Benefits Operations Special Projects Lead

About the role

Rippling is at the forefront of the AI revolution in business operations, and we’re looking for a visionary Special Projects Lead to redefine how benefits are managed. This isn’t just an operations role; it’s an invitation to architect the future of our Benefits Operations team by embedding AI at the heart of our most critical workflows.

You won’t just be identifying inefficiencies—you’ll be building the solutions that eliminate them. From carrier operations to complex discrepancy resolution, you will have a direct hand in shipping proofs of concept that fundamentally transform team throughput and accuracy. This is your chance to turn manual, high-volume tasks into seamless, automated engines of growth.

This is a dual-focus role designed for a strategist who excels at the intersection of high-impact Business Operations and AI-enabled innovation. We need someone with the sharp, analytical instincts of a management consultant to tackle complex operational challenges, paired with a practical, hands-on curiosity for applying AI to drive meaningful efficiency. You don't need to be technical, but you must be adept at learning new AI tools, understanding their capabilities, and applying them effectively, but you must have the drive to identify high-leverage problems and the follow-through to build the automated solutions that solve them.

What you will do

Size and execute on AI acceleration opportunities — identify high-leverage areas to reduce manual work across benefits ops workflows, conducting cost-benefit analyses to prioritize projects based on potential ROI and impact.

Map and automate high-volume triage workflows — identify the most common root causes behind recurring operational discrepancies, build deterministic resolution paths for cases that don't require judgment, and layer in AI-assisted triage for the rest.

Build and ship proofs of concept — take ownership of end-to-end AI workflows, bring them to production, and measure their impact on team throughput. The goal is working solutions, not slide decks.

Document and scale what works — translate findings into reusable SOPs, Confluence pages, and Loom walkthroughs so the team can understand, maintain, and build on what you've built.

Partner closely with ops leads — embed in the team to understand where manual work is highest, where errors concentrate, and what makes a good automation target. Surface those opportunities and drive them forward.

Build a shared repository of AI use cases — track what's been tried and what's worked across Benefits Ops and adjacent teams, and make it easy for others to build on that foundation.

What you will need

1–3 years of professional experience in business operations, strategy and operations, management consulting, or a similar fast-paced environment.

Bachelor's degree (required).

Genuine curiosity about AI tools and how to apply them practically — prior experience with AI productivity tools is a strong plus, but an engineering background is not required.

Strong analytical and written communication skills, with the ability to break down complex workflows and communicate clearly across teams.

Demonstrated ability to manage multiple workstreams, prioritize effectively, and make progress in ambiguous environments.

A bias toward action — you form a point of view quickly, move without waiting for a perfect brief, and follow through.

Experience in benefits, insurance, or HR tech is a plus but not required.

Additional Information

Rippling highly values having employees working in-office to foster a collaborative work environment and company culture. For office-based employees (employees who live within a defined radius of a Rippling office), Rippling considers working in the office, at least three days a week under current policy, to be an essential function of the employee's role.

#LI_Hybrid

About Rippling

Rippling gives businesses one place to run HR, IT, and Finance. It brings together all of the workforce systems that are normally scattered across a company, like payroll, expenses, benefits, and computers. For the first time ever, you can manage and automate every part of the employee lifecycle in a single system.

Take onboarding, for example. With Rippling, you can hire a new employee anywhere in the world and set up their payroll, corporate card, computer, benefits, and even third-party apps like Slack and Microsoft 365—all within 90 seconds.

Based in San Francisco, CA, Rippling has raised $1.4B+ from the world’s top investors—including Kleiner Perkins, Founders Fund, Sequoia, Greenoaks, and Bedrock—and was named one of America's best startup employers by Forbes.

We prioritize candidate safety. Please be aware that all official communication will only be sent from @Rippling.com addresses.