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Tamsin R. Kaplan

phone: 617-589-3892
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Tamsin is an employment lawyer and business litigator, and serves as outside general counsel to diverse nonprofits and private schools. She has extensive experience representing businesses, executives and other high-level professionals in a full range of employment-related issues from recruitment through termination. Tamsin frequently conducts workplace investigations, provides trainings on diversity and harassment, and advises employers regarding employee handbooks, employment audits, and workplace policies and practices. She regularly litigates cases involving employment and business disputes before federal and state courts and agencies.

  • Successfully represented a defendant higher education institution executive and officer on a motion to dismiss in a federal class action suit claiming breach of contract and fiduciary duty, among other claims. Prevailed on appeal in the First Circuit Court of Appeals.
  • Successfully enforced a non-compete agreement against a former high level employee in the medical services industry.
  • Successfully defended a high tech company against allegations of unpaid wages and employment discrimination.
  • Won a judgment for a company co-founder in a lawsuit arising from the breakup of a business, including breach of contract and non-compete claims.
  • Negotiated numerous CEO, CFO and CMO employment, non-compete and severance agreements.
  • Defeated a summary judgment motion in the Superior Court Business Litigation Session in a lawsuit involving equity distribution in a biotech start-up.
  • Successfully defended a medical practice in a breach of contract lawsuit by a physician.
  • Won a five figure discovery sanction against the opposing party in a Superior Court lawsuit.
  • Conducted an investigation of allegations against a high level town official.
  • Obtained a high six figure settlement for a health care executive by commencing arbitration to enforce the good reason termination provision in the client’s employment contract.
  • Prevailed on a motion to dismiss claims against a non-profit executive in U.S. District Court.


  • Selected a “Top Woman of Law” by Massachusetts Lawyers Weekly, 2019
  • Selected Chambers USA Leading Lawyer 2013-2014; Recognized Practitioner 2015-2019
  • Best Lawyers in America©, 2014-2021
  • Massachusetts Super Lawyers, 2009-2020 (Top 50 Women Massachusetts Super Lawyers, 2013-2016; Top 100 New England Super Lawyers, 2014; Top 50 Women New England Super Lawyers, 2014; and Top 100 Massachusetts Super Lawyers, 2014)


  • Massachusetts
  • United States Supreme Court
  • United States Court of Appeals for the First Circuit
  • United States District Court for the District of Massachusetts
  • Supreme Judicial Court, Commonwealth of Massachusetts


  • American Bar Association
  • Boston Bar Association
  • Massachusetts Bar Association (Business Law Section Council, 2012-2017)
  • Women’s Bar Association (Board Member, 2009-2015; Middlesex Committee, 1995-2012; Business Development Committee, 2009-2015)
  • International Lawyers Network


  • American Arbitration Association Expedited Commercial Panel

Massachusetts Continuing Legal Education:

  • Labor and Employment Curriculum Advisory Committee (2010-present)

In her downtime, Tamsin enjoys sculling on the Charles River, Pilates, swimming or relaxing on the beach in Sarasota. She is an award-winning comedian who earned the title of “Funniest Lawyer in Massachusetts” for her stand-up comedy at a 2014 event to benefit the Women’s Bar Foundation.

News & Insights

4 Ways HR Can Create and Maintain Inclusive Workplaces, authored article for Human Resource Executive

41st Annual Labor & Employment Conference, panelist at Massachusetts Bar Association event

Time Off For Veterans Under the BRAVE Act (0:01:14), speaker at 2019 Employment Law Seminar

Employee Handbooks: Benefits, Pitfalls and Preserving At-Will Employment, authored article in Cannabis Business Executive

Sexual Harassment in the Workplace (0:17:17), speaker at 2018 Employment Law Seminar

Employment Challenges and Solutions for the Cannabis Industry, presenter at Cannabis World Congress & Business Exposition

Workplace Investigations & Confidentiality (5:58), speaker at 2017 Employment Law Seminar

Social Media & Related Policies (10:48), speaker at 2017 Employment Law Seminar

Mentors for Rainmaking, panelist for Women's Bar Association Business Development Committee program

Developments in Trial Practice and New Procedural Rules, presenter at MCLE's 19th Annual Employment Law Conference

Maintaining Employee Personnel Records (14:31), speaker at 2016 Employment Law Seminar

Misclassifying Employees as Independent Contractors (1:55), speaker at 2016 Employment Law Seminar

Diversity, Unconscious Bias and Employer Liability, speaker at CUPA-HR Eastern Region Conference

Mass.: First Workplace Medical Marijuana Lawsuit Filed, quoted by the Society for Human Resource Management (SHRM)

Can worker fired for pot use sue?, quoted in Massachusetts Lawyers Weekly

For employers, time to review drug-testing policies, authored article in New England In-House

Pregnant Workers: What Are Employers’ Obligations? (7:32), speaker at 2015 Employment Law Seminar

Employment Law Seminar Q&A (8:51), speaker at 2015 Employment Law Seminar

Rights for Domestic Workers (4:16), speaker at 2015 Employment Law Seminar

Employment Law Fundamentals: Get Smart or Get Sued®, chair of Social Law Library program

Employment Law Essentials, presenter for The Lenny Zakim Fund

Learning and Networking with Alumni & Practitioners, panelist at Boston College Law School Boot Camp event

 2014 Employment Law Seminar (1:28:53), speaker at 2014 Employment Law Seminar

Social Media: Current Issues Facing Employers (17:18), speaker at 2014 Employment Law Seminar

Non-Competition Agreements: Are They Facing Possible Extinction?, author of article in Corporate LiveWire's Expert Guide: Labor & Employment Law 2014

What Really Happened? Investigating Workplace Discrimination and Harassment Complaints, panelist at American Arbitration Association's national webinar

Lifecycle of a Business: Part III Employment & Business Litigation Matters, presenter at Massachusetts Bar Association program

Finding Your Fit-Discovering Your Niche in the Marketplace, moderator at Boston Product Management Association career night event

What Every Employer Should Know, presenter for The Lenny Zakim Fund program

Job Law: Case by case, a look at decisions and their impact, quoted in the Boston Business Journal

‘Wal-Mart’ and What it Means for Future Class Actions, authored article in Massachusetts Lawyers Weekly

Advising a Massachusetts Business: Employment Agreements, author of chapter in MCLE publication

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