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OrganizationCareer Support Systems
TypeFull Time
Application DeadlineMay 15, 2026
College Degree Required?No
Salary Range$20-$25/hr
Emailsvogel@careersupport.net
Phone434-879-1715

Description

About CSS
Career Support Systems is a nationally-accredited, community-based organization dedicated to helping people with disabilities and other employment barriers build real, sustainable careers. We do individualized work — no two days, no two consumers, and no two plans look the same.

The Role
This is a field-based position for someone who thrives outside a traditional office setting. You’ll carry a caseload of job seekers, build relationships with local employers, and provide hands-on coaching and support from application through long-term job retention. The work is autonomous, varied, and — for the right person — genuinely energizing.

People come to this role from a wide range of backgrounds: workforce development, education, social services, case management, vocational rehabilitation, retail or hospitality management, and more. What they share is a talent for building trust quickly, staying organized under shifting priorities, and finding creative solutions for people who face real barriers to employment.

Job Duties

What You’ll Do
• Develop and maintain relationships with local employers and community partners to open up job opportunities for the folks we serve
• Conduct individualized needs assessments and build job development plans tailored to each person’s goals
• Support clients through the full arc of employment — applications, interviews, on-site training, and long-term follow-along
• Provide transportation for clients as part of service delivery
• Maintain accurate, detailed electronic documentation of all services

What This Job Actually Looks Like Day-to-Day
This is a community-based role, which means most of your time is spent out in the field — at worksites, employer meetings, and consumer appointments across Charlottesville and surrounding areas. Expect to drive significantly. Mileage and travel time are compensated. A reliable personal vehicle and a clean driving record are required.

Skills Required

What We’re Looking For
• Experience in human services, workforce development, education, case management, or a related field — or a combination of background and drive that translates
• Comfort working independently and managing a shifting, self-directed schedule
• Strong written and verbal communication skills
• Proficiency with MS Office and comfort learning electronic documentation systems
• Experience working with people with disabilities is a strong plus; previous reentry experience is also valued
• Valid driver’s license, reliable personal vehicle, good driving record, and successful background screening

Work Schedule

Work Location: In person | Charlottesville, VA 22902
Shift: Day shift required; some evening availability preferred
Travel: ~75% of working time

No set schedule — this position requires a high level of autonomy and the ability to manage self-scheduled appointments. The candidate would need to generally be available during typical business hours in order to meet with clients in the community.

Additional Info

Compensation & Benefits
• $20.00 – $25.00/hour, non-exempt, plus bonus potential and stipend
• Mileage and travel time compensated
• Health, dental, and vision insurance
• Life insurance
• 403(b) with matching
• Paid time off
• Flexible schedule