Karen A. Whitley - a Boston, United States Business Litigation Lawyer

Boston Business Litigation Lawyer

Updated: 03/16/2026

Areas of Practice

Business Litigation
Labor & Employment

Attorney Information

Overview

Karen serves on the firm’s Management Committee as the ‘At Large’ member for Boston. She is also a member of the firm’s Labor & Employment and Litigation Practice Groups. Karen focuses her practice on management-side employment litigation and counseling, including discrimination, wage and hour, and restrictive covenant proceedings. She values working closely with HR professionals and in-house counsel to develop a practical business approach to thorny employment law issues. Karen advises employers on legal compliance in all phases of the employment relationship, conducts sensitive internal investigations, and provides proactive training to management and staff on cutting edge issues. She provides employment law advice arising in connection with mergers and acquisitions, and helps employers protect their proprietary data through the enforcement of restrictive covenants and other policies.

Karen maintains an active practice before anti-discrimination agencies and trial courts on behalf of private employers in the banking, insurance, recruiting, education, hospitality, manufacturing, and pharmaceutical industries. She has been a trusted advisor to small start-up businesses, mid-size organizations, and multi-national companies to ensure adherence with numerous federal and state laws, including the FLSA, ADA, ACA, FMLA, WARN Act, COBRA and similar state laws.

Prior to joining the firm in 2014, Karen was a partner at Jones Day in Boston for 4 years. Previously, Karen was with Hanify & King in Boston for 16 years. Karen began her legal career as a Law Clerk to the Justices of the Superior Court of Massachusetts.

Key Cases:

Represented employer in federal court action where former employee claimed violation of USERRA and Massachusetts anti-discrimination laws following his return from active duty deployment.
Represented Australian company in matter filed by former executive seeking sales commissions and other compensation.
Defended multi-national insurance company against claim for severance under “Good Reason” provision in Employment Agreement.
Defended national flooring company in class action litigation asserting workers were misclassified as independent contractors.
Defended restaurant and event venue in class action by workers for violation of the Massachusetts Tip Act.
Conducted sensitive sexual harassment investigation involving co-owners of media business leading to favorable settlement of threatened litigation.
Assisted non-profit organization with notice and severance documentation following significant restructuring including closure of offices in multiple states.
Developed three tiers of employment agreements and related documents for over 900 employees in 20 states as part of acquisition of competitor’s business by national company.
Assisted multiple employers with drafting and implementation of Massachusetts Sick Leave policies in compressed timeframe.
Counseled employers on coverage and reporting obligations under the Affordable Care Act.
Annually review, revise and update employee handbooks for more than 20 employers, ranging in size from 10 employees to more than 200 employees with operations in Massachusetts and New Hampshire.

Awards and Honors

Super Lawyers® Selectees

Karen A. Whitley included in a Super Lawyers® list

Honors

Massachusetts Super Lawyer®, Employment & Labor Law
Best Lawyers in America®, Litigation - Labor and Employment
Top Women of Law, Massachusetts Lawyers Weekly in 2015
2021 Deane Laycock Award, The Boston Club

Other Sources of Feedback About Karen A. Whitley

Included on the 2026 Massachusetts Super Lawyers list

Past Lists

2025 Massachusetts Super Lawyers list
2024 Massachusetts Super Lawyers list
2023 Massachusetts Super Lawyers list
2022 Massachusetts Super Lawyers list
2021 Massachusetts Super Lawyers list
2020 Massachusetts Super Lawyers list
2019 Massachusetts Super Lawyers list
2018 Massachusetts Super Lawyers list
2017 Massachusetts Super Lawyers list
2016 Massachusetts Super Lawyers list
2015 Massachusetts Super Lawyers list
2014 Massachusetts Super Lawyers list
2013 Massachusetts Super Lawyers list
2012 Massachusetts Super Lawyers list
2011 Massachusetts Super Lawyers list

Education

Legal Education
- Boston College Law School, Boston, Massachusetts, 1993
  J.D.
Non Legal Education
- Wellesley College, 1990
  B.A.
  Honors: magna cum laude

Current Employment Position(s)

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Shareholder
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Past Positions

Associate Justices of the Superior Court of Massachusetts, Law Clerk, 1993 - 1994

Pro Bono Activities

Secretary of the Board and Member of the Executive Committee, The Boston Club
Ambassador, Governance Committee, and Membership Committee Member, The Boston Club
Board Member, Wellesley College Alumnae Association
Chair, Wellesley College Alumnae Achievement Award Selection Committee
Seven-time walker in the Avon Walk to End Breast Cancer (Boston, Charlotte and Washington DC)
20-year Member, Wellesley Lawyers Network
Former Advisory Board Member for Education & Training Branch, Greater Boston YMCA; In-School Mentor, Big Sister Association; President of the Wellesley College Alumnae of Boston; Member of the Executive Women's Golf Association
Member of ProVisors

Published Works

Articles

Keeping the “Independent” in an Independent Contractor Relationship
Clarifying the Undue Hardship Standard in Response to Requests for Reasonable Accommodation (p25)
Clarifying the undue hardship standard in response to requests for reasonable accommodation
The New FFCRA Regulations: Helpful Clarifications, a Few Surprising Answers
What Employers Need to Know About the Families First Coronavirus Response Act
New Hampshire Workplace Legal Developments
NH Legal Perspective: Keep your employee handbook up to date
Check your employee handbook: Changes in laws greater awareness among employees mean the time has come to consider an update
NH Legal Perspectives: EEOC’s wellness incentive rules run off the track
NH Legal Perspective: Consistency still key in Family and Medical Leave Act interference claims
Dress Codes and Discrimination – Motive the key in Abercrombie Supreme Court case

Bar Admissions

Massachusetts
New Hampshire

Other Affiliations

Boston Bar Association's Labor and Employment Section

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Contact

Boston, MA

28 State Street
22nd Floor
Boston, MA 02109

Directions

Phone: 603-945-9922

Fax: 617-439-9363

Email: Send a message

Website: https://www.sheehan.com/

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Karen A. Whitley - Boston, MA