Senior Technical Support Engineer- 6 Months Contract to Hire

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.

• 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 observability across your domain
• Have exposure to engineering and business leadership to strategize what can improve our operational excellence and ability to scale

• You find fulfillment in eliminating root causes and entire categories of problems rather than just fixing isolated incidents.
• You are a natural detective who enjoys tracing complex symptoms across multiple systems to find the source of an issue.
• You value direct visibility into your impact on customers and seeing your work immediately improve the user experience.
• You strive to build leverage and efficiency through the creation of automation and advanced tooling.
• You are energized by knowledge sharing, whether through writing detailed runbooks or mentoring junior Support Engineers.
• You are excited by the opportunity to shape the culture and operational processes of a brand-new function.

• You prefer a 100% predictable workload, as the nature of this role involves responding to incidents and urgent escalations.
• You find rapid context-switching difficult, particularly during on-call weeks that require triaging multiple simultaneous issues.

Please note that this position does not serve as a transition path into Product Engineering at Rippling. If your primary objective is moving into feature development, this career path will not be the appropriate fit.

• Minimum 5-8+ years of experience in support engineering, operations engineering, SRE, or software engineering with strong debugging and operational focus
• Strong debugging skills across web services, queues/async jobs, and data stores — you can trace a failure across multiple services and pinpoint the layer
• Comfort with Python and Go Lang in a large codebase — reading stack traces, adding logging, writing scoped fixes under code review
• Experience with integrations: REST APIs, webhooks, idempotency patterns, API versioning
• Familiarity with MongoDB or document stores and relational data warehouses (Snowflake/BigQuery)
• Excellent written communication suitable for both customer-facing coordination and internal RCA documentation
• Ability to thrive in an ambiguous environment — you are building a new function, not joining an established one
• Infectious passion for solving real customer pain points through systematic operational improvement
• Prior operations engineering, technical support, or forward-deployed engineering experience in a regulated or mission-critical domain
• Experience building runbooks, internal tooling, or operational dashboards

• Benefits or Insurance domain knowledge (Insurance, EDI, LDEX or adjacent concepts)
• Exposure to insurance carriers operations or broker workflows
• Experience with retool or internal admin consoles
• Experience scaling operational engineering practices from 0 to 1