Patrick A Costello - Dailey, LLP Attorney

Jacqueline M. Woolley / Attorney

Practice Areas: Employment Law

When workplace conflicts occur, my job is to help employers manage those conflicts so that they do not become more disruptive than they need to be.

Most attorneys who work in labor and employment law only represent employees or employers, but Jackie Woolley takes an uncommon approach to her practice. She has more than twenty-five years of experience in employment law. For the past fifteen years, she has both supported employees who have needed a knowledgeable advocate and helped employers manage their day-to-day personnel matters. Her hybrid model allows her to examine and understand labor and employment issues from both sides, which affords her clients exceptional representation.

Jackie spends much of her time advising and partnering with her employer clients to address personnel matters and problems. For many clients, she serves as both out-house employment counsel and HR department. Her responsibilities include ensuring compliance with employment laws, improving employee hiring, managing discipline and termination processes, responding to accommodation requests, conducting trainings and internal investigations, and drafting and enforcing personnel policies and employee contracts and agreements. One of her primary goals is to foster positive working relationships between employers and their employees.

The remainder of Jackie’s practice is dedicated to counseling employee clients who have experienced on-the-job discrimination, harassment, or retaliation. She also advises clients on the terms and conditions of their employment, from hiring through separation. Additionally, Jackie drafts and negotiates executive agreements and separation packages, advises employees on leave and reasonable accommodation issues, and resolves wage and hour matters. She litigates some of those cases through the administrative-agency process, in alternative dispute resolution forums and/or in court, but her goal—whenever possible—is to resolve work disputes amicably so as to avoid costly litigation.

Jackie followed her father into the practice of law and, like him, clerked for the Honorable Louis C. Bechtle, former Chief Judge Emeritus for the United States District Court for the Eastern District of Pennsylvania. Since her clerkship, she has worked with several prominent Philadelphia-area law firms, including both an Am Law 100 firm and an employment law boutique firm.

Beyond Dailey

In her free time, Jackie loves nothing more than spending time with her “young adult” children, her husband, and her many extended family members and friends. Jackie is also passionate about promoting literacy in underserved communities throughout the country. She proudly serves as a board member of the Children’s Literacy Initiative, a national non-profit whose mission is to create powerful readers, writers, and thinkers and to give Black and Latinx children the high-quality education they deserve and need to thrive.

Representative Matters

Employer Matters

  • Defended a client against a former employee’s race discrimination and retaliation claim and negotiated an early-in-litigation, de minimis settlement
  • Conducted a workplace investigation after a former employee alleged a hostile work environment based on her gender
  • Prepared personnel policies and onboarding and separation templates and conducted workplace trainings for multi-state employer

Employee Matters

  • Negotiated favorable terms and conditions of separation for an executive after a change in company leadership
  • Arranged amicable pre-litigation settlement terms for a woman who asserted that her discharge was motivated by her gender
  • Guided an employee through an HR complaint and investigation related to her age discrimination and retaliation claim

Bar Admissions

  • Pennsylvania
  • New Jersey

Federal Court Admissions

  • U.S. Court of Appeals for the Third Circuit
  • U.S. District Court for the Eastern District of Pennsylvania
  • U.S. District Court for the Middle District of Pennsylvania
  • U.S. District Court for the District of New Jersey


  • Temple University Beasley School of Law, Juris Doctor, 1993
  • University of Richmond, Bachelor of Arts, 1990


  • Member, Board of Directors, Children’s Literacy Initiative, 2017- present
  • President, Norwood-Fontbonne Academy Parents’ Association, 2005-2006; 2013-2014