David Guadagnoli

Tax/Employment & Benefits

David concentrates his practice in employee benefits and executive compensation. With respect to benefits, David is experienced in the design, implementation and administration of welfare and fringe benefit arrangements and qualified retirement plans (including 401(k) plans and ESOPs) for large and small employers, retirement distribution planning for individuals and the design and implementation of nonqualified deferred compensation and equity compensation arrangements for public and private employers. David has extensive practical experience with nondiscrimination testing issues, plan recordkeeping and conversion issues, IRS and DOL audits and the use of self-correction and agency-approved programs and the use of ESOPs as a succession planning tool.

David also regularly negotiates employment, severance and change in control agreements, representing both executives and employers.

With over 30 years of experience as a practitioner, and having served as a plan fiduciary and on numerous boards, David brings a pragmatic approach to his practice and regularly counsels clients in the financial services industry by advising on and negotiating investment management agreements, structuring pension plan investments to avoid ERISA where possible (using venture capital operating companies (VCOCs) and real estate operating companies (REOCs), as appropriate), and helping clients navigate fiduciary and prohibited transaction issues under ERISA when not. David has worked with clients in manufacturing, real estate, professional services, education, financial services and the not-for-profit sectors.

David regularly speaks at seminars for the New England Employee Benefits Council, Massachusetts Society of CPAs and the American Society of Pension Professionals & Actuaries. David has published innumerable client alerts on employment benefit news and developments and was instrumental in creating a COVID Resource Center on Sullivan’s website, addressing a wide variety of coronavirus related issues by writing and publishing 28 client alerts that were sent out to the firm’s clients to help them cope with the impact of the COVID-19 pandemic and understand the implications of FFCRA, retirement and welfare provisions in the CARES Act, the Paycheck Protection Program and other actions taken by state governments and the federal government.

David has shepherded the practice to recognition by U.S. News Best Lawyers, Chambers USA and The Legal 500 U.S. and has been personally consistently ranked by Chambers USA, Best Lawyers in America® and The Legal 500 U.S.

Boston University School of Law (LL.M.) Taxation Boston University School of Law (J.D., cum laude) Boston University (M.B.A., cum laude) George Washington University (B.A.