Macaulay's documented life is rooted in the Boston area, where he studied at Boston College and Suffolk University and later built his legal career.
Boston, the capital of Massachusetts, was the setting for both his education and the professional institutions in which he worked.
Macaulay received a Bachelor of Arts from Boston College, graduating cum laude in 1972. Boston College was founded by the Society of Jesus in 1863 and opened in Boston's South End in 1864 with three teachers and twenty-two students. Its Jesuit founders aimed to give the sons of immigrants a Catholic moral and religious framework alongside a rigorous education. The college later moved to Chestnut Hill on the western edge of Boston, where its main campus is located today.
He then studied at Suffolk University, receiving a Juris Doctor in 1976, graduating cum laude and ranking fourth in his class. Suffolk was founded in 1906 by Gleason Archer as an evening law school for workers and immigrants. Its law school was established to offer legal education to people who had traditionally been excluded from it because of socio-economic or racial discrimination.
Macaulay was admitted to the Massachusetts bar in 1977 and later became admitted to practice in Pennsylvania.
Macaulay's career began in corporate counsel work. He was associate counsel with John Hancock Mutual Life Insurance Company, a Boston-based life insurer founded in 1862. Insurance companies at the time relied on in-house lawyers to manage contracts, regulatory compliance, and employee benefit arrangements.
He then spent twelve years as a principal in the Benefits Consulting Group of Ropes & Gray, a Boston law firm founded in 1865. Benefits consulting combined legal and actuarial-style advice on retirement plans, health coverage, and other welfare programs for employers.
Macaulay later joined Parker, Brown, Macaulay & Sheerin, P.C., a firm that Steve Parker and Carol Brown established in 2001 to specialize in employee benefits and executive compensation. The firm concentrates exclusively on employee benefits law, advising employers on plans governed by the federal Employee Retirement Income Security Act of 1974 (ERISA) and on related rules such as COBRA and HIPAA. Its offices are in Boston and Newport, Rhode Island.
He has helped employers implement benefit plans and resolve disputes under ERISA, COBRA, and HIPAA, and has represented health maintenance organizations, insurers, third-party administrators, and other service providers to welfare benefit plans. He has written and spoken on employee benefits, including presentations at meetings of the New England Employee Benefits Council and the Tax Section of the American Bar Association, the national professional association of lawyers founded in 1878.
He also worked as a partner of South Eggeuno.
