Position title
Compliance Specialist

Winterwood, Inc., Best Places to Work winner seven years in a row, is a growing family-owned property management company with over 40 years of experience in the industry. 

We’re looking for a motivated and driven individual to fill the position of Compliance Specialist at our Corporate office in Lexington, KY. 

The Compliance Specialist is responsible for ensuring compliance with all government housing programs (HUD, Rural Development, Tax Credit and PHA’s)  and ensures the property owner’s financial security. This position is also responsible for providing support to the field operations as it relates to maintaining program compliance regulations.  

We offer full benefits, including health insurance, paid leave time, opportunities for advance and more! 


  • High School Education required.
  • Bachelor’s Degree preferred, but not required.
  • 3+ years of Affordable Housing experience (HUD, Rural Development, Tax Credit, HOME, and PHA).
  • C3P, HCCP and COS certifications. 
  • Proficient computer skills required.
  • Ability to organize and multi-task.
  • Strong Customer Service Skills.
  • A certain degree of creativity and latitude is required.


  • Reviews and pre-approves all  move-in paperwork; annual recertifications and tenant transfers for a specific property type to ensure compliance with the program rules.
  • Trains and advises managers and supervisors of program guidelines and changes.
  • Implements changes to rents, utility allowances, income limits and policy and procedure.
  • Assist managers and supervisors on correcting compliance issues.
  • Assist in monitoring State and Federal Software for accuracy.
  • Assists managers with questions on properly inputting data into online government software programs.
  • Responsible for property status reporting to syndicators, owners and other outside government agencies.

How to Apply?

Apply online at www.winterwoodonline.com/careers

Winterwood, Inc. is proud to be an Equal Employment Opportunity

Employment Type
Job Location
Lexington, KY
Date posted
June 14, 2022
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Position: Compliance Specialist

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