Vice President, Compliance; Boston, MA

Posted Friday, February 13, 2026 at 5:00 AM

Winn Companies is searching for a Vice President, Compliance to join our team and manage a portfolio of assets located throughout the Boston, MA region.

In this role, you will serve as the right hand to the Senior Vice President of Compliance and based in Boston, providing direct oversight and operational leadership for compliance functions across the organization’s affordable housing portfolio. The ideal candidate will be responsible for developing and mentoring team members, ensuring consistent compliance practices, and maintaining alignment with organizational objectives and client needs.

The VP, along with the SVP, will implement innovative solutions, drive operational excellence, and support the company’s compliance vision. The VP also leverages technology and data analytics to automate reporting and enhance efficiency, ensuring compliance excellence in a dynamic regulatory environment.

The salary range for this position is $-$ per year dependent on experience with an annual bonus potential up to 20%. The selected candidate will adhere to the following hybrid schedule:
Monday through Friday from 8:00 AM to 5:00 PM (onsite 4 days per week).

• Provide leadership development and mentorship to compliance team members, fostering a culture of continuous growth and high performance.
• Identify and cultivate emerging talent, ensuring a strong pipeline of future leaders.
• Oversee recruitment and onboarding of new staff, equipping them for success in affordable housing compliance roles.
• Oversee compliance metrics for the Winn managed affordable portfolio, implementing digital tools and platforms to automate data collection and analysis.
• Ensure timely and accurate compliance with federal, state, and local reporting requirements.
• Utilize centralized systems to monitor performance, generate reports, and maintain comprehensive records for transparency and accountability.
• Ensure consistent compliance practices and standards are implemented and maintained across all regions and program types.
• Partner with the Senior Vice President, who leads company-wide strategic compliance business initiatives.
• Support the SVP in executing cross-functional projects, driving innovation, and advancing operational excellence throughout the compliance function.
• Deliver timely, accurate, and actionable insights to senior leadership, clients, and regulatory agencies.
• Communicate clearly and confidently, promoting portfolio-wide alignment and effectiveness.
• Perform other responsibilities as assigned.

• High school diploma or GED equivalent.
• 8-10 years of affordable housing compliance experience.
• 5-8 years of supervisory / management experience.
• Advanced skills with web-based applications and computer systems such as Microsoft Office Suite.
• A current driver's license in good standing and ability to meet the driving records standards outlined in the Company Safe Vehicular Operations Policy.
• Ability to travel up to 25% of the time when required.
• Ability to align compliance operations with organizational goals and anticipate regulatory changes.
• Proven experience in developing, mentoring and managing high-performing teams.
• Strong ability to leverage data analytics and digital tools to drive decision-making and process improvements.
• Excellent verbal and written communication skills, with the ability to present complex information clearly to diverse audiences.

• Deep knowledge of affordable housing compliance requirements across multiple regulatory programs (such as LIHTC, HUD, HOME, and others) and states, with the ability to interpret, implement, and ensure adherence to complex and evolving regulations.

• Generous time off policies (including 11 paid holidays (12 for MA employees);
  Generous Accrued Time Off increasing with years of service; Generous paid sick time; Annual day of service; Floating Holiday)
• 401(k) plan options with a company match
• Various Comprehensive Medical, Dental, & Vision plan options
• Flexible Spending Account, Dependent Care Flexible Spending Account, Health Savings Account options with HSA annual employer contribution
• Long Term Disability…