Recognized by Massachusetts Lawyers Weekly as one of 2021’s Lawyers of the Year, Hillary has exclusively represented employees for over 15 years and has helped recover millions of dollars in damages for workers in Massachusetts and throughout the United States. 

Hillary started Fair Work P.C. with her friend and colleague Steve Churchill in 2013. Before that, she was a partner at another nationally-recognized employment firm where she helped pioneer litigation concerning the misappropriation of employees’ tips in the food and customer service industry. Earlier in her career, Hillary served as a Blackmun Fellow at the Center for Reproductive Rights in New York and spent several years in Wisconsin representing victims of domestic violence in rural communities before joining the Environmental Protection Unit as an Assistant Attorney General at the Wisconsin Department of Justice. 

Since going into private practice, Hillary has successfully litigated dozens of class actions on behalf of thousands of employees against all sorts of companies for their illegal employment practices. She has pursued cases alleging failure to pay wages and overtime; failure to correctly classify workers as employees, rather than as independent contractors; failure to pay wages for all time worked; and for illegal wage deductions and withholdings. In one such case, Montoya v. CRST Expedited, Inc., she recovered more than $12 million for long-haul truck drivers who were not properly paid for training time, had improper deductions taken from their wages, and were not paid for all hours worked.

In addition to her class action practice, Hillary has represented numerous individuals on claims for whistleblower retaliation and discrimination. In 2009, she helped obtain a six-figure jury verdict plus reinstatement for a client who claimed he had been unlawfully removed from his position as head of the Stoughton Police Department’s detective division. She also represented an individual who had been denied a position with the U.S. Foreign Service because of her diabetes. On the eve of trial, the State Department agreed to a settlement in which it paid her attorneys’ fees and lost wages and hired her for a position with the Foreign Service.

Hillary has pursued appeals before the Massachusetts Appeals Court, the Massachusetts Supreme Judicial Court, and the United States First Circuit Court of Appeals. In 2019, she successfully defeated an appeal by a truck company to the United States Supreme Court, New Prime, Inc. v. Oliveira. The company in that case argued that the plaintiff could not pursue a class action based on an arbitration agreement he signed. The Supreme Court rejected that argument, ruling unanimously that the arbitration agreement was not enforceable under the Federal Arbitration Act.

In 2008, Massachusetts Lawyers Weekly named Hillary an “Up and Coming Lawyer,” an award that recognizes attorneys who have been licensed for less than 10 years but who have already distinguished themselves in their field. Massachusetts Lawyers Weekly has also rated Hillary a “Super Lawyer” every year since 2013. In 2019, it named her of its “Top Women of Law,” an award that recognizes exceptional and pioneering female lawyers working in Massachusetts.

In 2014, Hillary successfully ran all 26.2 miles of the Boston Marathon on behalf of Casa Myrna, Boston’s largest provider of shelter and supportive services to survivors of domestic violence. When she’s not working, she spends as much time as possible at the beach and will swim anywhere along New England’s Atlantic coast pretty much any time between May and October.


Columbia Law School J.D. - 1999

Brown University A.B. - 1995

Bar Admissions

DeWeese-Boyd v. Gordon College, 487 Mass. 31 (2021) (Supreme Judicial Court ruling that associate professor at Christian college was not exempt from discrimination protection laws as a "ministerial" employee)

Montoya v. CRST Expedited, Inc., 2020 WL 2850235 (2020) (issuing preliminary injunction to prevent long-haul trucking company from continuing to engage in unfair, deceptive, and coercive practices)

New Prime, Inc. v. Oliveira, 139 S.Ct. 532 (2019) (U.S. Supreme Court ruling that truck drivers were exempt from Federal Arbitration Act as workers engaged in "interstate commerce")

Montoya v. CRST Expedited, Inc., 404 F. Supp. 3d 364 (2019) (granting summary judgment against long-haul trucking company on claims for unpaid work-time and fraudulent driver training practices)

Montoya v. CRST Expedited, Inc., 311 F. Supp. 3d 411 (2019) (certifying class of truck drivers in case alleging violations of employee and consumer protection laws)

Lichy v. Centerline Communications LLC, 2018 WL 1524534 (D. Mass. 2018) (conditionally certifying FLSA class of telecommunication technicians on claim for unpaid work time)

Cormier v. Landry's Seafood House-North Carolina, Inc., 2015 WL 12732419 (D. Mass. 2015) (granting partial summary judgment in favor of plaintiff wait staff employees on improper tip pooling claim)

Bednark v. Catania Hospitality Group, Inc., 78 Mass. App. Ct. 806 (2011) (Appeals Court ruling reversing judgment for hotel on claim that it reasonable patrons may consider an 18-19 percent "administrative fee" to be a gratuity or service charge for banquet wait staff)

DiFiore v. American Airlines, Inc., 454 Mass. 486 (2009) (Supreme Judicial Court ruling that airline could be held liable under state law protecting employees' tips despite not directly employing the plaintiffs)

Panelist, "Using Consumer Laws to Protect Workers from Corporate Fraud and Misconduct," National Consumer Law Center, July 28, 2021

Faculty, "47th Annual Robert Fuchs Labor Law Conference," Massachusetts Bar Association, February 11, 2021

Panelist, "Massachusetts Wage Act: Treble Your Knowledge," Massachusetts Bar Association, July 27, 2020

Presenter on Finding your Voice in Conflict – Strategies for Dispute Resolution in all Aspects in Life, Women Awakening, December 2017

Faculty speaker on panel concerning tip pooling, Bridgeport Continuing Legal Education, June 2017

Panelist, "Reinventing Motion Practice to Win," Precision Advocacy, May 2017

Speaker on panel concerning developments in wage and hour litigation, discrimination, collective actions, and private settlements, JAMS / Mass Lawyers Weekly, October 2017

Faculty, "Robert Fuchs Labor Law Conference: Government and the Bar Confront the Fissured Workplace," Massachusetts Bar Association, October 2015

Panelist, "Nuts and Bolts of Employment Law Class and Collective Actions," Massachusetts Continuing Legal Education, December 2014

Speaker on panel concerning recent Supreme Judicial Court wage decisions, Boston Bar Association, October 2011

Lawyer of the Year, Massachusetts Lawyers Weekly (2021)

Top Women of Law, Massachusetts Lawyers Weekly (2019)

Super Lawyer, Massachusetts Lawyers Weekly (2013 - Present)

Up and Coming Lawyer, Massachusetts Lawyers Weekly (2008)

National Lawyers Guild

NARAL Pro-Choice Massachusetts


New York


United States Supreme Court

United States Court of Appeals, First Circuit

District of Massachusetts

News + Developments

Find out what's up at Fair Work.

Let's Talk

Think you have a case? Get in touch!