Senior Technical Support Engineer- 6 Months Contract to Hire

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. About the Benefits Team at Rippling Employers and employees spend over $5 trillion annually on benefits globally. These include products like health insurance, retirement savings plans, and various other employee benefits that help families navigate critical life decisions. Despite their importance, the benefits industry still needs to be updated, costly and confusing for users. Rippling is transforming this landscape by building the first modern multi-sided marketplace that seamlessly connects brokers, employers, and employees with any benefit. Our platform powers the discovery, purchase, and utilisation of benefits products globally, making the experience easier, more affordable, and user-friendly. Our Benefits Vertical Includes: Benefits Platform: Powers recommendations, payments, and our benefits eligibility engine. Benefits Marketplace: Features over 100 partners, providing various benefits options to meet diverse needs. Rippling Benefits Products: Natively built products that integrate into the overall platform, enhancing user experience and engagement. The engineering team behind the Benefits vertical works on innovative, scalable solutions that shape the future of this industry. This role offers the opportunity to work on complex systems, contribute to impactful projects, and help build the future of benefits at Rippling. We are introducing Support Engineering as a new technical discipline at Rippling — and Benefits Insurance is where it starts. This is a founding role. You will not join an existing team; you will build the function from scratch, define its processes and culture, and set the hiring bar for everyone who comes after you. You will: Own front-line technical triage of carrier integration issues — tracing symptoms from customer tickets through vendor APIs, async job pipelines, data stores, and operational tooling to root cause Confidently resolve complex, multi-system investigations with minimal guidance, and escalate with tight evidence bundles (IDs, timelines, logs, suspected layer) when engineering design changes are needed Debug across Rippling's production stack: Django services, Python & Go lang stack, async job framework (ETA tasks, chunking, callbacks), MongoDB, Snowflake, and carrier vendor APIs Build and maintain runbooks, operational dashboards, alerts, and internal tooling (including Retool workflows) that eliminate entire categories of recurring issues Partner directly with Ops and CX to translate customer symptoms into engineering-quality hypotheses — speaking both customer-friendly and system-precise language Drive measurable improvements in MTTR, ticket backlog, repeat incident rate, and SWE escalation volume across the Insurance domain Establish the Support Engineering function's processes, SLAs, intake taxonomy, and queue governance — you are writing the playbook Provide mentorship to junior support engineers as the team scales, help them grow in their technical responsibilities, and participate in interview loops Drive the standards around operational quality, runbook coverage, and obse