, DFARS, and federal contract compliance requirements.


• Experience managing Technical Direction Letters (TDLs) or similar tasking mechanisms.


• Active Top Secret Clearance.

Preferred Qualification

• Experience serving as the primary contracts advisor to executive leadership.


• Experience supporting proposal efforts resulting in significant contract awards.


• Experience with classified contracting and security environments.


• Professional affiliation with organizations such as the National Contract Management Association (NCMA).


• Experience with Unanet or similar accounting/project management systems.


• Industry certifications (e.g., CPCM, CFCM) are a plus.

Desired Skills

• Experience with various types of Government and Commercial contracts.


• Excellent communication and writing skills.


• Proficient with Microsoft Office (Outlook, Word, PowerPoint, and Excel).


• Experience with classified contracting.

2 Circle, Inc is an Equal Opportunity/Affirmative Action employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex including sexual orientation and gender identity, national origin, disability, protected Veteran Status, or any other characteristic protected by applicable federal, state, or local law.

If you are a qualified individual with a disability or a disabled veteran, you have the right to request an accommodation if you are unable or limited in your ability to use or access our career center as a result of your disability. To request an accommodation, contact the 2 Circle, Inc. hiring manager.