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Implementation Specialist, Benefits

August 17, 2026

About Rippling Rippling is the first way for businesses to manage all of their HR & IT-payroll, benefits, computers, apps, and more-in one unified workforce platform. By connecting every business system to one source of truth for employee data, businesses can automate all of the manual work they normally need to do to make employee changes. Take onboarding, for example. With Rippling, you can just click a button and set up a new employees' payroll, health insurance, work computer, and third-party apps-like Slack, Zoom, and Office 365-all within 90 seconds. Based in San Francisco, CA, Rippling has raised $1.2B from the world's top investors-including Kleiner Perkins, Founders Fund, Sequoia, Bedrock, and Greenoaks-and was named one of America's best startup employers by Forbes (#12 out of 500). About the role This is an exciting opportunity to be a foundational member of Rippling's Benefits Implementation team! As an Implementation Specialist, Benefits, you will be an implementation partner for brokers and clients. You will be responsible for understanding their technical requirements, building custom insurance plans, and troubleshooting. You will manage an evolving book of business and be the internal go-to for all things related to Benefits. The Benefits implementation team at Rippling is growing- along with our focus on our Brokers and our BenAdmin product. This role offers a unique opportunity to not only implement partners/clients but also work closely with cross-functional teams to build and scale Rippling's Benefits offering. What you will do <ul><li>Become a Rippling Benefits expert - You'll be a go to resource for our brokers/clients within 60 days and a benefits subject matter expert for your Rippling colleagues within 90 days</li><li>Be a trusted implementation partner to our brokers and clients:</li><li><ul><li>You'll need to understand the broker's and/or client's requirements as it relates to insurance</li><li>You'll need to build custom plans within the Rippling environment that meet brokers' or clients' needs. This includes importing enrollment data, reviewing insurance plans and occasionally assisting with deductions issues</li><li>You'll work closely with Implementation and the rest of the Customer Experience organization to ensure the broker and client is set up for success</li></ul></li><li>Partner with our Insurance Ops, Customer Experience and Product teams to evolve our process and product</li><li>Develop and document benefits implementation processes and best practices</li></ul> What you will need <ul><li>A passion and curiosity for all things related to Benefits</li><li>3+ years of experience either in an Insurance brokerage firm or in the Implementation space- specializing in Benefits</li><li><ul><li>A license in Life, Accident & Health or Sickness (Life Agent) is a plus</li></ul></li><li>Strong project management and organizational skills: high attention to detail with excellent time management skills</li><li>Ability to manage broker and client relationship: strong communication and presentation skills</li><li>Self-starter with a bias towards action, energized by a fast-paced environment and excited to build</li></ul> Additional information Rippling is an equal opportunity employer. We are committed to building a diverse and inclusive workforce and do not discriminate based on race, religion, color, national origin, ancestry, physical disability, mental disability, medical condition, genetic information, marital status, sex, gender, gender identity, gender expression, age, sexual orientation, veteran or military status, or any other legally protected characteristics, Rippling is committed to providing reasonable accommodations for candidates with disabilities who need assistance during the hiring process. To request a reasonable accommodation, please email accomodations@rippling.com 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 40 mile 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. This role will receive a competitive salary + benefits + equity. The salary for US-based employees will be aligned with one of the ranges below based on location; see which tier applies to your location here. A variety of factors are considered when determining someone's compensation-including a candidate's professional background, experience, and location. Final offer amounts may vary from the amounts listed below. #li-remote #li-hybrid The pay range for this role is: 71,400 - 113,050 USD per year (US Tier 3) 75,600 - 119,700 USD per year (US Tier 2)

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...