[Hiring] Benefits Operations Specialist REMOTE USA

Position: Benefits Operations Specialist

Date Posted: March 18, 2026

Industry: Technology / HR / Payroll

Employment Type: Full Time

Experience: 3+ Years

Qualification: Bachelor’s Degree or equivalent experience in Operations, HR, or related field

Salary: $74,000 – $119,900

Location: Remote – USA

Company: Wrapbook

Description:

Wrapbook, a leading platform simplifying production payroll and accounting, is seeking a Benefits Operations Specialist to join their growing remote team in the USA or Canada. This role is critical in supporting the company’s health benefits program for production companies using Wrapbook. The specialist will manage all operational aspects of medical benefits, including onboarding, offboarding, reporting, customer support, and third-party referrals.

Key Responsibilities:

  • Manage operational processes for health benefits, including onboarding, offboarding, reporting, and contribution adjustments
  • Ensure accurate and timely data entry to maintain correct withholding and reporting for clients
  • Offboard employees in the system based on client updates
  • Provide reports to customers and third-party benefits providers
  • Respond to customer inquiries via phone or email and assist internal teams in addressing basic questions
  • Support client onboarding for the health benefits program and mentor Customer Success teams
  • Meet service level objectives regarding accuracy, reporting, case resolution, and benefit adjustments
  • Identify opportunities to improve processes, systems, or product features
  • Review audit reports to ensure accurate benefit eligibility and withholding calculations

Requirements:

  • 3+ years of experience in high-volume operational roles (e.g., fulfillment specialist, operations specialist, benefits advisor), preferably in tech, health insurance, or disability insurance
  • Strong organizational skills, attention to detail, and ability to work accurately at a reasonable pace
  • Comfortable working in an ambiguous, fast-paced environment with a growth mindset
  • Passion for improving customer experience and reducing operational inefficiencies
  • Experience with data entry in proprietary and third-party systems
  • Entertainment payroll experience is preferred but not required

Why Join Wrapbook:
Wrapbook offers a unique environment where technology and creativity intersect. Employees benefit from competitive compensation, comprehensive benefits, and the opportunity to make a meaningful impact.

Benefits:

  • Unlimited Paid Time Off
  • Work remotely anywhere in the USA or Canada
  • Health and dental insurance
  • Up to $1,500 USD / $2,025 CAD for home IT setup
  • Up to 2% matching RRSP / 401K
  • Learning and development opportunities
  • Up to $50 USD / $67.50 CAD for internet/cell phone service

Wrapbook is committed to maintaining a harassment- and discrimination-free workplace, fostering inclusion and safety for all employees.

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