1. Home
  2. |Professionals
  3. |Amy Laderberg O'Sullivan

Amy Laderberg O'Sullivan

Partner
Partner
YW9zdWxsaXZhbkBjcm93ZWxsLmNvbQ==
VCard
VCard

Areas of Focus

Overview

In quickfire bid protest litigation where a company’s must-win contracts are on the line, Amy O’Sullivan has earned a reputation for her responsiveness, quick absorption of information, and nimbleness in working with companies of all sizes and levels of experience as government contractors. She blends her well-rounded procurement knowledge with her niche experience of the full range of small-business issues with successful outcomes, earning the trust of clients even when litigating subject to the informational sharing limitations of protective orders. Amy also extends her practice to include investigations, mergers and acquisitions, and counseling, particularly on matters involving the complex U.S. Small Business Administration requirements and compliance.

Amy has litigated extensively, with well over 100 bid and size protests throughout her career, before the Government Accountability Office, the Court of Federal Claims, and the SBA’s Office of Hearings and Appeals. As protester or intervenor, these matters range from procurements worth billions of dollars to small 8(a) set-aside competitions and involve all substantive issues, including complex cost evaluation challenges working with support from consultants, unique technical issues, and investigative support associated with organizational conflicts of interest.

Amy’s counseling practice ranges from the day-to-day survival issues facing small businesses to the complex and specific legal questions from large defense contractors. She regularly works on the unique issues confronting small businesses as well as those arising in connection with teaming and contracting with them, including navigating the SBA’s regulations in such areas as affiliation; limitations on subcontracting; the mentor-protege program; the Small Business Innovation Research program; small business, 8(a), Alaska Native corporation, women-owned small business, and service-disabled veteran-owned small business status issues; and the Paycheck Protection Program. She reviews and negotiates terms of subcontracts, teaming agreements, mentor-protege agreements, and joint venture agreements.

Amy has also assumed numerous roles in connection with the mergers or acquisitions of government contractors, including conducting due diligence reviews, compliance with SBA notice and approval requirements, preparing/negotiating government contracts’ specific representations and disclosure schedules, and handling the novation of contracts. She has led internal investigations of potential civil and criminal matters for major corporations and assisted in disclosures to various government agencies. Amy has counseled clients on establishing, enforcing, and maintaining overall compliance programs. She has provided on-site training for companies for a range of issues, including contracting with small businesses, ethics and compliance, and the basics of government contracting. She has also served as a course instructor for Federal Publications Seminars for a number of topics, including bid protests, past performance, the basics of government contracting, cost-reimbursement contracting, and A-76 procurements.

Amy has been named one of the top lawyers in the government contracts field by Chambers USA. She is an Acritas Star, an Acritas Independently Rated Lawyer, and a fellow of the American Bar Foundation. In 2017, she was included in Law360’s list of “Government Contract MVPs.”

Amy received her B.A. with honors in art history and political science from Williams College in 1996, where she was also a member of the swimming, water polo, and rugby teams. She graduated from William & Mary School of Law in 1999, where she served as notes editor of the William & Mary Law Review and articles editor of the William & Mary Journal of Women and the Law.

Prior to joining Crowell & Moring, Amy clerked for the Hon. Jerome B. Friedman of the U.S. District Court for the Eastern District of Virginia.

Amy is a member of the bars of the District of Columbia, the state of Virginia, the U.S. District Court for the Eastern District of Virginia, and the U.S. Court of Appeals for the Fourth Circuit.

Career & Education

    • College of William & Mary Marshall-Wythe School of Law, J.D., 1999
      William & Mary Law Review: notes editor
      William & Mary Journal of Women and the Law: articles editor
    • Williams College, B.A., honors, art history and political science, 1996
    • College of William & Mary Marshall-Wythe School of Law, J.D., 1999
      William & Mary Law Review: notes editor
      William & Mary Journal of Women and the Law: articles editor
    • Williams College, B.A., honors, art history and political science, 1996

    • District of Columbia
    • Virginia
    • U.S. District Court for the Eastern District of Virginia
    • U.S. Court of Appeals for the Federal Circuit
    • U.S. Court of Appeals for the Fourth Circuit
    • U.S. Court of Federal Claims
    • District of Columbia
    • Virginia
    • U.S. District Court for the Eastern District of Virginia
    • U.S. Court of Appeals for the Federal Circuit
    • U.S. Court of Appeals for the Fourth Circuit
    • U.S. Court of Federal Claims
Amy is extremely responsive, organized, and detail-oriented. She is a very sharp lawyer who is great at advising our business teams as they make challenging protest decisions. We value her insight, intelligence, and strategic thinking. She is excellent at bid protests.

