Overview

Shaylor is a nationally recognized authority in qualified retirement plans and specifically employee stock ownership plans (ESOPs).   With more than 20 years of experience advising companies, trustees, and fiduciaries on the design, implementation, and ongoing administration of employee stock ownership plans, he has represented clients in over 100 ESOP transactions, including initial formations, leveraged and non-leveraged transactions, refinancings, and post-transaction restructurings.

Shaylor regularly counsels clients throughout the full ESOP lifecycle—from structuring, through transaction execution and closing, to ongoing ERISA compliance, plan administration, and fiduciary matters. His practice spans both transactional and regulatory aspects of ESOPs, allowing him to provide integrated, practical advice tailored to each client’s objectives.

Clients value Shaylor’s ability to distill highly complex ERISA, tax, and corporate law issues into clear, understandable guidance. He is known for helping business owners, executives, and trustees understand not only the technical requirements of ESOPs, but also their practical implications and long-term strategic impact.

Shaylor is deeply committed to employee ownership and the role ESOPs play in promoting sustainable growth, succession planning, and employee engagement. He approaches each engagement with a focus on clarity, collaboration, and delivering solutions that support both compliance and long-term success.

Featured endorsements

Experience

Credentials

Education

Case Western Reserve University School of Law, 2006, J.D.
Trinity College, 2002, B.S.
  • Mechanical Engineering and Applied Mathematics

Clerkships and Bar Admissions

Ohio
U.S. District Court for the Northern District of Ohio

More

  • Member, American Bar Association
  • Member, Cleveland Metropolitan Bar Association
  • Employee Stock Ownership Plan (ESOP) Association
  • Board Member, Advantage Cleveland
  • Former Board Member, Leukemia & Lymphoma Society, Northern Ohio Chapter
  • Member, Worldwide Employee Benefits Network, Cleveland Chapter
  • Leadership Circle, United Way of Greater Cleveland
  • Cabinet Member, GeneratioNext (2006-2009)
  • Listed, The Best Lawyers in America®,  Employee Benefits (ERISA) Law, 2020-2026
  • Listed, Chambers USA, Employee Benefits & Compensation, 2018-2020, 2022
  • Listed, Super Lawyers – Rising Stars 2011, 2013, 2016