Benefits Specialist


ContextMedia:Health improves health outcomes for patients, providers and life science companies. We provide technologies incorporating hardware, software and media content that educates, empowers and activates people living with a chronic condition to improve their quality of life. With presence in 25,000 healthcare practices nationally, we continue to scale 265% YOY and have been recognized by Forbes, Crain's and Inc for our culture, business growth and innovation.  

We are a group of creative problem-solvers - with hustle and grit in our DNA - who fight until we win, and do so collaboratively. We believe in communication with transparency, purpose before self and ownership over outcomes. 


The foundation of ContextMedia is our family - the team that we build, develop and grow with. The Benefits Specialist will work closely with the Talent team, specifically our HR Business Partners & our finance team, to support our company’s various benefits programs. This person will lead process improvements, vendor management, and day to day operations for all things benefits. The ideal candidate will be extremely resourceful, solution minded, have a sense of urgency and will understand the importance of prioritization. The ideal candidate will have 4-6 years of experience in a similar capacity.


  • Lead benefit overview meetings with our new hires every 2 weeks
  • Run bi-monthly 401k enrollment meetings and field all 401k questions
  • Monitor enrollment for all benefits for our employees
  • Enroll employees in transit benefits (and any future benefits that do not have a carrier feeds through Paycom)
  • Proactivity monitor our benefits (ex: ensure HSA deductions are correct, ensure no one drops coverage for an incorrect reason, monitor STD/LTD claims, etc)
  • Approve monthly invoices from carriers
  • Process all STD/LTD
  • Monitor leave programs


Please submit a resume and cover letter describing why you'd like to join the ContextMedia family

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