Director of Tax (Boston HQ)

At Winn. Companies, our work starts with people — the residents who call our communities home, the neighborhoods we help strengthen, and the 4,600+ team members across 30 states, Washington, D.C., and Puerto Rico who make it all possible. As an award-winning owner, developer, and manager of high-impact, mixed-income apartment communities, we are proud to be one of the nation’s leading managers of multifamily housing and one of the largest operators of affordable housing communities.

We bring together people who care about quality housing, meaningful service, and making a difference every day. Through our innovative resident services platform and commitment to exceptional communities, we offer career opportunities for individuals who want their work to create lasting impact. Interested in learning more?

Visit Winn. Companies to explore our benefits , mission, communities, and career opportunities. About the Opportunity Winn. Companies is looking for a detailed and motivated Director of Tax to join our cor por a t e team located in Boston, MA. The Director of Tax works in partnership with another Director of Tax to lead tax compliance and planning for a complex portfolio of more than 600 entities, plus approximately 150 non-filing entities, with responsibilities spanning partnerships, corporations, trusts, foundations and individual returns.

This role has a focus on the family office, and we are seeking a candidate with family office experience, including trust and individual tax experience, estate planning and administration experience. Reporting to the Chief Financial Officer, this 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.

The position sets tax priorities, exercises independent judgment on complex issues and has no direct reports. Please note that the pay range for this position is $150,000 - $175,000 annually. Final salary will vary based on job responsibilities and scope, geographic location, candidate’s relevant experience, and other factors.

Additionally, the selected candidate will typically work: Monday through Friday, from 8:00 AM to 5:00 PM.

Responsibilities

Oversees the federal and (30) state tax and various local return compliance process for approximately 600 partnerships (including over 125 audited rental real estate operating partnerships with related upper tier entities, management companies, development companies & holding companies), 20 C-corporations, 15 S-corporations, 40 trusts (grantor & complex), 10 condo associations 2 individuals and 4 foundations.

Duties include reviewing and signing returns (as Assistant Secretary), maintaining the tracker, ensuring all returns and payments are timely filed, maintaining state tax portal logons, creating workpapers for third party preparers, reviewing tax returns prepared by third party preparers, preparing/filing returns and extensions, calculating & processing tax return/extension/quarterly estimated payments, providing tax journal entries to accounting department, compiling & providing K1s to investors.

Managing tax audits & responding to tax notices and investor queries. Reviewing engagement letters and processing bills from accounting firms. Researches tax related questions and issues and keeps abreast of developments in tax law. Manages/reviews Founder’s and CEO’s income tax and gift tax return filing and provides projections for cash planning and estate planning.

Works with CFO on estate planning initiatives. Assists with preparation of CEO personal financial statements. Manages tax return audits. Prepares income tax and cash flow projections to assist in asset management decisions. Completes special projects for the Chairman, CEO, CFO and the following teams: Development, Legal, Finance, Accounting and Compliance.

(e.g. interest tracing tracking, partnership agreement review, cost seg/repair reg study coordination, W9 preparation, capital account tracking, budgeting, 1099 analysis, special allocation tracking, solar deal consulting etc.) Files personal property tax returns for management & development entities, sales & use tax returns, business privilege tax returns, 121A returns & other miscellaneous tax forms.

Maintains tax credit tracker and submissions including Forms 8609 and MA CITC and ensures credits are properly reported and ensures Forms 8703 are filed. Processes annual capitalization of new entities. Documents policies and procedures for the Tax Department.

Requirements

Bachelor’s degree in Tax, Accounting or 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, apply sound judgment, communicate clearly in writing and verbally in English, and manage changing priorities independently.

Collaborative approach and strong service orientation, with the ability to explain complex information, provide staff training and resolve issues promptly and respectfully.

Preferred Qualifications

Master’s degree in Tax, Accounting or 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.

Benefits

& Perks Eligible full-time U.S. employees enjoy a competitive benefits package, including: 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 and company-paid life, AD&D, and long-term disability insurance Tuition reimbursement, professional development opportunities, and career growth resources Wellness programs, employee assistance resources, commuter benefits , and employee discount programs Flexible work options for eligible positions Learn more about our benefits at https://www.

winnbenefits.com . If you are a California Resident, please see our Notice of Collection here . It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Salary will vary based on job responsibilities and scope, geographic location, candidate’s relevant experience, and other factors. Internal candidates, please apply here: Internal Careers Hub