Senior Support Specialist (Boston HQ)

WinnCompanies; Baltimore (MD); On-site; USD 73,000 - 80,000; Full time

Job summary

WinnCompanies is seeking a Senior Support Specialist for its corporate team based in Washington, D.C. You will provide hands-on operational support to assigned communities, focusing on lease-ups, compliance, staffing gaps, and other challenges.

The role requires up to 100% travel to sites, training staff, and implementing company standards. The position involves extensive site visits, documentation reviews, and collaboration with multiple teams to ensure HUD/LIHTC compliance and occupancy goals

Qualifications

• High school diploma or GED required; 1–3 years of relevant experience.
• Experience with HUD/LIHTC programs and leasing operations strongly preferred.
• Strong customer service and communication skills; ability to multitask.

Responsibilities

• Provide on-site operational support to communities facing staffing or compliance challenges.
• Support lease-up activities, HUD/LIHTC compliance, marketing, and inspections.
• Travel extensively to assist sites, train staff, and ensure program adherence.
• Perform lease file audits, due diligence, and documentation reviews.
• Collaborate with site teams and support departments to meet occupancy goals.

Skills

Customer service

Verbal and written communication

Time management / multitasking

Collaborative work

HUD/LIHTC program knowledge

Education

High school diploma or GED

Bachelor's degree (preferred)

Tools

Microsoft Office Suite

Job description

About the Opportunity

WinnCompanies is looking for a motivated Senior Support Specialist to join our corporate team based out of Washington, D.C

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 100%) to various sites assisting with day‑to‑day operations, training, and implementation of company standards.

The salary range for this opportunity is $73,000.00-$80,000.00 annually dependent on experience. Please note the selected candidate will adhere to the following schedule: Monday through Friday from 9:00AM to 5:00PM which is dependent on certain on‑site hours.

Responsibilities:

• Provide on‑site operational supportto communities facing staffing shortages or operational challenges, including leasing, rent collection, HUD/LIHTC compliance, marketing and physical inspections.
• Carry out specialized compliance projectsat 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 effortsat 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 effortsfor 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.
• This role has a 100% travel requirement.
• Minimum of 2 years of hands‑on experience working with HUD programs.
• Strong understanding of Project‑Based Section 8 and/or 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.