Senior Support Specialist (Boston HQ) Job at WinnCompanies in Boston

Overview

WinnCompanies is looking for a motivated Senior Support Specialist to join our Corporate team based in Boston, MA. The salary range is $73,000.00/yr - $85,000.00/yr. In this role, you will provide hands-on operational support to assigned communities, addressing lease-ups, compliance, staffing gaps, and other property-level challenges. The ideal candidate will also support and travel (up to 95%) to various sites assisting with day-to-day operations, training, and implementation of company standards.

The salary range for this opportunity is $73,000-$85,000 annually dependent on experience. The selected candidate will adhere to the following schedule: Monday through Friday from 9:00 AM to 5:00 PM.

Responsibilities

• Provide on-site operational support to communities facing staffing shortages or operational challenges, including leasing, rent collection, HUD/LIHTC compliance, marketing and physical inspections.
• Carry out specialized compliance projects at properties requiring intensive support (e.g., catching up on large volumes of past-due resident recertifications to restore compliance).
• Conduct full recertification cycles in response to programmatic changes (e.g., funding shifts, regulatory updates).
• Travel extensively to perform documentation reviews providing hands-on assistance to meet deadlines and avoid regulatory penalties.
• Play a key role in lease-up efforts at new or transitioning communities.
• Provide on-site leasing support to help meet occupancy goals and timelines.
• Ensure compliance with HUD/LIHTC requirements during lease-up phases, including documentation and recertifications.
• Work closely with site teams and support departments to facilitate a smooth lease-up process.
• Support WinnSTART / STOP processes, including property setup tasks, vendor coordination and onboarding support to ensure smooth transitions.
• Participate in due diligence activities such as lease file audits and physical inspections.
• Contribute to documentation and analysis of findings to support operational readiness.
• Facilitate training efforts for on-site staff, focusing on operational procedures, compliance standards and customer service excellence.

Requirements

• High school diploma or GED equivalent.
• 1-3 years of relevant work experience.
• 1-3 years of supervisory / management experience.
• 2 years of experience in affordable multi-family property management.
• Strong understanding of HUD / LIHTC programs.
• Proven marketing and leasing experience at market rate multifamily communities is a plus.
• A current driver's license in good standing and ability to meet the driving records standards outlined in the Company Safe Vehicular Operations Policy.
• Advanced skills with Microsoft applications which may include Outlook, Word, Excel, PowerPoint or Access and other web based applications.
• Ability to produce complex documents, maintain databases and perform analysis.
• Excellent customer service skills.
• Outstanding verbal and written communication skills.
• Ability to manage multiple assignments and tasks.
• Ability to collaborate with various stakeholders across the organization.

Preferred Qualifications

• Bachelor's degree.
• Previous experience with property management software such as Yardi or RealPage OneSite.

Our Benefits

• Generous time off policies (including 11 paid holidays; 12 for MA employees) and accrued paid time off.
• 401(k) plan options with a company match
• Medical, Dental, & Vision plan options
• Flexible Spending Account, Health Savings Account options with employer contributions
• Long Term Disability and voluntary Short Term Disability; Basic Term Life Insurance and AD&D; optional supplemental life insurance
• Health Expense Reimbursement program and related benefits
• Tuition Reimbursement and ongoing training opportunities
• Wellbeing program, Employee Assistance Program, and commuter/parking reimbursement
• Employee Corporate Discount Programs
• Flexible and/or Hybrid schedules available for certain roles
• Employee Relief Program for unexpected hardships

About WinnCompanies

WinnCompanies is a mission-driven, national business focused on building and operating top quality affordable housing communities for individuals and families of all incomes, including members of the U.S. Armed Forces and their families. Our 4,300+ team members work across 27 states, Washington, D.C., and Puerto Rico to create thriving living communities. If you are a California resident, please see our Notice of Collection here. Salary will vary based on job responsibilities, geographic location, candidate experience, and other factors. Current Winn employees should apply through our internal link.