Benefits and Leaves Specialist

Benefits & Leaves Specialist

We're looking for a Benefits & Leaves Specialist to own and evolve Ramp's global benefits and leave programs. This role will be central to enhancing the employee experience and supporting Ramp's growth by building scalable, compliant, and competitive benefits programs across all geographies.

What You'll Do

Lead the administration of U.S. and global benefits programs, including medical, dental, vision, 401(k), and perks.

Manage all leaves of absence end-to-end (partnering with an external provider on this), ensuring compliant, empathetic, and well-documented employee experiences.

Oversee vendor management to ensure strong partnerships, accuracy, and service quality.

Manage compliance filings and required testing (e.g., ACA, 5500s, nondiscrimination testing) to ensure full regulatory compliance.

Maintain and optimize benefits-related technology and system integrations, ensuring accurate and timely file feeds between platforms / carriers.

Develop proactive benefits communications and employee resources, ensuring information is accessible, accurate, and scalable.

Lead benefits renewals, plan design, and open enrollment processes.

Contribute to global benefits expansion as Ramp enters new markets.

What You Need

4+ years of progressive experience in benefits administration.

Deep knowledge of benefits compliance (ERISA, ACA, HIPAA, FMLA, ADA, COBRA) and leave regulations.

Experience managing vendor relationships at scale.

Strong project management skills with the ability to coordinate multiple workstreams and meet deadlines in a fast-paced environment.

Exceptional attention to detail, with a focus on accuracy, consistency, and process improvement.

Excellent communication and employee relations skills, with an empathetic and solution-oriented approach.

Nice-to-Haves

Experience at a high-growth technology company.

Familiarity with global expansion and international benefits design.

Benefits (for U.S.-based full-time employees)

100% medical, dental & vision insurance coverage for you

Partially covered for your dependents

One Medical annual membership

401k (including employer match on contributions made while employed by Ramp)

Flexible PTO

Fertility HRA (up to $5,000 per year)

WFH stipend to support your home office needs

Wellness stipend

Parental Leave

Relocation support to NYC or SF (as needed)

Pet insurance

Referral Instructions

If you are being referred for the role, please contact that person to apply on your behalf.

Other Notices

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

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