Vice President of Community Housing Programs

Guest House of Milwaukee•Milwaukee, WI

1d•Onsite

About The Position

Guest House of Milwaukee, a comprehensive provider of housing and supportive services for individuals experiencing homelessness, is seeking a Vice President of Community Housing Programs. This executive leadership role oversees the organization's housing portfolio, including permanent supportive housing, transitional housing, rapid rehousing, and homelessness prevention. The Vice President is responsible for strategic vision, effective service delivery, regulatory compliance, financial sustainability, and measurable impact. As part of the Executive Leadership Team, this role collaborates with other leaders to align housing strategies with agency-wide goals, improve program performance, and respond to community needs. The position also contributes to fundraising, external relations, and public representation.

Requirements

Demonstrated systems-level thinking with the ability to align housing programs with broader community housing and homelessness systems.
Strong knowledge of city, county, and federal housing funding sources and regulations, including HUD, VA, and related programs.
Deep understanding of homelessness, housing stability, mental health, and substance use challenges.
Ability to analyze and interpret complex technical and non-technical documents, including contracts, policies, audits, proposals, and financial reports.
Proven ability to manage multiple projects and priorities in a dynamic environment.
Excellent verbal and written communication skills.
Valid driver’s license, vehicle insurance, and reliable transportation in compliance with agency requirements.
Bachelor’s degree in social work, psychology, or related field required.
Minimum of five (5) years of senior-level program management and leadership experience.
Experience with program development, implementation, and evaluation, including use of logic models, dashboards, or similar performance tools.
Experience in a Microsoft 365 environment.

Nice To Haves

Master’s degree strongly preferred

Responsibilities

Provide executive oversight for all community housing programs, including but not limited to Homelinc, My Home, Housing First, VA TIP, Rapid Rehousing, Landlord and Lease Management, Homeless Prevention, and Community Case Management.
Directly supervise housing program directors and ensure strong leadership, accountability, and performance across all programs.
Ensure a high-quality, compliant, and financially sustainable service delivery system across the housing continuum.
Develop, implement, and regularly review systems, policies, and procedures to ensure effective coordination and communication across programs and departments.
Design and maintain a comprehensive program evaluation framework, incorporating process measures, outcomes, and client satisfaction data, and lead continuous quality improvement efforts.
Maintain strong working knowledge of housing-related grants, contracts, and funding requirements, including fiscal oversight, audits, and corrective action processes.
Partner with and serve as backup to the Director of Government Grants and Quality Assurance on evaluation, reporting, and compliance for housing-related funding.
Lead a standardized annual planning process across all housing programs, with clear goals, budgets, and performance indicators; provide summaries to executive leadership and, as appropriate, the Board.
Identify and research funding opportunities, program models, and community resources to support program growth and innovation aligned with the organization’s mission.
Support program development, budget planning, and sustainability strategies.
Build and maintain strong collaborative relationships with funders, government entities, landlords, community partners, and other stakeholders.
Work closely with the CEO to advance the organization’s mission, vision, and strategic priorities.
Stay informed on federal, state, and local legislation and policy changes impacting housing and homelessness services.
Represent Guest House in external forums, fundraising efforts, and public relations activities as needed.
Develop and oversee policies and procedures that ensure the health, safety, and well-being of clients and staff.
Respond promptly to emergencies and lead or support crisis intervention efforts as required.
Perform other duties and special projects assigned by the CEO.