Director of Tax (Boston HQ)

WinnCompanies • Boston, MA

6d • $150,000 - $175,000 • Onsite

About The Position

WinnCompanies is seeking a Director of Tax to join its corporate team in Boston, Massachusetts. Working in partnership with another Director of Tax, this role leads tax compliance and planning for a complex portfolio of more than 600 entities, as well as approximately 150 non-filing entities. The portfolio includes partnerships, corporations, trusts, foundations, and individual returns, with a focus on the family office. The role advises on transactions affecting the company and its owners, identifies opportunities to minimize or defer taxes, and partners with internal teams and external tax advisors. It sets tax priorities and exercises independent judgment on complex issues. The position reports to the Chief Financial Officer and has no direct reports.

The stated annual pay range is $150,000–$175,000. The typical schedule is Monday through Friday, 8:00 AM to 5:00 PM.

Requirements

• Bachelor’s degree in Tax, Accounting, or a related field.
• 8–10 years of relevant experience, including public accounting tax experience.
• 3–5 years of supervisory or management experience.
• CPA or Enrolled Agent (EA) credential.
• Strong knowledge of real estate partnership and individual taxation, with a background in partnership, trust, and individual tax.
• Family office experience, including trust and individual tax experience and estate planning and estate administration experience.
• Advanced Microsoft application skills, including Excel, and proficiency with Adobe, AI tools, and web-based applications.
• Ability to analyze complex tax issues, exercise sound judgment, communicate clearly in written and spoken English, and independently manage changing priorities.
• Collaborative approach and strong service orientation, including the ability to explain complex information, provide staff training, and resolve issues promptly and respectfully.

Nice To Haves

• Master’s degree in Tax, Accounting, or a related field.
• Knowledge of trust and estate taxation.
• Experience with Internal Revenue Code Sections 754, 743(b), 704(b), 163(j), 108, and 199A.
• Experience with Microsoft Teams.

Responsibilities

• Oversee federal, state, and local tax return compliance for a portfolio of approximately 600 entities, including partnerships, corporations, trusts, condominium associations, individuals, and foundations.
• Review and sign returns as Assistant Secretary; maintain the return tracker; ensure returns and payments are filed on time; maintain state tax portal logins; and prepare workpapers for third-party preparers.
• Review returns prepared by third-party preparers; prepare and file returns and extensions; calculate and process return, extension, and quarterly estimated payments; provide tax journal entries to Accounting; and compile and distribute investor K-1s.
• Manage tax audits, respond to tax notices and investor inquiries, review engagement letters, and process bills from accounting firms.
• Research tax questions and issues and keep current with developments in tax law.
• Manage and review the Founder’s and CEO’s income and gift tax filings, provide cash-planning and estate-planning projections, work with the CFO on estate-planning initiatives, and assist with the CEO’s personal financial statements.
• Prepare income tax and cash-flow projections to support asset-management decisions.
• Complete special projects for the Chairman, CEO, CFO, and Development, Legal, Finance, Accounting, and Compliance teams, including interest tracing, partnership agreement review, cost segregation and repair regulation study coordination, W-9 preparation, capital account tracking, budgeting, 1099 analysis, special allocation tracking, and solar deal consulting.
• File personal property tax returns for management and development entities, sales and use tax returns, business privilege tax returns, 121A returns, and other miscellaneous tax forms.
• Maintain the tax credit tracker and submissions, including Forms 8609 and MA CITC; ensure credits are properly reported; and ensure Forms 8703 are filed.
• Process annual capitalization of new entities.
• Document Tax Department policies and procedures.

Benefits

• Generous paid time off, paid holidays, sick time, a floating holiday, and a day of service.
• Medical, dental, and vision coverage, plus HSA, FSA, and dependent care savings options.
• 401(k) with company match.
• Company-paid life, AD&D, and long-term disability insurance.
• Tuition reimbursement, professional development opportunities, and career growth resources.
• Wellness programs and employee assistance resources.
• Commuter benefits and employee discount programs.
• Flexible work options for eligible positions.

What This Job Offers

• Job Type: Full-time
• Career Level: Director