— Chambers USA, 2022

Amy's Insights

Client Alert | 4 min read | 07.08.25

GAO Moves the Goalposts: New Post-Debriefing Timeliness Trap for Protesters

The deadlines for filing a GAO protest are short and strictly enforced.  In post-award protests, the general rule is that a company must file its protest within ten days of when the protester knows, or should have known, of its basis of protest.  However, GAO’s regulations provide an exception to this rule for “protests challenging a procurement conducted on the basis of competitive proposals under which a debriefing is requested and, when requested, is required”—in such a situation, “[the] protest shall not be filed before the debriefing date offered to the protester, but shall be filed not later than 10 days after the date on which the debriefing is held.”  4 CFR §21.2(a)(2)....

View All Insights

Representative Matters

RECENT REPRESENTATIVE BID PROTESTS

Recent representative protests include:

  • Successfully challenged U.S. Department of Labor award of an approximately $100 million contract for operation of the Los Angeles Job Corps Center based on unequal discussions associated with revisions to proposed key personnel. YWCA of Greater Los Angeles, B-414596 et al., July 24, 2017, 2017 CPD ¶ 245.
  • Obtained a recommendation that the agency reimburse a protester for costs of filing and pursuing a protest challenging the agency’s implementation of corrective action where the agency unduly delayed taking corrective action in response to a meritorious challenge that the Department of the Army failed to evaluate proposals using a common baseline. TRAX International Corporation—Costs, B-410441.8, Aug. 17, 2016, 2016 CPD ¶ 226.
  • Successfully challenged offeror’s exclusion from the competitive range for the Department of Justice’s investigative support services for the asset forfeiture program. Arctic Slope Mission Services, LLC, B-410992.5, B-410992.6, Jan. 8, 2016, 2016 CPD ¶ 39.
  • In corrective action protest in connection with a $700 million U.S. Army Corps of Engineers procurement for the permanent canal closures and pumps for New Orleans, successfully obtained a finding from the Court of Federal Claims that the GAO decision was, in part, irrational. CBY Design Builders v. United States, 102 Fed. Cl. 303 (2012).

Recent representations on behalf of contract awardees and offerors retained in the competitive range include:

