Senior Compliance Specialist - Affordable Housing

Oakbrook Corporation; Madison (WI); On-site; USD 85,000 - 110,000; Full time

Job summary

Oakbrook Corporation seeks a Senior Compliance Specialist to safeguard access to housing and uphold the integrity of our communities. You will ensure programs stay accurate, fair, and aligned with federal, state, and investor requirements.

This role is ideal for experienced property management professionals who enjoy detailed analysis, audits, and meaningful impact in affordable housing compliance.

Qualifications

• Detail-oriented with a sharp focus on file reviews and documentation (HUD, LIHTC, RD, HOME, CDBG).
• Experience in affordable housing compliance and audits is preferred.
• Excellent written and verbal communication for cross-team guidance.

Responsibilities

• Review and approve resident files to ensure accurate certifications.
• Monitor property compliance with HUD, Tax Credit, and related programs.
• Support state agency and investor audits with documentation and responses.
• Interpret regulatory updates and train onsite teams on requirements.
• Maintain compliance data in OneSite and ensure accuracy.
• Assist with reporting obligations to agencies and investors.

Skills

Detail-oriented

Compliance knowledge

Strong communication

Team collaboration

Analytical thinking

Problem solving

Multitasking

Microsoft Office

Education

HCCP certification

COS certification

Tools

OneSite

Job description

At Oakbrook Corporation, compliance is more than regulations; it's about protecting access to housing and preserving the integrity of the communities we serve. As a SeniorCompliance Specialist, you'll play a critical role in ensuring our affordable housing programs remain accurate, fair, and fully aligned with federal, state, and investor requirements.

This opportunity is ideal for experienced property management professionals or compliance-minded individuals who enjoy digging into details, solving complex challenges, and making a meaningful impact. Your background in affordable housing will directly support our mission of delivering equitable, compliant housing solutions.

What You'll Do

In this role, you'll serve as a trusted compliance partner across a diverse portfolio:

• Review and approve resident files to ensure accurate, timely certifications
• Monitor property compliance with HUD, Tax Credit, RD, HOME, and other program requirements
• Prepare for and support state agency and investor audits, including responses and documentation
• Interpret evolving regulations and communicate requirements clearly to on-site teams
• Maintain compliance data within OneSite and ensure consistency and accuracy
• Assist with reporting obligations to agencies and investors
• Identify compliance risks and proactively develop solutions
• Support process improvements, forms, and internal procedures
• Provide training and guidance to property teams on compliance best practices
• Collaborate across departments to uphold Oakbrook's standards of quality and accountability

What Sets You Up for Success

You're someone who thrives in a detail-driven environment and takes pride in getting things right. You bring both technical knowledge and a thoughtful, solution-oriented approach.

• A commitment to ethical practices and doing what's right
• A sharp eye for detail and accuracy in file reviews and documentation
• Excellent communication skills: you can simplify complex requirements and build trust
• Willingness to offer assistance to coworkers and work as a team to achieve goals
• Analytical thinking and a problem-solving mindset
• Ability to manage multiple deadlines and priorities with confidence
• Proficiency in Microsoft Office and property management systems
• Strong knowledge of affordable housing programs (HUD Section 8, LIHTC, RD, HOME, CDBG, etc.)
• HCCP and/or COS certifications are a plus

Why Oakbrook?

At Oakbrook Corporation, you'll be part of a team that values integrity, collaboration, and continuous improvement. Your work will directly support the success of our communities and the residents we serve, making a meaningful difference every day.