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Ironclad · 5 hours ago

Benefits Specialist

San Francisco, CA

Full-time

Hybrid

Mid Level

$122K/yr - $153K/yr

3+ years exp

Ironclad is the leading AI contracting platform that transforms agreements into assets. The Benefits Specialist role is focused on delivering a best-in-class benefits experience for employees, managing day-to-day benefits administration, and ensuring compliance and operational excellence.

Enterprise SoftwareLegal TechManagement Information SystemsSaaS

Growth Opportunities

Responsibilities

Administer day-to-day benefits operations across health, welfare, and ancillary programs (eligibility, enrollments/changes, life events, COBRA handoffs, and offboarding)

Partner with leave administration vendor to support Cladiators on all available types of leave as well as assisting managers and key stakeholders in navigating leave policies and requirements

Own open enrollment execution end-to-end (project plan, employee communications, system readiness/testing, file validation, and QA on deductions and carrier confirmations)

Reconcile monthly invoices and payroll deductions; investigate and resolve deltas proactively with carriers, brokers, and Payroll/Finance

Ensure compliance with ERISA, ACA, COBRA, HIPAA, Section 125, state leaves, and required employee notices; maintain accurate plan documents/SPDs and audit trails

Resolve employee inquiries with empathy and speed; track themes, SLAs, and root causes to reduce repeat tickets and improve self-serve resources

Partner with vendors/brokers on case management, escalations, eligibility, EDI/file issues, and small plan updates throughout the year

Maintain data integrity across HRIS/benefits platforms; run routine audits between HRIS, payroll, and carrier systems; document controls and SOX-ready processes where applicable

Support annual renewals with plan and census data, benchmarking pulls, communications, and launch readiness

Contribute to benefits education and change management (guides, new-hire onboarding content, manager FAQs, and benefit fair/webinar coordination)

Qualification

Benefits administrationCompliance knowledgeHRIS proficiencyData auditsExcel/Google SheetsDetail orientationService mindsetClear communicationCross-functional coordination

Required

3–5 years in benefits administration at a growth-stage or enterprise company, benefits brokerage/TPA, or HR operations environment

Experience supporting or evaluating self-funded medical plan design and administration, including working with ASO carriers, TPAs, stop-loss arrangements, and interpreting claims reporting

Detail orientation and operational rigor

Employee support with clear written/verbal communication

Cross-functional coordination (Payroll/Finance/People Ops)

Comfort with data audits, spreadsheets, and issue triage

Hands-on experience with HRIS and benefits admin systems and carrier/broker portals

Strong Excel/Google Sheets skills

Familiarity with ticketing systems and document workflows

Working understanding of ERISA, ACA, COBRA, HIPAA, Section 125, and leave/continuation basics (and willingness to deepen expertise)

Preferred

Experience supporting or evaluating self-funded medical plan design/administration (e.g., working with ASO carriers, TPAs, stop-loss, claims reporting)

Exposure to multi-state and/or international benefits coordination and vendor management

Process improvement experience (e.g., EDI/file audits, controls, SOPs, and error-rate reduction)