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Senior Benefits Specialist

Date: Nov 15, 2021

Location: San Diego, CA, US, 92108 Los Angeles, CA, US, 9001 Orange County, CA, US, 92859 Long Beach, CA, US, 90806 Riverside, CA, US, 92501 Sacramento, CA, US, 95652 San Bernardino, CA, US, 92410

Company: Wawanesa Insurance


We’re proud to give our employees the flexibility to choose how and where they want to work. In this role, you will decide whether your preference is to work from home, work from the office or a hybrid of time spent at both. You may live and work in any state where Wawanesa currently operates in the U.S.

Wawanesa Mutual Insurance is one of the largest property and casualty insurers in Canada with $3 billion in annual revenues and assets of more than $9 billion. Wawanesa Mutual, founded in 1896 with executive offices in Winnipeg, is the parent company of Wawanesa General, which offers property and casualty insurance in California and Oregon, and Wawanesa Life, which distributes life insurance products and services throughout Canada. With over 3,500 employees, Wawanesa proudly serves over two million policyholders in Canada and the United States. Wawanesa actively gives back to organizations that strengthen communities where it operates, donating well above internationally recognized benchmarks for excellence in corporate philanthropy.

We are currently looking for dedicated, driven, and enthusiastic individuals who thrive in an environment that welcomes change and are looking for an opportunity for diverse experience and advancement on a growing team.


Job Overview

Working under general supervision, the Sr. Benefits Specialist supports Wawanesa General Insurance objectives by managing employer sponsored benefit programs inclusive of health and welfare benefits, workers compensation, ergonomics, educational assistance plans, and leaves of absence.


Job Responsibilities

  • Oversee third party administrators of employee disability, leaves and pay programs inclusive of FMLA, CFRA, PDL, STD, LTD, PFL and other leaves required by state and federal law inclusive of communicating with external agencies, Executive Office, payroll and supervisors regarding employee status.
  • Manage electronic employee benefit enrollments and changes inclusive of medical, dental, vision, long term care, flexible spending, employee assistance program and early retirement healthcare.
  • Manage benefit communications inclusive of approval of benefit materials, conducting orientation with new hires, and ensuring compliance with government-mandated disclosures.
  • Manage Workers Compensation program inclusive of supervising adjusters, third party medical providers, insurance carrier and Broker.
  • Lead annual open enrollment and benefits renewal process inclusive of attending meetings, compiling census data, organizing and coordinating benefits enrollment meetings and distributing materials.
  • Manage company-wide ergonomics program inclusive of ensuring work station evaluations are conducted and documented and necessary equipment is in place for employees. Manage relationship with third party ergonomic vendors as required.
  • Process payment of benefit invoices inclusive of reconciling charges, resolving discrepancies, and submitting and approving for payment in a timely manner.
  • Resolve all escalated concerns from employees in regards to their benefits and leaves and ensure quality of service received from carriers and Third Party Administrators.
  • Maintain up to date knowledge of benefit and leave of absence regulations and trends and make recommendations for changes when needed.
  • Oversee HR Assistant in the administration of our Education Assistance Program.
  • Act as backup for other positions within the department as needed, inclusive of front desk support, HR compliance, and general HR support.
  • Perform other duties as assigned.




  • 5 years experience handling benefits and leaves for a medium sized company (200+ employees) required
  • Expert knowledge of federal and state regulations that pertain to healthcare, leaves of absence and other employer sponsored benefit programs
  • Intermediate knowledge of Microsoft Office Suite, inclusive of Word and Excel, sufficient to develop documents and spreadsheets for tracking and archiving information.
  • Ability to maintain strict confidentiality when working with sensitive data.
  • Basic math skills sufficient to calculate health and other general benefit invoices.
  • Strong written and verbal communication skills with the ability to create detailed accurate presentations and present in front of a group.
  • Ability to effectively manage time, multi task, work under pressure, and meet deadlines.
  • Possess high degree of accuracy to proof and verify the correctness of information.
  • Strong interpersonal skills with the ability to interact with internal and external stakeholders.
  • Solid investigative and analytical skills sufficient to resolve routine and repetitive administrative problems and employee concerns.
  • Knowledge of accessing information via the Internet.
  • Position requires the ability to lift up to 10lbs on a daily basis and a low degree of mobility throughout the branch buildings to meet internal customer demands.

Wawanesa General Insurance Company is an equal opportunity employer and is committed to a diverse workforce. Wawanesa provides equal employment opportunity to all employees and applicants without regard to an individual’s protected status: race/ethnicity, color, religion, creed, sex/gender, sexual orientation, gender identity/expression, marital status, pregnancy/childbirth or related conditions, national origin, disability, military or veteran status, or any other protected status.  If you are a qualified individual with a disability, you have the right to request a reasonable accommodation to assist in the application process. Reasonable accommodations are also provided for other protected reasons such as religious creed. You may request reasonable accommodations by calling the Human Resources department at 858-874-5404 or emailing Human Resources at

If you are interested in this exciting, challenging position with Wawanesa, apply today with your Resume.

Nearest Major Market: San Diego