Benefits Specialist

Ironclad is the leading AI contracting platform that transforms agreements into assets. Contracts move faster, insights surface instantly, and agents push work forward, all with you in control. Whether you’re buying or selling, Ironclad unifies the entire process on one intelligent platform, providing leaders with the visibility they need to stay one step ahead. That’s why the world’s most transformative organizations, from OpenAI to the World Health Organization and the Associated Press, trust Ironclad to accelerate their business.

We’re consistently recognized as a leader in the industry: a Leader in the Forrester Wave and Gartner Magic Quadrant for Contract Lifecycle Management, a Fortune Great Place to Work, and one of Fast Company’s Most Innovative Workplaces. Ironclad has also been named to Forbes’ AI 50 and Business Insider’s list of Companies to Bet Your Career On. We’re backed by leading investors including Accel, Y Combinator, Sequoia, BOND, and Franklin Templeton. For more information, visit www.ironcladapp.com or follow us on LinkedIn.

This is a hybrid role based out of our San Francisco office. Office attendance is required at least twice a week on Tuesdays and Thursdays for collaboration and connection. There may be additional in-office days for team or company events.

The Benefits Specialist role exists to deliver a best-in-class benefits experience for employees while ensuring accuracy, compliance, and operational excellence. You’ll manage day-to-day benefits administration, partner with vendors and the People team, and help drive continuous improvements across enrollment, billing, compliance, and employee education. Success looks like high employee satisfaction, clean audits, and smooth annual renewals/open enrollment.

What you’ll do

• 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).

What you’ll bring

• Experience:
  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

• Skills: 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.

• Tools: Hands-on experience with HRIS and benefits admin systems and carrier/broker portals; strong Excel/Google Sheets; familiarity with ticketing systems and document workflows.

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

Nice to have

• 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).

How you’ll succeed in this role

• Outcome orientation: you prioritize employee experience, accuracy, and cycle-time.

• Systems thinking: you design and document processes that scale and reduce rework.

• Data fluency: you use audits and metrics to spot issues early and validate fixes.

• Service mindset: you communicate clearly, handle sensitive topics with care, and close the loop.

Base Salary Range: $122,000 - $153,000 per year

The base salary range represents the minimum and maximum of the salary range for this position based at our San Francisco headquarters. The actual base salary offered for this position will depend on numerous factors, including individual proficiency, anticipated performance, and the location of the selected candidate. Our base salary is just one component of Ironclad’s competitive total rewards package, which also includes equity awards (a new hire grant, along with opportunities for additional awards throughout your tenure), competitive health and wellness benefits, and a commitment to career growth and development.

US Employee Benefits at Ironclad:

• 100% health coverage for employees (medical, dental, and vision), and 75% coverage for dependents with buy-up plan options available

• Market-leading leave policies, including gender-neutral parental leave and compassionate leave

• Family forming support through Maven for you and your partner

• Paid time off - take the time you need, when you need it

• Monthly stipends for wellbeing, hybrid work, and (if applicable) cell phone use

• Mental health support through Modern Health, including therapy, coaching, and digital tools

• Pre-tax commuter benefits (US Employees)

• 401(k) plan with Fidelity with employer match (US Employees)

• Regular team events to connect, recharge, and have fun

• And most importantly: the opportunity to help build the company you want to work at

**UK Employee-specific benefits are included on our UK job postings

Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.