OneSource Virtual (OSV) has worked exclusively with Workday customers since 2008 to deliver compliant, in-tenant technology and expert services to automate the administrative, transactional tasks of payroll, taxes, earned wage access, accounts payable, and benefits. With over 1,500 customers, 92% retention, and $225+ billion in treasury movement annually, OSV helps organizations maximize their Workday investment and operate it with confidence. Payroll, benefits, and finance solutions — all in one place.
The Sr. COBRA Specialist is responsible for supporting the Employee Services Team and utilizing Workday, case management, knowledge base, and contact center technologies and processes. The service teams' functional areas of support include COBRA, Direct-Bill, and Consumer-Directed Health (CDH) Administration.
Responsibilities
Daily File Processing & System Operations
- Review and approve qualifying events triggered by customers via the Workday platform, ensuring accuracy and regulatory compliance.
- Process and audit daily integration files for Qualifying Events, General Rights Notices, Direct Billing, CDH enrollments.
- System Alerts: Review and action system-generated alerts, such as address changes, carrier contact, plans, letters, etc.
Direct-Bill Operations & Reporting
- Process and audit for account changes, terminations, and new account setup, including reporting Direct Bill performance (e.g., enrollments and billing)
Carrier Management
- Process online and manual carrier updates, prepare and send carrier spreadsheets, send haste enrollments, conduct audits, and manage carrier inquiries.
Payment & Member Communication Processing
- Process any review items from the lockbox concerning payment, election forms, and written correspondence.
- Process refunds for requested, remittance, and unallocated balances.
- Research and resolve inbound inquiries from customers or members for member accounts, benefits, second qualifying events, subsidies, and compliance matters.
Project Support
- Support projects operationally with researching, auditing, and completing system updates and member changes as needed.
Process Improvement & Knowledge Management
- Assist in identifying and escalating process gaps for all customers to ensure internal processes are accurate.
- Provide professional and timely service to internal and external requests.
- Escalate to a Supervisor when the knowledge base or tools are insufficient to satisfy inquiries.
- Form strong partnerships within the department and organization.
- Identify and document areas of improvement or innovation through process change or automation.
- Assume ad-hoc duties as assigned by Manager.
Competencies
- Experience working within the Benefits Administration industry, including employee benefits, eligibility, enrollment, billing, reconciliation, COBRA, Consumer-Directed Health, and customer support processes.
- Effective communication skills via telephone, email and in-person.
- Must be willing to adapt and display positive attitude.
- Ability to work independently and as part of a team.
- Continuous improvement mindset, actively engage in company, team, and departmental activities, contributing ideas, sharing knowledge, and supporting initiatives.
- Demonstrate resilience and the ability to remain focused, organized, and productive in fast-paced environments with multiple deadlines and competing demands.
- Must value and promote team spirit, have outstanding interpersonal skill set; exhibit professionalism within the workplace.
- Maintain punctuality and adherence to the set schedule with overtime hours as needed.
- Able to manage member information while maintaining confidentiality.
- Analytical skills; strong research and follow-up skills.
Qualifications
Education/Certification Requirement
High School diploma
Required
- 3-5 years of related experience and/or training, 1 year min as Specialist strongly preferred.
- Proficient PC Skills (HRIS, Microsoft Excel, Word, Outlook, Adobe, etc…)
- Strong written and verbal communication skills.
- Comfort working in systems-heavy environments, using shared trackers and case management platforms.
- Strong organizational skills with the ability to manage multiple priorities and drive follow-through.
- Strong attention to detail and problem-solving abilities.
Preferred
- Bachelor’s degree.
- Experience with Consumer Driven Healthcare administration.
- Experience analyzing employee benefits, eligibility, enrollment, payroll, billing, or carrier data to identify discrepancies and support administration activities.
- Experience using Workday software.
- Experience using Alegeus WCC or WCA software.
- Experience using Salesforce or similar case-tracking / workflow systems.
#LI-REMOTE
You are encouraged to learn and share ideas when you join the OneSource Virtual team. We reward innovative thinking, fresh perspectives, creative collaboration, and hard work. As an organization experiencing routine strategic growth, we are always on the lookout for intelligent, talented, and forward-thinking professionals to join our team. OSV employees enjoy a values-based culture, upward mobility, and professional development with opportunities of all kinds.
Similar Jobs
What you need to know about the San Francisco Tech Scene
Key Facts About San Francisco Tech
- Number of Tech Workers: 365,500; 13.9% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: Google, Apple, Salesforce, Meta
- Key Industries: Artificial intelligence, cloud computing, fintech, consumer technology, software
- Funding Landscape: $50.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Sequoia Capital, Andreessen Horowitz, Bessemer Venture Partners, Greylock Partners, Khosla Ventures, Kleiner Perkins
- Research Centers and Universities: Stanford University; University of California, Berkeley; University of San Francisco; Santa Clara University; Ames Research Center; Center for AI Safety; California Institute for Regenerative Medicine


