Senior Support Specialist (Boston HQ)

WinnCompanies • Washington, DC

5d • $73,000 - $80,000

About The Position

WinnCompanies is seeking a Senior Support Specialist to provide hands-on operational support to assigned multifamily communities, including support for lease-ups, compliance needs, staffing shortages, and other property-level challenges. The role involves extensive travel to sites to assist with day-to-day operations, provide training, and implement company standards.

The position is based with the corporate team and follows a Monday-through-Friday schedule from 9:00 a.m. to 5:00 p.m., with hours dependent on certain on-site requirements. The salary range is $73,000–$80,000 annually, depending on experience. The role requires travel up to 100%.

Requirements

• High school diploma or GED equivalent.
• 1–3 years of relevant work experience.
• 1–3 years of supervisory or management experience.
• At least 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 company's Safe Vehicular Operations Policy driving-record standards.
• 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 with 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 completing overdue resident recertifications.
• Conduct full recertification cycles in response to funding shifts, regulatory updates, or other programmatic changes.
• Travel extensively to review documentation and provide hands-on assistance to meet deadlines and avoid regulatory penalties.
• Support lease-up efforts at new or transitioning communities.
• Provide on-site leasing support to help meet occupancy goals and timelines.
• Ensure HUD/LIHTC compliance during lease-up, including required documentation and recertifications.
• Work with site teams and support departments to facilitate smooth lease-up processes.
• Support WinnSTART/STOP processes, including property setup, vendor coordination, and onboarding.
• Participate in due diligence activities, including lease file audits and physical inspections.
• Document and analyze findings to support operational readiness.
• Train on-site staff on operational procedures, compliance standards, and customer service.

Benefits

• 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.
• Company-paid life, AD&D, and long-term disability insurance.
• Tuition reimbursement, professional development opportunities, and career growth resources.
• Wellness programs and employee assistance resources.
• Commuter benefits and employee discount programs.
• Flexible work options for eligible positions.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: High school or GED