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.

Rippling Benefits Overview

The global benefits market is a $5 Trillion GMV spanning healthcare, financial services, transportation, food, and more. Despite its size, it remains deeply fragmented, high-friction, and confusing for every participant:

Employers struggle to choose the right vendors, configure plans, and manage compliance—often requiring entire HR teams to administer benefits.
Employees face unclear, opaque options and poor tools for discovering and using the right benefits for their needs.
Vendors must manually navigate long, costly sales and implementation cycles to reach employers.

Why is the experience so broken?

The largest platforms were built in the late '90s and early 2000s. These incumbents have used their entrenched broker and employer distribution to stifle innovation, leaving the market open for disruption.

Why Rippling Wins

Rippling’s all-in-one HCM suite provides a powerful wedge into this market. By embedding Benefits into our broader platform, we avoid the cold-start problems that hampered standalone benefits startups from winning against established incumbents. We’re now at a scale that we are competing directly with these legacy players and will launch a standalone benefits product in the next couple years to further accelerate our growth. Over the next decade, we will build Benefits into a $2B+ revenue business spanning across 100+ categories.

What We're Building

We are building a multi-sided marketplace that connects:

Employers & Brokers (Demand Side #1)
Employees (Demand Side #2)
Benefit Partners (Supply Side)

Rippling Benefits

Rippling Benefits is a classic multi-sided marketplace that owns our benefits supply platforms, fulfillment ecosystem, benefit partner experience, the benefit categories and product catalog and taxonomy, product plans and pricing and discovery and shopping experience for employers and eventually employees. We are on a journey to platformise and scale the marketplace to build robust, resilient, configurable platforms to include catalog, vendor onboarding and integration, product plans and pricing platforms, discovery - search and recommendations, financial platforms for deductions, reimbursement and settlement, data integrations for accurate audits, reconciliation, reporting and insights, monetisation engine that drives employer sales and employee benefits usage and knowledge, and a data suite for benefit partners and brokers.

Impact

Benefits is the third largest revenue generator for Rippling and recently reached over 20k employers, 500k employees and $50M ARR growing at 40% year on year and well and truly on path to scale over 30+ categories over next 3 years and a billion $ in revenue over the next 5-7 years with the goal to double year over year. We get paid between 2% and 7% of premiums by insurance carriers, 10-20% of revenue by non-insurance partners and draw a PEPY (Per Employee Per Year) average of $20K per employer.

Your Role

As a Senior Staff Engineer, the highest IC role in the Benefits organization,

You would have a comprehensive technical ownership of the Benefits Fulfillment platform and its associated ecosystem which is crucial to Rippling Benefits scaling to a $1Bn+ ARR product over the next 5 years
The purview will encompass a wide range of benefits categories and products, capabilities including, but not limited to, onboarding and integration with a thousands of global carriers, partners and vendors, orchestrating for each employer and employee fulfilment request to the vendors, handling financial transactions such as money movements, payroll deductions, reimbursements and performing reconciliations to ensure data consistency across multiple systems
You would architect tomorrow’s scalable platforms by developing strategic vision for constructing efficient, accurate, highly reliable and scalable infrastructure solutions with full auditability, trackability and traceability
Your role involves designing solutions with right abstractions, unified modelling and driving comprehensive user experiences and end-to-end journeys and being hands-on to lead the way to code them out with the team
You would be expected to explore and implement specialised AI solutions to improve operational efficiencies, increase configurability and address complex industry-specific challenges around data discrepancies and consistencies.
As a technical leader of a growing team of 20 engineers, you would also extend your influence over an engineering organisation of 100+ engineers across Benefits products. You would also drive key initiatives to mentor and grow the Rippling India R&D center, which is expected to grow to 400+ engineers in 2025
You would have the opportunity to build a cohesive technology vision while partnering with Product Managers to build robust products and platforms, Engineering Leaders to promote engineering excellence and shaping team culture.
Your role also requires interfacing with various stakeholders including Operations, Customer Support, Sales and Implementation teams, vendors and cross-functional engineering teams to provide solutions and establish sound long term engineering decisions

Job Description

We are seeking a visionary and hands-on Senior Staff Engineers to join our Benefits Marketplace team, which oversees the entire benefits lifecycle. This role is integral to building reliable, resilient and scalable platforms integrating with thousands of carriers and vendors across our benefits fulfillment ecosystem. We are seeking candidates from leading tech companies who have demonstrated experience in 0-1 and 1-10 scaling journeys, mentoring junior engineers, and working closely with product managers.

You will

Architect and Lead: design, develop, and maintain high scale critical systems. Build right abstractions, models and workflows to work across 40+ growing benefits categories.
Hands-On Coding: actively participate and drive coding and code reviews across complex platforms and systems, using languages such as Python and Golang
Technical Leadership: Provide visionary technical leadership, setting the direction for engineering best practices, shaping team culture and drive adoption of modern technologies and solutions.
System Design: architect systems capable of handling millions of users, ensuring high performance, highly configurable, extensible, reliable and scalable.
AI / ML: lead AI/ML initiatives to drive efficiency, accuracy and feedback loop across carriers and users through intelligent automation, faster onboarding time, innovative solutions to standardize integrations and reduce human involvement and errors
API Development: design and implement clean, modularized abstraction and unified experiences across benefits products and users globally.
Storage Solutions: Design and implement near real-time ETL pipelines for analytical, reporting and intelligence solutions for insights and relational and nosql stores for transactional guarantees crunching through petabytes of benefits data
Mentorship & Culture: mentor and support engineers across the organization, fostering a culture of continuous learning, collaboration, and technical excellence. Shape the team culture on system design, abstractions and modelling, modern tech and AI/ML platforms and adoption.
Observability: Implement comprehensive observability practices, including monitoring, logging, and tracing, to ensure system health and performance.
Collaboration: Work closely with cross-functional teams, including product management, customer support and operations, Rippling core platform and cross functional engineering team to align on strategic goals and ensure successful project delivery.
Documentation and Standards: Develop and maintain comprehensive documentation and standards for system architecture, design, and operational processes.

Required Qualifications

Experience: 15+ years of experience in software engineering, with a significant focus on building large-scale distributed systems and scalable services.
Technical Expertise: Proficient in coding with languages such as Python and Golang. Deep understanding of distributed computing principles, data architecture, and scalable system design.
Leadership: Demonstrated experience in technical leadership roles, with a proven track record of mentoring and developing engineering teams.
Systems Expertise: Extensive experience in building systems handling millions of users in parallel and developing scalable services. Deep understanding of SLAs, system resiliency, and observability.
API Development: Expertise in designing and implementing clean, modularized abstraction APIs and programmatic APIs, including BFF for front-end systems.
Storage Systems: Expertise in both analytical (e.g., Presto, S3, Snowflake) and transactional (e.g., MySQL, Aurora, MongoDB) storage systems.
Cloud and Streaming: Experience with public cloud platforms (e.g., AWS, S3) and streaming technologies (e.g., Spark Streaming, Apache Flink, Kafka Connect).
Workflow Systems: Understanding of both transactional and analytical workflow systems.
Communication: Excellent verbal and written communication skills, with the ability to convey complex technical concepts to diverse audiences.

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