Senior Support Specialist (boston HQ)

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.