  • Successfully defended an award by the Social Security Administration for support services for the agency’s folder storage operation at the National Records Center against two challenges before GAO. Eagle Eye Electric, LLC, B-415562, B-415562.3, Jan. 18, 2018, 2018 CPD ¶ 33; Dextera Corporation, B-415562.2, B-415562.4, Feb 5, 2018, 2018 CPD ¶ 66. Successfully defended the same award before the Court of Federal Claims. Eagle Eye Electric, LLC v. United States, No. 18-173C (Fed. Cl. May 31, 2018).
  • Successfully defended a $300 million award by Customs and Border Protection for data center support services from multiple organizational conflict of interest challenges. IBM Corporation, B-415575, Jan. 19, 2018, 2018 CPD ¶ 61. 
  • Successfully argued for the dismissal of the entirety of a protest before GAO of an award for base operation and support for certain Marine Corps facilities on the basis of lack of interested party status.
  • Successfully defended a $185 million award by the National Aeronautics and Space Administration for the provision of various information technology services for the John F. Kennedy Space Center. AbacusSecure, LLC, B-415175, B-415175.2, B-415175.3, B-415175.4, Dec. 6, 2017, 2017 CPD ¶ 375.
  • Successfully defended an 8(a) sole source award by the Defense Intelligence Agency for approximately $20 million for facility support services from a challenge that the Small Business Administration improperly accepted the requirement into the 8(a) program. SKC, LLC, B-415151, Nov. 20, 2017, 2017 CPD ¶ 366.
  • Successfully defended an award by the National Nuclear Security Administration for services in support of the Office of Personnel and Facility Clearances at Kirtland Air Force Base from challenges to the agency’s evaluation under the cost and non-cost factors as well as to the conduct of discussions. Synergy Solutions, Inc., B-413974.3, June 15, 2017, 2017 CPD ¶ 332.
  • Successfully defended protest of award by the Department of the Air Force following corrective action upholding award of a 10-year, $200 million contract for aerospace systems technical research and operations services (ASTROS) at Edwards Air Force Base, California. Jacobs Technology, Inc., B-413389.3, B-413389.4, Jul. 21, 2017, 2017 CPD 244.
  • Successfully defended protest at GAO challenging the Department of Energy, National Nuclear Security Administration’s award of services for the implementation of DOE’s Personnel Security Program. Synergy Solutions, Inc., B-413974.3, June 15, 2017, 2017
    CPD ¶ __.
  • Successfully defended protests challenging more than $58 billion worth of U.S. Department of Defense projects for Tricare “managed care support” contracts. UnitedHealth Military & Veterans Services, LLC; WellPoint Military Care Corporation; Health Net Federal Services, LLC, B-411837.2 et al., Nov. 9, 2016, 2016 CPD ¶ 329.
  • Successfully defended the award of a $285 million task order issued by the Department of Veterans Affairs for help desk services. Systems Made Simple, Inc., B-412948.2, Jul. 20, 2016, 2016 CPD ¶ 207.
  • Successfully defended National Aeronautics and Space Administration’s $200 million award for software engineering services. Systems Engineering Partners, LLC, B-412329, et al., Jan. 20, 2016, 2016 CPD ¶ 31.
  • Successfully defended award of contract for test support services for the U.S. Army Operational Test Command at Fort Hood, Texas. Research Analysis & Maintenance, Inc., B-410570.6, et al., Jul. 22, 2015, 2015 CPD ¶ 239.
  • Successfully defended GAO and COFC protests and Federal Circuit Appeal of protest of an Army award of a contract to manage two Family Health Centers in Virginia, defeating allegations of improper organizational conflicts of interest, improper discussions, and numerous evaluation challenges. CRAssociates, Inc. v. U.S., 102 Fed. Cl. 698 (2011), appeal denied per curiam at 475 Fed. Appx. 341 (Fed. Cir. Aug. 14, 2012).
  • Successfully defend an award valued up to $229 million for information technology services against wide-ranging challenges to the National Aeronautics and Space Administration’s evaluation proposals of price, technical, and past performance proposals as well as the agency’s conduct during discussions. DB Consulting Group, Inc., B-401543.2, B-401543.3, Apr. 28, 2010, 2010 CPD ¶ 109.

Amy's Insights

Client Alert | 4 min read | 07.08.25

GAO Moves the Goalposts: New Post-Debriefing Timeliness Trap for Protesters

The deadlines for filing a GAO protest are short and strictly enforced.  In post-award protests, the general rule is that a company must file its protest within ten days of when the protester knows, or should have known, of its basis of protest.  However, GAO’s regulations provide an exception to this rule for “protests challenging a procurement conducted on the basis of competitive proposals under which a debriefing is requested and, when requested, is required”—in such a situation, “[the] protest shall not be filed before the debriefing date offered to the protester, but shall be filed not later than 10 days after the date on which the debriefing is held.”  4 CFR §21.2(a)(2)....

View All Insights

Insights

Client Alert | 4 min read | 07.08.25

GAO Moves the Goalposts: New Post-Debriefing Timeliness Trap for Protesters

Firm News | 11 min read | 06.05.25

Crowell Attains Leading Rankings in Chambers USA 2025

Client Alert | 1 min read | 06.02.25

Job Corps Centers: Widespread Contract Terminations due to Agency’s “Pause”

Speaking Engagement | 05.13.25

"Bid Protests: Strategies to Secure Your Piece of the Smaller Contract Pie," OOPS 2025: Government Contractors Reacting and Adapting to the New Administration, Tyson's Corner, VA.

View All Insights

Practices

Amy's Insights

Client Alert | 4 min read | 07.08.25

GAO Moves the Goalposts: New Post-Debriefing Timeliness Trap for Protesters

The deadlines for filing a GAO protest are short and strictly enforced.  In post-award protests, the general rule is that a company must file its protest within ten days of when the protester knows, or should have known, of its basis of protest.  However, GAO’s regulations provide an exception to this rule for “protests challenging a procurement conducted on the basis of competitive proposals under which a debriefing is requested and, when requested, is required”—in such a situation, “[the] protest shall not be filed before the debriefing date offered to the protester, but shall be filed not later than 10 days after the date on which the debriefing is held.”  4 CFR §21.2(a)(2)....

View All Insights