Benefits Analyst


Role Description

The Benefits Analyst plays a critical role in the successful administration of the US employee benefits program at Dropbox.  The analyst is knowledgeable of industry and community standards to determine the company's competitive position in employee benefits. This role develops strong relationships our broker/consultant, vendor partners and internal stake-holders in order to efficiently manage the benefit plans and related projects.  The analyst will be tasked with providing guidance and assistance to Dropboxers at all US locations and will be a team steward of customer-centric thinking. 


  • Administer employee benefits programs such as medical, dental, vision plans; life and disability insurance plans; leaves of absence and 401k retirement plan.
  • Work closely with the benefits team, benefits consultants and insurance vendors to implement approved new plans or changes to existing plans by preparing announcement materials, gathering plan summary documents, updating the employee intranet and other media for communicating plans to employees.
  • Act as a subject matter expert for escalation of employee benefits inquiries and complaints to ensure quick, equitable, courteous resolution.  
  • Maintain contact by zoom, phone or email, with insurance companies, employees, and beneficiaries to facilitate proper and complete utilization of benefits for all employees.
  • Craft content and communications for employees that are approachable, succinct and reflect Company culture.
  • Prepare benefits reports for plan audits, actuaries, insurance carriers and management.
  • Lead and act as project manager for the following benefit plans/programs:
    • Compliance management; ensure the program is meeting all legislative requirements including, but not limited to 5500 filings, ACA reporting, SF Health Care Security Ordinance reporting, distribution of required notices.  Continually evaluate and proactively inform on upcoming changes that may impact Dropbox US Benefits administration.
    • Leave of Absence Administration
    • Workday benefits system administration
    • Guardian Dental, Vision, Life/AD&D and LTD
    • Kaiser Medical
    • Federal COBRA
    • And other programs as assigned
  • Co-manage the following:
    • Employee tickets through ServiceNow
    • Bi-weekly onboarding
    • Open Enrollment


  • A bachelor's degree and 35 years of experience in benefits administration
  • Strong customer service skills with a focus on employee education
  • Ability to develop strong working relationships and collaborate with a cross-functional group of partners, both internal and external
  • Proven capability to independently manage projects, including communications and change management
  • Ability to adapt and drive improvements and continuously simplify processes with compliance in mind
  • Comfortable with ambiguity, uncertainty and change
  • Expertise in Workday benefits administration
  • Working knowledge of Excel for reporting and auditing purposes