Senior Support Specialist (Boston HQ)

At Winn. Companies, our work starts with people — the residents who call our communities home, the neighborhoods we help strengthen, and the 4,600+ team members across 30 states, Washington, D.C., and Puerto Rico who make it all possible. As an award-winning owner, developer, and manager of high-impact, mixed-income apartment communities, we are proud to be one of the nation’s leading managers of multifamily housing and one of the largest operators of affordable housing communities.

We bring together people who care about quality housing, meaningful service, and making a difference every day. Through our innovative resident services platform and commitment to exceptional communities, we offer career opportunities for individuals who want their work to create lasting impact. Interested in learning more?

Visit Winn. Companies to explore our benefits , mission, communities, and career opportunities. About the Opportunity Winn. Companies 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 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. 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 Real. Page One. Site.

Benefits

& Perks Eligible full-time U.S. employees enjoy a competitive benefits package, including: Generous paid time off, paid holidays, sick time, a floating holiday, and a day of service Medical, dental, and vision coverage, plus HSA, FSA, and dependent care savings options 401(k) with company match and company-paid life, AD&D, and long-term disability insurance Tuition reimbursement, professional development opportunities, and career growth resources Wellness programs, employee assistance resources, commuter benefits , and employee discount programs Flexible work options for eligible positions Learn more about our benefits at https://www.

winnbenefits.com . If you are a California Resident, please see our Notice of Collection here . It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Salary will vary based on job responsibilities and scope, geographic location, candidate’s relevant experience, and other factors. Internal candidates, please apply here: Internal Careers Hub