Senior Benefits Administrator

About Open Loop

Open Loop was co-founded by CEO, Dr. Jon Lensing, and COO, Christian Williams, with the vision to bring care anywhere. Our telehealth support solutions are thoughtfully designed to streamline and simplify go-to-market care delivery for companies offering meaningful virtual support to patients across an expansive array of specialties, in all 50 states.

Open Loop is looking for a Senior Benefits Administrator to join our team remotely or at HQ in Des Moines, IA. In this role you will own the design, administration, and ongoing optimization of employee benefits programs, ensuring they are competitive, compliant, and clearly communicated as we continue to scale.

• Support the design and evolution of benefits programs, including medical, dental, vision, retirement, wellness, and ancillary offerings.
• Administer benefits programs end to end, including enrollments, life events, open enrollment execution, and employee support through questions and escalations.
• Manage relationships with brokers, carriers, and vendors; ensure service quality, issue resolution, and effective partnership.
• Lead annual open enrollment planning, execution, and communications.
• Analyze benefits competitiveness, utilization, costs, and trends to inform program design, renewals, and budgeting decisions.
• Support renewals, cost modeling, and budgeting in partnership with Finance and brokers.
• Develop reporting and insights to evaluate program effectiveness and employee impact.
• Ensure benefits programs comply with applicable laws and regulations; maintain accurate documentation, plan materials, and internal controls.
• Maintain accurate documentation, plan materials, and internal controls.
• Create clear, employee-friendly benefits communications and resources.
• Identify and implement process improvements to increase accuracy, efficiency, and employee experience.

• 5+ years of experience in benefits administration and analysis.
• Demonstrated ownership of:
  • Benefits plan administration
  • Open enrollment execution
  • Benefits analysis and renewals support
  • Vendor and broker management
• Hands‑on experience administering benefits within HRIS platforms (e.g., Rippling, Workday), including enrollments, eligibility, and data integrity.
• Strong analytical and problem‑solving skills with attention to detail.
• Ability to balance hands‑on administration with program‑level thinking in a scaling environment.
• Familiarity with benefits compliance and regulatory requirements.
• Experience supporting programs across parent and operating company structures, including multiple legal entities, distinct employee populations, and varying program requirements is preferred but not required.
• Experience in healthcare, telehealth, and/or high‑growth/scaling organizations is preferred but not required.

In addition, for salaried positions you would also be eligible for:

• Medical, Dental, and Vision plans
• Flexible Spending/Health Savings Accounts
• Flexible PTO
• 401(k) + Company Match
• Life Insurance, Pet insurance, and more

We have a relatively flat organizational structure here ryone is encouraged to bring ideas to the table and make things happen. This fits in well with our core values of Autonomy, Competence and Belonging, as we want everyone to feel empowered and supported to do their best work.

Sound like a good fit? We’d love to meet you.