Benefits and Leaves Specialist

About Ramp

At Ramp, we’re rethinking how modern finance teams function in the age of AI. We believe AI isn’t just the next big wave. It’s the new foundation for how business gets done. We’re investing in that future — and in the people bold enough to build it.

Ramp is a financial operations platform designed to save companies time and money. Our all-in-one solution combines payments, corporate cards, vendor management, procurement, travel booking, and automated bookkeeping with built-in intelligence to maximize the impact of every dollar and hour spent. More than 45,000 businesses, from family-owned farms to e-commerce giants to space startups, have saved $10B and 27.5M hours with Ramp. Founded in 2019, Ramp powers the fastest-growing corporate card and bill payment platform in America, and enables over $100 billion in purchases each year.

Ramp’s investors include Thrive Capital, Sands Capital, General Catalyst, Founders Fund, Khosla Ventures, Sequoia Capital, Greylock, and Redpoint, as well as over 100 angel investors who were founders or executives of leading companies. The Ramp team comprises talented leaders from leading financial services and fintech companies—Stripe, Affirm, Goldman Sachs, American Express, Mastercard, Visa, Capital One—as well as technology companies such as Meta, Uber, Netflix, Twitter, Dropbox, and Instacart.

Ramp has been named to Fast Company’s Most Innovative Companies list and LinkedIn’s Top U.S. Startups for more than 3 years, as well as the Forbes Cloud 100, CNBC Disruptor 50, and TIME Magazine’s 100 Most Influential Companies.

About the Role

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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