Jellyvision is hiring a

Benefits Administrator



We here at Jellyvision are the proud parents of ALEX®, an interactive employee communications platform that happens to share some DNA (and a sense of humor) with the smash-hit trivia video game YOU DON’T KNOW JACK®, created by Jellyvision's founder. ALEX makes navigating tricky decisions—like choosing and using employee benefits or improving your financial wellness—easier, faster, and more helpful, not to mention entertaining. The success of the ALEX platform has exceeded our wildest dreams, (except for the part right before we woke up where our mom was riding a giraffe), which is why we need talented folks like you to help us help ALEX take over the world…er…continue to grow and succeed.


We’re looking for an incredibly organized, creative, get it done, kind of person with great communication skills to join our team.  We are constantly evaluating our benefits offerings and we need someone who will innovate, tweak, seek feedback, rinse and repeat, all while administering our benefits with great care.  Specifically, your responsibilities will include: 

  • Administer various benefits programs including medical, dental, vision, disability, life insurance, HSA/FSA plans, and 401k.
  • Serve as primary liaison for benefits related questions from employees. When necessary, work with benefit providers and brokers to quickly resolve employee inquiries.
  • Ensure 401(k) plan compliance by performing requisite testing, regulatory filings, and leading the annual 401(k) audit.
  • Analyze premium invoices to ensure that costs are appropriate and enrollment is correct.
  • Maintain benefits information in All The Places (internal wiki, ALEX, payroll system, etc).
  • Orchestrate all benefits changes related to onboarding and offboarding.
  • Play a key role in annual renewal process including strategy discussions and plan design.
  • Manage all aspects of open enrollment, including communication, system set up, enrollment review/audit.
  • Develop and direct various wellness initiatives throughout the year.
  • Research and analyze benchmarking data to ensure that benefits plans are cost effective and competitive.
  • Monitor and research benefit trends.
  • Provide ongoing benefits support and education to employees.
  • Figure out how our benefits programs can be improved and/or more efficient.
  • Assist periodically with payroll. 


  • The obvious qualities: whip smart, professional, responsible, dedicated, friendly, flexible, patient, and enthusiastic.
  • An amazing communicator. In person, on the phone, and in writing. You will be communicating all day every day – in faces, on email/slack, one on one, en masse. Your communication skills really need to be excellent, and with our very own Jellyvision specific voice
  • Analytically inclined. Someone who is constantly digging into the data (usage, costs, trends, service, coverage, effectiveness, surveys, spreadsheets) to determine how to tailor a plan that best fits our needs.
  • A true people person. And we don't just mean someone who can talk to anyone - being a great listener is actually more important in this role. You need to love learning by Q&A – asking the right questions and then listening carefully to the responses to understand what concerns and delights employees
  • Strong ethics and discretion. You will have access to a great deal of confidential information and must act as a steward of ethics and discretion when it comes to handling sensitive information.
  • A sense of humor is a must. Interesting or unusual hobbies and tastes in music is a plus.


  • Minimum of two years’ work experiencein a related position
  • Solid knowledge of benefits regulations, systems, and processes.

ANYTHING ELSE?  We share a commitment to excellence and a desire to work in a comfortable, friendly atmosphere, so we only hire nice, bright, funny people who are willing to work hard.  Our credo is a simple one: be helpful. And we think we can be most helpful if our workforce is as diverse in thought, perspective, and culture as the people who use our products. We are looking to add amazing folks to our team who will bring diversity across many lines, including race, ethnicity, religion, sexual orientation, age, marital status, disability, gender identity, sex, and country of origin. 

ARE THERE ANY PERKS? Yes, we love perks.

  • Competitive pay, 401(k) with matching and benefits. We pay 100% of the cost of premiums for medical, dental, vision, disability and life insurance for our employees (as long as you qualify for our tobacco-free discount; if you’re a tobacco user, your medical premiums will be higher than $0). We also cover a really nice chunk of the cost of premiums for spouse/dependent medical, dental and vision insurance.
  • Casual dress and a flexible schedule. Come in a sweatshirt, jeans, whatever, like everyone else here.
  • Creative work environment. We are lucky to work in a place that is full of intelligent, talented and innovative folks. Although most hours the place is deathly quiet (we're a focused bunch), this is punctuated with hilarious outbursts and general merriment, which makes a nice way to spend the day.
  • Charitable match and events. Like giving back? Like eating dips/baked goods and listening to music? JV matches up to $100 per employee to a single charitable organization once every calendar year! We also find fun ways to give back as a community to a variety of organizations that are important to us, by putting on charitable events such as bake sales, dip fests, battle of the bands, where all the money collected by our people goes to the organization that is being promoted! Giving back is important to us, so why not do it in a way where we can eat goodies?
  • Free food. Every week, we stock our kitchen with free healthy snack foods, and we have a catered lunch every other week to give people a reason to hang out and eat together.
  • Easy transportation and lots of love for folks who bike to work. We’re really close to the North/Clybourn red line stop and the Halsted (#8) bus (right by the Apple Store and Mega Whole Foods too), and we have a transit FSA that allows you to dedicate pre-tax dollars to public transportation expenses. A number of our employees like to bike to work, so we also have bike storage, showers and lockers in the office. And for those without their own bike in the city, we offer free divvy memberships – complete with Jellyvision bike helmets you can borrow from the office.
  • Did we mention our yoga and meditation classes? We bring a pro instructor right to the office. Fully subsidized by Jellyvision and fully optional, btw.
  • Oh! And we have a massage chair. Not just any massage chair, my friend. It’s the Renew 2 Zero-Gravity Massage Chair by Brookstone®. Feeling a little stiff? Sit down. Relax. Feel better? Good. Okay, back to work.


We look forward to hearing about you and what you do. Make sure your application includes:

  • cover letter that highlights three reasons you think you’d be great for the gig, focusing on how your past experience has prepared you for this kind of position. Writing is key to all we do, and we weigh cover letters heavily. We love a cover letter that really shows us your personality (check out our company bios to see the wide range of personalities we’ve already got in house), but don’t stress if you’re not a comedian. You don’t have to be funny. Just be yourself. We’re mostly interested in learning who you are, what you love to do, and why you’d love to do it here with us.
  • Your resume 

You will receive an auto-reply confirming that we've received your application.

Please know that every single application we receive is read by a real live human being. However that kind of thoughtful review takes time, so it may take us a little while to get back to you (but we will, we promise). In the meantime, NO FOLLOW UP PHONE CALLS OR EMAILS, PLEASE. It’s not that we don’t love hearing from you. It’s just that time spent responding to follow ups could be spent…well…reading your application. Please rest assured that if you received a confirmation from Recruiting Robot, we’ve got your application, and will get back to you really soon. We knew you’d understand.

If you still have pressing questions in the meantime, please feel free to check out our handy-dandy FAQ page!

Thanks for your interest in Jellyvision!





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