ROSALYN FLEMING
Waltham,MA
Summary
Dynamic employment specialist with a proven track record in fostering workforce readiness and essential daily living strategies for diverse individuals. Expertise in conducting thorough assessments, delivering strengths-based counseling, and crafting tailored service plans that drive long-term stability and personal success. Skilled in guiding clients through job search activities and life skills development, enhancing independence and overall quality of life. Recognized for an organized, methodical approach and a steadfast commitment to empowering clients, ensuring effective advocacy and collaboration with multidisciplinary teams to achieve optimal outcomes.
Overview
13
13
years of professional experience
1
1
Certification
Work History
Case Manager
Pine Street Inn
Boston, MA
06.2025 - Current
- Provide individualized employment support to adults experiencing homelessness, addressing barriers to workforce re-entry and long-term stability
- Conduct vocational assessments and develop tailored employment plans aligned with client strengths and goals
- Facilitate job readiness workshops including resume development, interview preparation, and workplace expectations
- Build and maintain employer partnerships to expand job opportunities and advocate for client placement
- Support clients through job search, onboarding, and retention with ongoing follow-up to promote long-term success
- Collaborate with case managers, housing specialists, and community partners to ensure coordinated, holistic service delivery
Employment Specialist
Baycove Health and Human Services
Boston, MA
06.2024 - Current
- Provide employment support to individuals with disabilities, limited work history, and re-entry challenges
- Deliver career exploration, job development, interview preparation, and on-the-job coaching
- Assist clients in identifying career paths, locating job openings, and navigating the application process
- Equip clients with effective interview skills and accompany them to interviews when needed
- Offer post-placement support to ensure successful workplace integration and long-term retention
Customer Agent II – Lead
MDOT Motor Vehicle Administration
Largo, MD
10.2022 - 05.2024
- Managed vehicle titling, registration, driver licensing, and oversight of vehicle-related businesses
- Served as team lead for 20+ agents, ensuring high-quality customer service and timely resolution of inquiries
- Enforced insurance and emissions regulations and investigated non-compliance
- Performed daily financial reconciliation and issued 90+ driver and vehicle products
- Evaluated investigative findings to determine driving privilege eligibility
Case Specialist
Nan McKay
New York, NY
05.2021 - 11.2022
- Supported clients through the ERAP application process and assisted call center staff
- Participated in community outreach on eviction prevention and case management services
- Maintained accurate data entry across multiple systems in compliance with grant requirements
- Reviewed applications, responded to inquiries, and drafted detailed investigative reports
- Evaluated expedited, high-risk, and potentially fraudulent applications
Customer Relations Associate
University of Maryland Global Campus (UMGC)
Largo, MD
11.2012 - 06.2019
- Provided training and guidance to colleagues on clerical and operational procedures
- Led implementation of clerical policies, coordinated quality control, and recommended process improvements
- Analyzed student financial accounts, responded to inquiries, and prepared investigative reports
- Collaborated with Military, Veterans, Financial Aid, and Collections departments
- Worked with Quality Assurance, Fraud, and Compliance teams on process improvement initiatives
Education
Bachelor of Science -
Urban College of Boston
12-2027
Associate of Science - undefined
College of Southern Maryland
MD01-2018
Skills
- Career counseling
- Job readiness training
- Vocational assessments
- Resume & interview coaching
- Employer engagement
- Client Support & Case Management: Daily living skills coaching
- Individualized service planning
- Trauma-informed practices
- Client advocacy
- Resource navigation
- Professional Tools & Systems: Microsoft Office 365
- Case management systems
- Accurate documentation
- Data entry
- Virtual conferencing
- Collaboration & Communication: Interdisciplinary teamwork
- Community partnerships
- Crisis prevention & de-escalation (MANDT)
- Relationship building
Accomplishments
- Achieved stabilization by completing case management with accuracy and efficiency.
Certification
- MANDT – Baycove Organization, 2024
- CPR – Baycove Organization, 2023
- Sensory Inclusive Certification – MLB/Nationals Organization, 2023
- CPI Blue Card – 2026
- Trauma-Informed Care – 2026
Timeline
Case Manager
Pine Street Inn
06.2025 - Current
Employment Specialist
Baycove Health and Human Services
06.2024 - Current
Customer Agent II – Lead
MDOT Motor Vehicle Administration
10.2022 - 05.2024
Case Specialist
Nan McKay
05.2021 - 11.2022
Customer Relations Associate
University of Maryland Global Campus (UMGC)
11.2012 - 06.2019
Associate of Science - undefined
College of Southern Maryland
Bachelor of Science -
Urban College of Boston