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Benefits Manager

Remote (or Columbus, OH)

The Position.
Our small but mighty HR team caters to over 1500 Root employees. We are seeking a knowledgeable, meticulous Benefits Manager with a persisting "employee as the customer" mindset. This person will aid in our mission of creating a work environment conducive to solving tough problems as Root continues to scale (in employees, locations, and business initiatives). It's imperative that this person has a deep understanding of regulatory requirements (and is ready for roll-up-your-sleeves research when presented with a unique situation) as we welcome new employees from a variety of locations.
The Benefits Manager is an individual contributor position on our People Team that will report to the Sr Director of Total Rewards. Manage day-to-day plan administration for all U.S. employee benefits including medical, dental, vision, life, disability, COBRA, FSA, HSA. 401(k) and any other employee benefits programs offered at Root.

What you'll be doing.

  • Manage day-to-day plan administration for all U.S. employee benefits including medical, dental, visions, life, disability, COBRA, FSA, HSA, 401(k), and any other employee benefits programs offered at Root
  • Manage the day-to-day relationships with key vendors and internal partners
  • Project manage medical plan projects such as RFPs, implementation of vendor changes and/or plan design changes. Ensure alignment across key milestones and program deliverables, including all privacy, legal, security and related requirements are met
  • Manage special projects including impacts on benefits and Annual Enrollment testing to ensure proper plan set up
  • Lead annual enrollment process including technical administration, vendor coordination, and the review of communication strategy
  • Oversee applicable benefit plan audits and 5500 filings
  • Monitor employee benefits and retirement plans vendor reports and recommend plan design changes to address identified trends. Use data analytics to ensure understanding of impact and outcomes
  • Support SPDs, SBCs, benefit communications, and other plan documents to ensure that all plan provisions are accurately reflected
  • Assure compliance with laws and regulations governing employer-sponsored benefit plans such as ERISA, HIPAA, Affordable Care Act (ACA), etc.
  • Review state and federal laws pertaining to Root’s benefits plans, analyze impact of any changes, and provide recommendations to leadership where applicable
  • Ensure compliance of benefits and retirement programs and coordinate the preparation of regulatory filings with federal and state agencies including IRS and DOL
  • Manage day to day 401(k) plan administration including timely funding of payroll and match contributions, coordinating the annual audit and 5500 filing, all regulatory employee communications, and timely resolution of employee escalations
  • Establish and maintain collaborative relationships with key benefit stakeholders across the organization (e.g. payroll, finance, legal, HR People Team) to support benefits administration and ensure efficient plan communication, administration and excellent customer service to employees

What we're looking for.

  • 10+ years of experience supporting benefits administration within an organization
  • Benefits design/strategy experience a plus
  • Excellent written and verbal communication skills
  • Experience with Workday HRIS Solution
  • Ability to work well with others in a fast-paced, dynamic environment
  • Ability to use Google suite of applications
  • Experience using Spoke and Slack a plus
  • Knowledge of automated systems which provide the first line of support for employee questions
  • Excellent critical thinking skills
  • Must be a self-directed and motivated team player with strong attention to detail

Get In Touch

Finding the right people to help us build Root is a top priority. Whether you would like to explore the possibility of working together or simply learn more about the position, we’d love to hear from you!

Apply now

Join us

At Root, we judge people based on the merit of their work, not who they are. If you are passionate about what this role entails and solving real problems, we encourage you to apply. We want to learn about you and what you can add to our team.

Who we are

We’re harnessing the power of technology to revolutionize insurance. Using machine learning and mobile telematic platforms, we’ve built one of the most innovative FinTech companies in the world. And we’re just getting started.

What draws people to Root

Our success is in large part due to our unwavering standards in hiring. We recognize that our products are only as good as the people building and promoting them. We want individuals who find solutions by going through the cycle of ideation to implementation with curiosity, rigor, and an analytical lens. Ask anyone who works here and you’ll hear similar reasons for why they joined:

Autonomy—for assertive self-starters, the opportunities to contribute are limitless. Impact—by challenging the way it’s always been done, we solve problems that have a big impact on our business. Collaboration—we encourage rich discussion and civil debate at every turn. People—we are inspired by the collection of crazy-smart people around us.

Open positions


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Research & Development

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Root Inc.

80 E. Rich Street

Suite 500

Columbus, OH 43215

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