Enrollment and Outreach Supervisor (SSVF)

Internal Opportunities Fairfield, CA


Description

Compensation: $70k+ DOE
Benefits:   
  • Free Health, Dental, & Vision (50% of coverage paid for dependents)
  • Affordable Chiropractic and Acupuncture benefits
  • 19 Paid Holidays- (22 paid holidays in 2024!)
  • 15 Vacation Days, with annual increase
  • Retirement Plan with a match
  • Paid Training
  • 10-year anniversary sabbatical
  • Flexible Spending Accounts
  • Professional Development Allowance
  • Paid Parental Leave benefit
  • Discounted Pet Insurance
  • and many more!

Company Overview

For more than 50 years, Insight Housing has provided a comprehensive range of housing, food, and support services to help those in need move from homelessness into a safe and affordable home of their own. We serve in seven counties in the bay area - Alameda, San Francisco, Contra Costa, Solano, Sacramento, San Joaquin, and Amador County. We are proud of our team members who are very dedicated to our mission of ensuring everyone in our community has a home through supportive, equitable, and sustainable housing solutions.

Program Overview

Our Veterans’ programs are designed to serve very low-income, primarily homeless Veterans and Veteran families. The program assists Veterans in exiting homelessness and maintaining a permanent housing placement. Services provided by Insight Housing include street and venue-based outreach, case management, permanent housing placement, employment services, and assistance in obtaining VA and other benefits.

Position Summary

The Enrollment & Outreach Supervisor oversees outreach staff responsible for engaging Veterans in the community and facilitating timely enrollment into the SSVF program. This role ensures outreach activities are conducted safely, ethically, and effectively, with a strong emphasis on trauma-informed engagement, trust-building, and Veteran-centered practices. The Supervisor is responsible for meeting outreach and enrollment goals, managing outreach data systems, and removing barriers to program entry by supporting same-day enrollments and streamlined enrollment processes. The Enrollment & Outreach Supervisor reports directly to the SSVF Program Manager.

Essential Duties and Responsibilities

Outreach Staff Supervision & Training
  • Supervise and support Outreach Specialists engaged in community-based Veteran outreach.
  • Provide training and ongoing coaching to ensure staff follow safety protocols and best practices for engaging Veterans.
  • Ensure staff are trained in trauma-informed care, trust-building, rapport development, and ethical engagement.
  • Address performance concerns and support professional growth of outreach staff.
Outreach Planning & Performance Management
  • Map and identify geographic areas of high need and areas with limited or no resources to inform outreach strategies.
  • Establish and monitor daily and weekly outreach goals to ensure consistent engagement activity.
  • Track outreach productivity and adjust deployment strategies as needed to meet program goals.
Enrollment Support & Barrier Reduction
  • Support same-day enrollments whenever possible to reduce barriers to program entry.
  • Identify and implement strategies to streamline enrollment processes and improve access for Veterans.
  • Assist staff with problem-solving enrollment challenges, documentation gaps, and eligibility questions.
  • Collaborate with internal teams to ensure smooth and timely transitions from outreach to enrollment and services.
Enrollment & Data Management
  • Manage and maintain a comprehensive outreach and enrollment database tracking:
    • All individuals engaged or contacted
    • Individuals screened for eligibility
    • Participants enrolled in the SSVF program
    • Individuals screened but not enrolled, including reasons
    • Outreach supplies provided
  • Ensure data is accurate, timely, and audit-ready.
  • Analyze data to identify trends, gaps, and opportunities for improvement.
Inventory & Supply Management
  • Order, track, and maintain inventory of all outreach supplies.
  • Ensure outreach staff are properly equipped to support safe and effective engagement.
  • Monitor inventory usage and maintain appropriate stock levels aligned with program needs.
Compliance & Coordination
  • Ensure outreach and enrollment activities comply with SSVF requirements and organizational policies.
  • Coordinate closely with Case Management and Housing teams to support timely referrals and service linkage.
  • Communicate outreach performance, enrollment outcomes, and barrier-reduction strategies to the SSVF Program Manager

Minimum Qualifications

  • Bachelor’s degree in Social Work, Human Services, Public Health, Sociology, or a related field or equivalent combination of education and relevant experience.
  • Minimum of 3 years of experience in street outreach, community engagement, Veteran services, or homeless services.
  • At least 1 year of experience in a supervisory, lead, or coordinator role with responsibility for staff oversight or workflow management.
  • Demonstrated experience engaging hard-to-reach populations using trauma-informed and Veteran-centered approaches.
  • Strong working knowledge of outreach safety protocols and best practices for community-based engagement.
  • Experience supporting program enrollment, eligibility screening, or intake processes.
  • Proven ability to track performance data and maintain accurate, timely program records.
  • Proficiency with data systems such as HMIS, Excel, Google Sheets, or comparable databases.

Preferred Qualifications

  • Experience working in Veteran-serving programs, particularly SSVF or VA-funded services.
  • Familiarity with same-day enrollment models and low-barrier service delivery.
  • Experience mapping outreach areas or coordinating geographically targeted outreach efforts.
  • Prior experience managing outreach supply inventory and procurement.
  • Experience preparing data or reports for audits, monitoring visits, or funder review.
  • Bilingual or multilingual abilities relevant to the communities served.

Knowledge, Skills, & Abilities

  • Ability to train, coach, and supervise outreach staff in safety, engagement, and performance standards.
  • Strong interpersonal skills with the ability to build trust and rapport with Veterans and community partners.
  • Analytical skills to interpret outreach and enrollment data and adjust strategies accordingly.
  • Ability to manage competing priorities in fast-paced, field-based environments.
  • Strong written and verbal communication skills.
  • Ability to de-escalate situations and model calm, respectful engagement.
  • Commitment to trauma-informed, culturally responsive, and equitable service delivery.

Special Requirements

  • This position requires frequent driving.  A valid California driver license, reliable personal vehicle, current personal auto insurance as required by law, and an MVR sufficient to obtain and reasonably maintain insurability under agency auto liability policies.  
  • Must be able to receive and maintain criminal and credit records clearance. 
  • Must be able to obtain TB clearance