Hillary J. Freund

Overview

Hillary J. Freund is a government contracts attorney and litigator in Holland & Knight's Washington, D.C., office. Ms. Freund has extensive experience advising companies across the full life cycle of federal procurement and federal financial assistance. She represents clients ranging from emerging technology firms and small businesses to large contractors, providing practical business-oriented guidance rooted in deep regulatory knowledge.

Ms. Freund's practice spans litigation, compliance counseling, transactional support and strategic planning for companies navigating complex federal requirements. She is known for her ability to translate intricate regulatory frameworks into actionable advice, bringing clarity to high-stakes disputes and structuring compliance and competitive business arrangements.

Ms. Freund advocates for clients in high-stakes government contracts litigation involving federal procurements and frequently supports corporate transactions involving government contractors, where specialized regulatory analysis is critical to closing deals efficiently and preserving contract value. She partners with clients to build, enhance and implement government contracts and grants compliance programs tailored to each client's size and operational footprint.

In addition, Ms. Freund regularly advises recipients and subrecipients on the full spectrum of federal financial assistance and non-traditional funding mechanisms. Her practice includes not only traditional grant and cooperative agreement issues but also experience advising non-traditional defense contractors and emerging technology companies on Commercial Solution Openings (CSOs) and Other Transaction Agreements (OTAs) used by agencies to accelerate innovation outside the traditional Federal Acquisition Regulation (FAR)-based methods.

Ms. Freund also has extensive experience guiding clients through sensitive government inquiries and internal investigations and enforcement matters where early strategy and proactive engagement are critical to ensuring business continuity. She has particularly deep experience guiding companies through the complex landscape of U.S. Small Business Administration (SBA) programs.

Representative Experience

Bid Protests. Represents protesters and intervenors before the U.S. Government Accountability Office (GAO), U.S. Court of Federal Claims (COFC) and at the agency or ombudsman level, including challenges involving evaluation errors, organizational conflicts of interest, technical acceptability determinations, past performance evaluations, and cost or price realism and reasonableness.
Claims and Disputes. Prepares requests for equitable adjustments and litigates claims under the Contracts Disputes Act (CDA) before the boards of contract appeals and COFC, including disputes involving constructive changes, delays, terminations for convenience or default, cost allowability and payment controversies.
U.S. Small Business Administration (SBA) Size and Status Protests. Represents clients before the SBA and Office of Hearings and Appeals (OHA) in connection with size protests and appeals involving affiliation, ostensible subcontractor issues and joint venture eligibility.

Affiliation Counseling. Advising on SBA affiliation rules, including common ownership, identity of interest, economic dependence, ostensible subcontractor analyses and negative control while helping clients structure relationships to maintain eligibility.
Joint Ventures and Mentor-Protégé. Drafting SBA-compliant joint venture agreements, mentor-protégé agreements, including advising and ensuring compliance with performance of work and subcontracting limitations, to protect both small and large business interests.
Set-Aside Eligibility. Advising on 8(a) and others socioeconomic eligibility issues, including recertification, changes in ownership and ongoing compliance obligations.
Subcontracts and Teaming Agreements. Negotiating and drafting teaming agreements and federal subcontracts tailored to each client's business model, risk tolerance and strategic objectives, as well as ensuring compliance with flow-down requirements and domestic preference policies.

Uniform Guidance Compliance. Implementing and assessing compliance programs under 2 C.F.R. Part 200, including cost principles, procurement standards, internal controls, property management and subrecipient monitoring.
Award Administration. Counseling on prior approvals, budget realignments, reporting obligations and interactions with federal awarding agencies, including the U.S. Department of Energy (DOE), U.S. Department of Homeland Security (DHS), Federal Emergency Management Agency (FEMA), U.S. Agency for International Development (USAID) and U.S. Environmental Protection Agency (EPA).
Other Transaction Agreements (OTAs) and Prototype Projects. Advising clients on CSO submissions, as well as the structure, negotiation and administration of OTAs, including cost-sharing obligations and intellectual property (IP)/data rights considerations.
Termination, Suspension and Disallowances. Advising on remedies, disputes, negotiations and appeals involving questioned or disallowed costs, adverse audit findings and termination actions.
Subrecipient, OTAs and Consortium Structure. Drafting and negotiating subrecipient agreements, consortium arrangements and OTAs, along with balancing federal obligations with partner-specific risks and objectives.

Due Diligence. Conducting focused diligence on FAR and Defense Federal Acquisition Regulation Supplemental (DFARS) compliance, pricing systems, contract portfolios, cybersecurity obligations, domestic preference requirements, small business representations and past performance risk.
Small Business Change-of-Control Impacts. Evaluating how ownership changes affect size status, mentor-protégé relationships, joint ventures and ongoing set-aside contracts, as well as advising on recertification requirements and contract novation strategies.
Integration Planning. Advising on compliance program integration, internal controls, mandatory disclosure obligations and contract administration processes post-closing.

development of corporate policies, internal controls, training materials and compliance manuals consistent with FAR requirements
risk assessments and gap analyses related to procurement integrity, ethics, domestic preference requirements and small business certifications
creation of internal reporting processes, monitoring mechanisms and corrective action protocols

responding to Civil Investigative Demands (CID) and Office of Inspector General (OIG) inquiries and audits
conducting internal investigations involving procurement integrity issues, conflicts of interest, billing and cost concerns, grant compliance and small business program allegations, and proactively advising clients on how to manage any risk
preparing voluntary and mandatory disclosures and interacting with contracting officers, agency counsel and other agency officials
counseling clients on responding to show-cause letters, notices of proposed suspension or debarment, and preparing submissions demonstrating present responsibility, mitigating factors and internal control improvements to agency suspending and debarring officials