
Job Location Main Plant - San Jose, CA 95112 Position Type Full Time Salary Range $75,000.00 - $85,000.00 Salary/year Travel Percentage Up to 50% Job Shift Day
This is a full-time, in-person position at Goodwill Headquarters in San Jose, CA.
At Mission Services of Silicon Valley, our purpose is simple and powerful: to help people build skills, find meaningful work, and thrive in our community. For nearly 100 years, we’ve been a trusted partner in connecting opportunity with people’s potential. By working hand in hand with local experts, employers, and community members, we create pathways to education, employment, and lasting economic mobility.
As a team, we are committed to:
Empowering one another to do our best work and grow together.
Building strong partnerships and serving as a driving force for economic opportunity in Silicon Valley.
Modeling teamwork, integrity, and cultural intelligence in everything we do.
Acting with mutual respect—for each other, our community, and the environment we share.
The Senior Outreach & Engagement Navigator is a frontline ambassador for Mission Services of Silicon Valley (MSSV), responsible for finding, engaging, and connecting unhoused and at-risk Veterans and jobseekers to critical housing, employment, and stabilization programs including SSVF, HVRP, and SJ Bridge. This role requires deep familiarity with Silicon Valley’s homelessness ecosystem; encampments, shelters, safe parking, THUs, navigation centers, medical respite, and community clinics and a proven ability to build trust with individuals experiencing homelessness.
The Senior Outreach & Engagement Navigator conducts field-based engagement, completes pre-screens and coordinated entry referrals, and works closely with Case Managers, Housing Navigators, Healthcare Navigators, and Career Navigators to ensure every eligible person is rapidly linked to services. This position is ideal for someone who knows the streets, knows the system, and can navigate both with professionalism and empathy.
Job Responsibilities
1. Street & Community Outreach (40%)
Conduct daily outreach to encampments, shelters, THUs, safe parking sites, libraries, hospitals, drop-in centers, and high-activity corridors.
Identify unhoused Civilians and Veterans using direct engagement and by-name list strategies.
Build rapport with individuals experiencing homelessness through trauma-informed, culturally intelligent interaction.
Maintain an active, dynamic outreach route plan aligned with real-time community needs.
Complete pre-screens for SSVF, HVRP, SJ Bridge, and other MSSV programs.
Provide crisis intervention and immediate resource connections during outreach (food, transportation, emergency referrals, warming centers, etc.).
Lead and manage outreach events such as the VA Surge events, Veterans Stand down events and others
2. Engagement, Navigation & Warm Handoffs (30%)
Serve as the first point of contact between participants and MSSV service teams.
Complete initial pre-enrollment tasks, gather ROIs, and support coordinated entry referrals.
Facilitate warm handoffs to CM II, CM III, Housing Navigators, Healthcare Navigators, and Career Navigators.
Assist participants with essential documents (IDs, birth certificates, DD214s, Social Security cards).
Support emergency stabilization activities such as transport to shelters, housing intakes, or veteran services.
Coordinate with VA partners, the County’s CoC, law enforcement outreach teams, EMS/behavioral health mobile units, and community nonprofit partners.
3. Outreach Data, Reporting & Compliance (20%)
Maintain accurate and timely documentation within HMIS, CaseWorthy, or program-specific systems.
Track contact attempts, engagements, locations, and outcomes in alignment with internal performance expectations.
Submit daily/weekly outreach logs and maintain an updated contact roster of encampments, shelters, THUs, and community partners.
Support coordinated entry reporting requirements and contribute to by-name list case conferencing.
Ensure compliance with VA, DOL, City, and County standards, including safety protocols and confidentiality requirements.
4. Partnership & Systems Engagement (10%)
Cultivate relationships with shelters, transitional housing units, day centers, VA outreach teams, county departments, and veteran-serving organizations.
Represent MSSV at community outreach events, resource fairs, and partner meetings.
Participate in case conferencing and cross-functional collaboration with Housing, Employment, Healthcare, and Stabilization teams.
Support MSSV’s federated, integrated service delivery model by coordinating with internal departments and external agencies.
Responsibilities may be added, deleted or changed at any time at the discretion of management, formally or informally either orally or in writing.
Required Qualifications/Experience
3-5 years of experience conducting outreach in homelessness services, veteran services, behavioral health, or street-based engagement.
