Director of Tax

At WinnCompanies, 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 WinnCompanies to explore our benefits, mission, communities, and career opportunities.

About the Opportunity 

WinnCompanies is looking for a detailed and motivated Director of Tax to join our corporate 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. You will be based out of our Boston, MA Headquarters located at One Washington Mall, Boston, MA 02108 (Government Center) on Mondays-Thursdays with the option to work remotely on Fridays.

• Co-lead federal, state and local tax compliance across 30 states for partnerships, including more than 125 audited rental real estate operating partnerships and related entities, C- and S-corporations, trusts, condominium associations, individuals and foundations.
• Oversee return preparation, review and signing as Assistant Secretary; extensions; estimated payments; supporting workpapers; tax journal entries; and investor K-1 delivery. Maintain filing trackers and state tax portal access to ensure timely returns and payments.
• Manage external tax preparers, engagement letters and invoices; oversee tax audits; and resolve tax notices and investor inquiries.
• Research tax issues, monitor legislative developments and advise on transactions. Prepare income tax and cash flow projections to support asset management and tax planning decisions.
• Manage the Founder’s and CEO’s income and gift tax filings and related audits. Provide cash and estate planning projections, partner with the CFO on estate planning initiatives, and assist with the CEO’s personal financial statements.
• Lead the tax support of the family office, including trust and individual income and gift tax compliance, estate planning, and estate and trust administration.
• Support the Chairman, CEO, CFO and Development, Legal, Finance, Accounting and Compliance teams on partnership agreements, interest tracing, cost segregation and repair regulation studies, capital accounts, special allocations, solar transactions, W-9s, 1099 analysis and budgeting.
• Oversee personal property, sales and use, business privilege, 121A and other miscellaneous tax filings; maintain tax credit tracking and submissions, including Forms 8609 and Massachusetts CITC; ensure proper credit reporting and Form 8703 filings; and process annual capitalization of new entities.
• Document tax policies and procedures, recommend process improvements, and support departmental budget planning and monitoring.

• Bachelor’s degree in Tax or Accounting, Master's degree preferred.
• 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.

• 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