Design Specialist II – Health & Welfare Benefits Implementations

This is a fully remote position, open to applicants in New York, +2 more states.

📋 Description

• Serve as the main client liaison and strategic operational foundation for a dedicated group of SaaS clients.

• Address intricate technical questions and operational issues through the internal ticketing system.

• Evaluate, test, and identify complex benefits data, eligibility criteria, and platform configuration inconsistencies.

• Deliver actionable written solutions to client administrators.

• Collaborate with Configuration, EDI, and Shared Services teams on elevated escalations.

• Convert complex business requirements into structured functional specifications for development teams.

• Examine backend ticketing and platform patterns to enhance workflow efficiency.

• Develop technical documentation to expand internal knowledge and foster client self-sufficiency.

• Manage competing client demands and adhere to strict response timelines.

⛳️ Requirements

• Bachelor’s degree in IT, Business, or a related field; OR equivalent practical, hands-on industry experience.

• Demonstrated experience in navigating Health & Welfare Benefits administration, open enrollment cycles, or intricate payroll systems.

• Strong ability to analyze system data, identify anomalies, and resolve software issues independently.

• Outstanding written and interpersonal communication skills.

• Capability to clearly communicate technical troubleshooting procedures to corporate HR administrators.

• Solid experience within B2B SaaS environments, case management software, or development lifecycle tools such as Azure DevOps / ADO or Jira.

• High level of data accuracy when reviewing user inputs, system business rules, file feeds, and complex insurance life-event validations.

• Strong organizational skills to balance competing priorities and manage multiple technical tickets simultaneously.

🏝️ Benefits

• Comprehensive total rewards package.

• Paid time off.

• Flexible benefits plan for you and your family.

• Generous company-matched pension.

• Flexible working arrangements with options for remote, in-office, or hybrid work environments.

• Opportunities to give back to the community.

• Career advancement and learning & development opportunities.