Senior Support Specialist (Boston HQ)

WinnCompanies is looking for a motivated Senior Support Specialist to join our Corporate team based in Boston, MA.
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. Please note the selected candidate will adhere to the following schedule: Monday through Friday from 9:00AM to 5:00PM.

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 (ex. 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, but not limited to: 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's such as Yardi or RealPage OneSite.

Our Benefits:Regular full-time US employees are eligible to participate in the following benefits: - 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 and voluntary Short Term Disability; Basic Term Life Insurance and AD&D; optional supplemental life insurance - Health Expense Reimbursement program (including gym memberships, equipment, and subscriptions) - Tuition Reimbursement program and continuous training and development opportunities - Wellbeing program (group challenges, seminars, opportunities to earn points to reduce medical premiums), Employee Assistance Program, & Commuter and Parking Reimbursement options - Employee Corporate Discount Programs (Verizon Wireless, Home Depot Pro, Staples, and more!) - Flexible and/or Hybrid schedules are available for certain roles - Employee Relief Program supporting employees with unexpected hardships that place undue financial s