Senior Support Specialist (Boston HQ)

WinnCompanies•Washington, DC

About The Position

WinnCompanies is seeking a Senior Support Specialist to join its corporate team. The role provides hands-on operational support to assigned communities, addressing lease-ups, compliance, staffing gaps, and other property-level challenges. The position involves travel to various sites—up to 100%—to support day-to-day operations, train staff, and implement company standards. The listed salary range is $73,000 to $80,000 annually, dependent on experience. The schedule is Monday through Friday, 9:00 a.m. to 5:00 p.m., with certain on-site hours.

Requirements

High school diploma or GED equivalent.
1–3 years of relevant work experience.
1–3 years of supervisory or management experience.
2 years of experience in affordable multifamily property management.
At least 2 years of hands-on experience working with HUD programs.
Strong understanding of Project-Based Section 8 and/or LIHTC programs.
Current driver's license in good standing and ability to meet the driving record standards in the Company's Safe Vehicular Operations Policy.
Advanced skills with Microsoft applications, potentially including 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 stakeholders across the organization.
Ability to travel up to 100%.

Nice To Haves

Proven marketing and leasing experience at market-rate multifamily communities.
Bachelor's degree.
Previous experience with property management software such as Yardi or RealPage OneSite.

Responsibilities

Provide on-site operational support to communities experiencing 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, such as catching up on past-due resident recertifications.
Conduct full recertification cycles in response to programmatic changes, including funding shifts and regulatory updates.
Travel extensively to conduct documentation reviews and provide hands-on assistance to meet deadlines and avoid regulatory penalties.
Support lease-up efforts at new or transitioning communities, including on-site leasing assistance to meet occupancy goals and timelines.
Ensure HUD/LIHTC compliance during lease-up phases, including documentation and recertifications.
Work with site teams and support departments to facilitate smooth lease-ups.
Support WinnSTART/STOP processes, including property setup, vendor coordination, and onboarding support.
Participate in due diligence activities, including lease file audits and physical inspections.
Document and analyze due diligence findings to support operational readiness.
Facilitate training for on-site staff on operational procedures, compliance standards, and customer service.