Benefits Advisor & Operations Specialist - Remote

Overview

At Every.io, we’re reimagining back-office operations for startups. Our platform simplifies finance, compliance, HR, and more - helping founders stay focused on building, not paperwork. We’re a Series A startup backed by top-tier investors, growing fast, and building a world-class team of makers.

If you’re someone who loves turning messy, complex processes into smooth systems that actually work for customers, and you want to see the impact of your work across hundreds of startups - Every is the place to do it.

We’re hiring a Benefits Advisor & Operations Specialist at a pivotal moment: we’re launching our benefits practice and need someone to own both the advisory and operational side of our small group health offerings. In this role, you’ll be both customer-facing and operations-driven. You’ll advise employers on their small group health insurance options, support plan conversations, and then take ownership of the workflows that power Every’s benefits administration. That means preparing and QA’ing group applications, managing renewals and BORs, and leveraging Every’s internal benefits administration tool while quarterbacking issues with carriers, general agencies (GAs), and our partners.

This isn’t just a job. It's a chance to help build Every’s benefits, practice from the ground up, directly impact Every’s customers, and grow with a startup moving fast.

In Short

• Serve as the primary point of contact for customers during benefits setup and renewal.
• Guide employers through plan selection by explaining options across health, dental, vision, and ancillary benefits.
• Communicate directly with carriers to submit group applications, manage enrollments, and resolve issues.
• Ensure compliance with applicable federal and state benefits regulations (ACA, COBRA, etc.).
• Answer employee questions about coverage, eligibility, and enrollment processes.
• Collaborate with Every.io’s payroll and compliance teams to ensure benefits integrate seamlessly.
• Maintain accurate records of plan details, enrollment changes, and carrier correspondence.
• Proactively identify and escalate issues that could impact customer satisfaction or compliance.

Requirements

• 2-4+ years of experience in benefits administration, brokerage, HR, or payroll/benefits SaaS.
• Strong knowledge of group health insurance, including medical, dental, vision, life, and disability plans.
• Experience working directly with carriers and/or TPAs (third-party administrators).
• Customer-first mindset; comfortable explaining complex topics in simple terms.
• Highly organized with attention to detail; able to manage multiple customer cases at once.
• Familiarity with ACA, COBRA, HIPAA, and state-specific compliance rules a plus.
• PHR, SHRM-CP, or CEBS certification a plus (but not required).

Benefits

• Be part of a mission-driven startup solving real problems for founders.
• Work alongside experienced builders in a low-ego, high-ownership environment.
• Competitive comp + meaningful equity.
• Great health benefits, flexible hours, generous PTO.