Demonstrated knowledge of the Silicon Valley homelessness ecosystem, including shelters, interim housing, encampment dynamics, and CoC processes.
Experience working with individuals experiencing homelessness, mental health challenges, substance-use disorders, or trauma histories.
Ability to conduct extensive fieldwork (70–80% of time), including travel across Santa Clara County.
Strong interpersonal and de-escalation skills.
Valid CA driver’s license and reliable transportation.
Proficiency with Microsoft Office, HMIS, and/or case management systems.
Preferred
Qualifications
Veteran status or experience serving Veterans and the unhoused populations.
Bilingual
Knowledge of SSVF, HVRP, SJ Bridge, HUD-VASH, or CoC coordinated entry.
Experience conducting VI-SPDAT, CE referrals, or working from a by-name list.
Familiarity with trauma-informed care, housing-first practices, motivational interviewing, or harm-reduction models.
Equipment Used
Computer, telephone, copy and FAX machines
Skills & Competencies
Deep community knowledge and situational awareness in field settings.
Strong relationship-building skills with participants and external partners.
Ability to work independently and manage dynamic field-based workloads.
Cultural competence, empathy, and strong ethical judgment.
Strong documentation and time-management discipline.
Ability to maintain professionalism in high-stress or unpredictable outreach environments.
Knowledge of highly-utilized locations in San Jose where the homeless congregate and camp
Understanding of and sensitivity to the needs of the homeless
Good problem-solving skills and the ability to prioritize multiple tasks
Ability to work with people of diverse social backgrounds and professional rank
Demonstrated effective communication skills
Knowledge and understanding of community resources and human services
Initiative, flexibility, and the capacity to respond effectively in all situations
Good collaboration skills and the ability to work independently with limited supervision
- Key Performance Indicators
Success in this role will be measured by the ability to:
Lead High-Impact Outreach Efforts to Engage the Unhoused Population
Provide Expert Navigation and Warm Handoffs to MSSV Service Teams
Develop and Maintain Strong Outreach Partnerships & Community Presence
Maintain High Standards of Compliance, Safety, and Data Integrity
Emotional Effort
Moderate: Occasional short deadlines. The work environment is occasionally hectic with occasional high activity, with great emphasis on teamwork.
May work with client suffering with mental illness and/or emotional barriers
Job Setting
The job is performed both indoors and outdoors. There is regular contact with the public, homeless encampments and community agencies. The position will require outreaching in the homeless encampments with minimal supervision.
Physical Requirements
Due to the variety of assignments with this position a person must have the ability to stand, bend, kneel, reach forward and overhead. Standing, sitting, carrying, pushing, and pulling will also be involved.
Work Environment, mainly in-field but this position does have both in-office and outside-office work
Ability to travel to local destination, both by vehicle and on foot
Ability to walk long distance and on rough terrain ( such as trails to creek-side encampments and high traffic areas)
A moderate emotional level effort is required, with occasional high stress with short deadlines.
Mission Services of Silicon Valley is an Equal Opportunity and Affirmative Action Employer encouraging diversity in the workplace. All qualified applicants will receive consideration for employment without regard to their race, color, creed, religion, national origin, citizenship status, ancestry, sex, age, physical or mental disability unrelated to ability, marital status, family responsibilities, pregnancy, genetic information, sexual orientation, gender expression, gender identity, transgender, sex stereotyping, order of protection status, protected veteran or military status, or an unfavorable discharge from military service, and other categories protected by federal, state or local law

Goodwill of Silicon Valley has been transforming lives through the power of work in Santa Clara County since 1928. Goodwill of Silicon Valley's mission is to support our employees, our customers and people with challenging barriers to employment; to raise their standard of living and improve their lives through our services and social enterprise.
We generate revenue and re-invest into the community through programs that give people the tools to live independent lives. We are dedicated to improving employment opportunities, increasing standards of living, providing economic independence, and restoring our clients sense of self value. We do this through workforce creation, vocational training and environmental stewardship.
With 18 retail stores, an online store, an extensive reuse/recycling operation, social enterprise, and our Contract Services division (GoodSource) we help people overcome barriers to employment, build sustainable livelihoods, and transform their lives and communities.