Benefits Specialist II

Job Title: Benefits Specialist II
Exemption Status: Exempt
Management Level: N/A
Direct Reports: N/A
Manager Title: Benefits and Wellness Manager
Department: People and Culture
Requisition #: 24387
Pay and Benefits: Estimated hiring range $71,340 – $87,200/ year, 5% bonus target, full benefits.
Posting Notes: This is a fully remote role, but you must reside in one of the listed 9 states.

Job Summary

Under general supervision, this mid-level position is responsible for the comprehensive daily administration of all benefit, retirement, wellness and leave of absence programs for CareOregon and affiliated organizations, in compliance with applicable Federal and State regulations. Primary responsibilities for this intermediate level role include answering employees’ questions related to all benefit, retirement, wellness, and leave programs questions with a high-level of accuracy and attention to detail.

Essential Responsibilities

Leave Administration

  • Administer all leave administration, disability, and accommodation programs and workflows from beginning to end.
  • Update all applicable leave databases and records, including disabling of IS access in accordance with policy, for applicable leaves with accuracy and timeliness.
  • Partner in the development and maintenance of departmental leave processes, including documentation and updating in accordance with regularly requirements.
  • Advise employees and managers on multiple leave laws, company leave policies, state paid leave program workers’ compensation, and short-term and long-term disability benefits.
  • Monitor Leave of Absence and ADA email box communications with third party vendors and managers and respond to inquiries and follow-up upon request.
  • Maintain communication with employees on leave to facilitate smooth and timely return to work; keep managers up to date about employee leaves, changes, and work restrictions.
  • Develop and delivery of educational leave content and resources for employees and managers.
  • Assist with the filing and management of employee worker’s compensation claims.
  • Prepare and audit leave, disability, paid leave and PTO reporting for payroll processing each pay period and respond to payroll follow-up questions and reviews in order to meet payroll processing deadlines.
  • Assist in the development of reports relating to benefits, leave, ADA.
  • Administer the Sabbatical Leave program tracking and approval process.
  • Administer the PTO Donation program.
  • Assist with responding to all federal and/or state requests paid leave program upon receipt.

Benefits Administration

  • Participate in the administration of a comprehensive employee benefits program that includes but is not limited to medical, dental, vision, FSA, HSA, life/AD&D, STD/LTD/IDI, supplemental (e.g., accident, hospital indemnity, critical illness), lifestyle spending accounts, voluntary programs such as pet insurance, legal insurance, ID theft protection, EAP and retirement (401(k), 457(b), and other health and wellness programs.
  • Administration of internally managed or sponsored benefit programs such as, but not limited to, tuition assistance, PTO donation, sabbatical leave, etc.
  • Participate in the annual benefits review process and implementation of all Annual Open Enrollment activities.
  • Assist with the preparation and communication of educational materials and presentation of benefits plan changes for open enrollment, as well as ongoing as needed throughout the year.
  • Build effective relationships with employees and liaise between employees and benefits providers and brokers to explain information on plans, address a variety of issues and matters involving sensitive employee information.
  • Deliver New Hire Benefit Orientation for new hire and newly benefit eligible employees.
  • Respond to routine to moderately complex federal, state, and other inquiries as needed related to benefits (Social Security verifications, medical support orders, etc.).
  • Participate in the administration of CareOregon’s wellness platforms and program.
  • Collaborate with the HR People and Culture Team, for filing employee death claims.
  • Assist in areas related to compliance, testing and reporting performed for all benefits plans, including regulatory filings (ACA), and all legal notifications to employees.
  • Assist with the review, auditing, and submission of payment for all vendor invoices related to benefits and leave.
  • Assist in ongoing process improvements in Benefits and Wellness; remain current on benefits trends and conduct research to evaluate emerging employee benefits ideas.
  • Participate in and/or lead special projects.
  • Provide back-up support to Benefits staff as needed.

Organizational Responsibilities

  • Perform work in alignment with the organization’s mission, vision and values.
  • Support the organization’s commitment to equity, diversity and inclusion by fostering a culture of open mindedness, cultural awareness, compassion and respect for all individuals.
  • Strive to meet annual business goals in support of the organization’s strategic goals.
  • Adhere to the organization’s policies, procedures and other relevant compliance needs.
  • Perform other duties as needed.

Experience and/or Education


  • Minimum 3 years’ experience in benefits administration, to include working with Federal and State protected leave of absence administration and Americans with Disabilities Act (ADA) and reasonable accommodations


  • Experience in the healthcare industry

Knowledge, Skills and Abilities Required


  • Proficient in and have a working understanding of federal, applicable state and local laws, regulations, and statutes relevant to Leave of Absence administration, ADA and reasonable accommodations
  • Proficient knowledge in benefits offerings and administration

Skills and Abilities

  • Strong ability to cultivate and applying knowledge of trends and best practices to daily operations
  • Strong, professional written, verbal and interpersonal communication skills, including the ability to educate and provide concise information to managers, employees, and external partners and vendors at all levels
  • Ability to provide excellent service to internal and external customers and vendors, as well as work collaboratively with other teams within the organization
  • Ability to perform work objectively, being cognizant of fairness and consistency
  • Ability to work well under pressure with frequent interruptions and shifting priorities both independently and collaboratively within a team
  • Ability to balance workload and meet timelines amid shifting priorities and interruptions
  • Ability to handle confidential information and project a positive and professional business image
  • Ability to exercise discretion, independent judgment, and proficient critical thinking skills
  • Strong organizational skills and attention to detail to ensure accuracy
  • Strong computer skills, including Microsoft Office
  • Ability to work effectively with diverse individuals and groups
  • Ability to effectively interact with employees and managers at all levels in the organization (including in a remote environment)
  • Ability to learn, focus, understand, and evaluate information and determine appropriate actions
  • Ability to accept direction and feedback, as well as tolerate and manage stress, and provide escalation support for the Benefits Assistant and Benefits Specialist I
  • Ability to see, read, hear, speak clearly, and perform repetitive finger and wrist movement for at least 6 hours/day

Working Conditions

Work Environment(s):    ☒ Indoor/Office     ☐ Community       ☐ Facilities/Security      ☐ Outdoor Exposure

Member/Patient Facing:    ☒ No                        ☐ Telephonic        ☐ In Person

Hazards: May include, but not limited to, physical and ergonomic hazards.

Equipment:  General office equipment

Travel: May include occasional required or optional travel outside of the workplace; the employee’s personal vehicle, local transit or other means of transportation may be used.

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