Regional Compliance Specialist (Chicago Region)

Posted Friday, August 28, 2026 at 4:00 AM At WinnCompanies, 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 WinnCompanies to explore our benefits , mission, communities, and career opportunities. About the opportunity WinnCompanies is looking for a Regional Compliance Specialist to join our team and support Low Income Housing Tax Credit, Project-Based Section 8, Project Based Voucher, and Chicago Housing Authority properties throughout Chicago, IL . The Regional Compliance Specialist is responsible for ensuring that all policies and procedures from WinnResidential and affordable housing agencies are communicate to, and implemented by site managers and senior staff within the assigned portfolio. You will also be responsible for delivering a network of training, completing compliance reviews, monitoring property-specific compliance requirements across program types, and providing direct support to the assigned portfolio to ensure properties are meeting or exceeding regulatory requirements across various agencies and organizations. Please note that the salary range for this position is $85,000.00-$90,000.00 annually. Final salary will vary based on job responsibilities and scope, geographic location, candidate’s relevant experience, and other factors. The selected candidate will adhere to the following schedule: Monday through Friday from 8:00AM to 5:00PM CST being onsite Monday through Thursday with the ability to be remote on Fridays. Responsibilities: Perform regular on site and remote audits, both scheduled and unscheduled, and assist sites in preparation of, attend, and ensure timely and complete response to agency audit findings. Manage and monitor efforts of various departments during lease up or program conversion of new and existing properties to ensure owner and investor expectations are met or exceeded. Analyze and interpret regulatory documents to ensure proper setup of property management software for new and existing assets; manage and correct as necessary through helpdesk ticketing system. Collaborate with Corporate Compliance to design, develop, and deliver trainings through either direct delivery or coordination with existing trainings provided through professional organizations. Review, revise, disseminate, and implement policies and procedures to reflect new or changing agency and/or company requirements. Collaborate with various departments to drive overall property performance through monitoring, reporting, communicating, and tracking key indicators of financial and programmatic requirements. Provide direct support and routine accessibility to internal and external customers within the assigned portfolio through attendance at regularly scheduled meetings, conference or direct calls, email, and completion of helpdesk tickets. Various other administrative duties as assigned. Requirements: High School diploma or GED. Minimum of 5 years of direct affordable housing compliance department experience. Experience working with Low Income Housing Tax Credit, Project Based Rental Assistance, Project Based Voucher, and Chicago Housing Authority. Experience with computer systems, particularly Microsoft Office Suite. A current driver's license in good standing and ability to meet the driving records standards outlined in the Company Safe Vehicular Operations Policy. Ability to manage multiple assignments and tasks. Outstanding verbal and written communication skills. Comprehend and communicate complex verbal information in English to the organization. Outstanding leadership and training skills. Demonstrated organizational, record-keeping, and interpersonal skills. Preferred Qualifications: Bachelor's degree or equivalent work experience. Certified Occupancy Specialist, C3P, CAM, CAPS, or similar designations. NAHP, SHCM, or similar designation. Experience in regional management involving multiple properties. 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 and hybrid 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