Outreach Supervisor

Lee County is seeking a compassionate and dependable Housing Outreach Supervisor to lead street outreach services for individuals and families experiencing homelessness.

In this role, you will guide outreach staff, work directly in the community, and help connect people to housing, healthcare, and support services. Your work will play an important role in improving lives, supporting veterans and vulnerable populations, and strengthening Lee County’s homeless response system.

This position is ideal for someone who values meaningful public service, enjoys leadership, and is committed to helping people in crisis.

• Lead and supervise a team of homeless outreach staff
• Coordinate street outreach services across Lee County
• Ensure outreach work follows HUD rules, grant requirements, and county policies
• Spend regular time in the field supporting staff and engaging with clients
• Assist individuals living in encampments, on the streets, and in unsafe locations
• Organize Housing Outreach & Treatment (HOT) events and severe weather outreach
• Track encampments and help respond to high-need or crisis situations
• Enter and maintain client records in the Homeless Management Information System (HMIS)
• Attend and lead weekly By-Name List (BNL) meetings to support housing placement
• Assign work, conduct evaluations, and address performance concerns
• Provide staff onboarding, training, and ongoing coaching
• Lead team meetings, individual supervision, and case reviews
• Work closely with shelters, housing providers, outreach teams, and community partners
• Respond to client complaints and appeals
• Travel throughout the county as needed
• Perform other related duties as assigned

• Any combination of education and experience equivalent to a bachelor’s degree in human services or a closely related field (such as social work, psychology, sociology, counseling, public administration, or similar fields)
• One (1) year of experience in human services or a related area
• Prior supervisory or lead experience
• Valid driver’s license with an acceptable driving record
• Ability to work independently and make sound decisions in the field
• Strong communication and teamwork skills

• Experience working with people experiencing homelessness or housing instability
• Knowledge of trauma-informed care and harm-reduction practices
• Familiarity with the Homeless Continuum of Care system
• Strong computer skills, including Microsoft Word, Excel, and Outlook
• Compassionate, patient, and respectful approach

• Work takes place both indoors and outdoors
• Regular outdoor work in all types of weather
• Work Schedule: Monday – Friday, 8:00 AM – 5:00 PM.
• Occasional weekend work may be required

This is a hands-on role where your work makes a real difference. You will help individuals and families move toward safety, stability, and housing while supporting Lee County’s mission to serve its most vulnerable residents. You’ll gain valuable leadership experience and work alongside dedicated professionals committed to public service.

The Lee County Department of Human & Veteran Services supports individuals, families, and veterans through housing assistance, outreach, and coordinated care. The outreach team works across the community to connect people with resources and promote long-term stability.

Lee County is located in beautiful Southwest Florida and is home to over 700,000 residents. We are dedicated to serving our community with high-quality services and a focus on sustainability and innovation. Join us in making Lee County a great place to live, work, and visit. Find out more about Lee County at Lee County Government.