Director of Drop-In Services

Summary of Position: The Director of Drop-In Services provides leadership and oversight for CFTH’s Drop-In Centers at Dewey and Hilda’s Place. This role ensures high-quality daily operations, a welcoming environment for participants, and strong coordination across teams. The Director oversees process-level staff across Drop-In operations, case management, outreach, and coordinated entry; oversees volunteers; maintains program compliance; and supports a consistent, trauma-informed approach to services. The Director ensures all service areas operate efficiently, safely, and in alignment with agency policies, core values, and funder requirements. The role will also support the development and future implementation of expanded service models, including the potential integration of overnight shelter operations as the program grows.

Specific Duties:

Leadership & Team Support

• Lead Drop-In-related programs in alignment with CFTH’s core values.
• Supervise and support managers and staff across Drop-In operations, case management, outreach, and coordinated entry.
• Provide coaching, clarity, and consistent expectations for staff across service areas.
• Promote a collaborative and accountable team environment.
• Model trauma-informed, participant-centered practices and professional boundaries.
• Provide direct case management or participant support when needed.

Operations & Safety

• Oversee daily operations across both Drop-In Centers, including intake, triage, resource distribution, hygiene access, case management workflows, and participant flow.
• Support coordination between Drop-In, case management, outreach, and coordinated entry teams.
• Develop, maintain, and update SOPs and workflows to support efficient operations.
• Maintain a consistent on-site presence to support staff and monitor services.
• Ensure compliance with safety practices, incident reporting expectations, and operational policies.
• Collaborate with Operations, Facilities, and the Safety Committee regarding environment, safety concerns, and building needs.

Data, Reporting & Compliance

• Lead expectations for accurate, timely data entry, including HMIS or other funder-required systems.
• Ensure reporting and documentation meet CoC, HUD, DFSS, coordinated entry, and other contract requirements.
• Conduct routine file reviews, data checks, and quality assurance processes across all service areas.
• Partner with Development and Finance on grant reporting, audits, and compliance documentation.

Volunteer Engagement & Development Collaboration

• Oversee volunteer involvement within Drop-In Services in partnership with the Development team.
• Ensure volunteers receive clear orientation, expectations, and support.
• Maintain open communication with Development to promote a positive volunteer experience and alignment across teams.

Cross-Department Coordination

• Strengthen partnerships with Outreach, Housing, Case Management, Health, and Operations teams.
• Support clear internal referral pathways and collaborative problem-solving.
• Participate in agency leadership meetings and cross-team initiatives.

External Partnerships

• Build and maintain appropriate connections with community partners and local service providers.
• Represent Drop-In Services, Case Management, Outreach, and Coordinated Entry in collaborative meetings as needed.

Safety, Risk Management & Incident Response

• Ensure all staff understand and follow safety expectations and participant engagement guidelines.
• Oversee incident reporting and follow-up; communicate with leadership as needed.
• Support a safe environment for staff, volunteers, and participants.
• Identify safety trends and participate in improvement planning with the Safety Committee.

Future Service Expansion

• Participate in planning and development of expanded service models, including the potential integration of overnight shelter operations or extended service hours.
• Support implementation of new program components as CFTH’s service portfolio grows.

Additional Responsibilities

• Support operations during high-volume periods, weather emergencies, or urgent needs.
• Occasional evening or weekend hours may be required
• Adheres to the Code of Conduct and Core Values of Connections for the Homeless
• Other duties as assigned.

The following qualifications are requirements for the position:

• Minimum 5 years of leadership experience in human services, homelessness services, behavioral health, or related fields
• Experience supervising managers or process leads across multiple program functions or service areas.
• Strong operations and systems-building skills, including SOP development and accountability management.
• Knowledge of trauma-informed care and harm reduction principles.
• Ability to manage data integrity expectations, including HMIS or comparable systems.
• Strong communication, problem-solving, and relationship-building skills.
• Ability to remain steady and professional in dynamic environments.
• Commitment to CFTH’s mission and core values.

The following qualifications are highly desirable:

• Experience working with HUD, CoC, DFSS, or coordinated entry frameworks
• Experience in drop-in centers, shelters, outreach, or case management settings.
• Experience working with volunteers or volunteer-supported programs.
• Familiarity with local homelessness systems and community partnerships.

Working Conditions

• Primarily on-site across CFTH’s Drop-In Centers at Dewey and Hilda’s Place.
• Dynamic service environment with diverse participant needs.
• Occasional nonstandard hours or travel within the community may be required.

Other Requirements:

• Must submit to a criminal background check and submit to or provide evidence of a recent test for tuberculosis.

For nearly 40 years, Connections for the Homeless has served and catalyzed our community to end homelessness, one person at a time. Each year we provide eviction prevention, shelter, and housing services to 4,000 people from across north suburban Cook County. Beyond providing direct services we also operate a robust advocacy and community organizing program to address the root causes of homelessness. The COVID pandemic accelerated our growth in the depth and breadth of services we offer and the organizational infrastructure to sustain this highly impactful organization. Connections is a radically reshaped organization deeply committed to demonstrating our core values in all relationships with participants, colleagues, donors, partners, and volunteers.

Join our dedicated team at Connections for the Homeless, where we blend a commitment to making a difference with a competitive rewards package. Our full-time employees enjoy a range of benefits, consciously crafted through an equitable lens, to support their well-being and professional growth.

At Connections for the Homeless, we recognize that supporting our employees is essential in achieving our mission. We are ready to invest in you as you make a difference in our community. We can't wait for you to join us!