Photo of Heather A. Bailey

Heather A. Bailey



The John Marshall Law School, J.D., 2001  

Bowling Green State University, B.A., 1992



Heather credits her experience working full-time in office administration and human resources during law school for her seamless transition into management-side labor and employment law. The skills she developed as a legal secretary and office manager help strengthen her appreciation and understanding of clients’ concerns today and gave her the tools to be efficient, respectful and meticulous in her role as an attorney.

For 20 years, Heather has concentrated her practice in employment and labor counseling and litigation, including discrimination and trade secret / non-compete lawsuits, FLSA class actions, labor negotiations and arbitrations, affirmative action, OFCCP/DOL audits and FINRA issues. She counsels on day-to-day operations, human resources, and management decisions regarding employees, practices and policies. Heather also works comfortably with FMLA/ADA, sexual harassment, affirmative action, union avoidance and other types of employee and management training. Her clients operate across the U.S. in industries like vending, healthcare, transportation, parking, automotive repair, construction, staffing, hospitality (restaurants/taverns), banking, nonprofits, IT, and manufacturing to name a few.

A thought leader in the labor and employment industry, Heather regularly contributes to the firm’s Labor & Employment Law Update, the vending industry’s National Automatic Merchandising Association, Vending Times and Vending Market Watch quarterly publications, and the Illinois Chamber of Commerce’s human resources advisory blog. She co-authored the 2019 Illinois Chamber of Commerce’s Illinois Employment Law Handbook, and frequently presents at the Illinois Institute for Continuing Legal Education, Clear Law Institute, Chicago Bar Association, Lorman Education Services and NAMA-related conventions across the U.S.

As a prior co-chair of the firm’s Committee for Diversity and Inclusion, Heather managed a team charged with not only creating diversity awareness within the firm and its clients, but also executing strategies to recruit, retain and mentor attorneys and staff of all backgrounds. Additionally, Heather provides incomparable leadership to the firm’s younger attorneys; taking the time to mentor them and help them to develop into exceptional attorneys. 


  • 2015 Chicago Business Journal Women of Influence Honoree
  • Recognized as a Pro to Know by Automatic Merchandiser and VendingMarketWatch: 2015
  • Selected to the Illinois Super Lawyers list: 2014, 2015, 2016, 2017, 2018, 2019, 2020, 2021
  • Received Lawyer Monthly Women in Law Award, USA: 2018 

Memberships & Involvement

  • Professional Women’s Club of Chicago: Immediate Past President, 2016-2017; President, 2015-2016; Vice President, 2014-2015; Communications Committee Co-chair, 2012-2014; Communications Committee Co-Chair Board Member, 2012-2014 
  • Executive Committee Member: ProVisors, 2017-Present
  • Advisory Council: Illinois Restaurant Association, 2020, 2021, 2022
  • Member: National Automatic Merchandising Association (NAMA) (Employment/Labor Knowledge Source Partner since 2003)
  • Member: Illinois Chamber of Commerce (Employment Legislation Advisor)
  • Member: Former Co-chair; SmithAmundsen Committee for Diversity and Inclusion
  • Member: Defense Research Institute (DRI); American Bar Association; Chicago Bar Association; Illinois Association of Defense Trial Counsel
  • Volunteer/ Co-captain: Special Olympics Chicago, Polar Plunge Fundraiser, 2008-2022
  • Volunteer: The Youth Campus, 2004–2011
  • Volunteer: Children’s Home + Aid, 2012-2014


  • Secured a dismissal for an employer at the Chicago Commission on Human Relations with a Motion to Dismiss, arguing the IHRA does not apply to independent contractors.
  • Won Summary Judgment in the S.D. of Florida for a vending operator that the Motor Carrier Act Exemption of the FLSA applies to vending route drivers.  This defeated that route drivers were entitled to any overtime pay.
  • Filed an amicus brief in the Middle District of Tennessee for a vending operator on the Motor Carrier Act Exemption where the judge reversed the grant of summary judgment for the plaintiff.
  • Won a post-trial motion where the original verdict was $1 million and argued it was punitive and the IHRA does not allow for punitive verdicts/damages. The judge agreed and remitted the verdict down to $175,000.
  • Won Summary Judgment in a race discrimination case under IHRA and Title VII in Cook County.
  • Obtained a motion to dismiss with prejudice for claims of breach of employment contract, defamation and infliction of emotional distress on behalf of an employer.
  • Won Summary Judgement on a national origin discrimination complaint in the Northern District of Illinois.
  • Successfully assisted a group of employees from de-certifying their union representation with a grocery store chain.
  • Won a Motion to Dismiss in a common law retaliatory discharge case under the Workers’ Compensation Act after arguing that the complaint failed to state a claim entitling the plaintiff to recover because the plaintiff was never discharged from her job. The court found that the plaintiff failed to show she was terminated from her position. The dismissal was upheld in the 4th District Appellate Court.

News & Press Releases


Contributing Author, SmithAmundsen's Labor & Employment Law Update, a labor and employment advisory blog.

Contributing Author, Illinois Chamber of Commerce's Chamber Dispatch, an HR advisory blog.


Presentations & Events