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About the Role
Join Rippling AI as a Staff Software Engineer focused on Agent Assist, an AI-powered product area designed to enhance support agent efficiency and accuracy. This is a high-ownership, lead-shaped role requiring technical depth across AI, product, systems, and operations to identify pain points, create product opportunities, and deliver impactful improvements.
Responsibilities
- Own major technical initiatives for Agent Assist within Rippling AI, from problem discovery through production rollout.
- Build AI-powered workflows to help Support reps answer questions faster, more accurately, and with better context.
- Partner deeply with Support, Support Operations, Product, AI Infrastructure, and Engineering to identify high-leverage pain points and translate them into product and platform bets.
- Create a rapid operating loop: observe support workflows, form hypotheses, ship improvements, measure outcomes, and iterate weekly.
- Convert repeated support questions, failure modes, and operational workarounds into upstream product and platform fixes.
- Design systems that make AI assistance reliable, observable, and controllable in high-stakes customer support workflows.
- Build reusable patterns for context, retrieval, tool use, skills, harnesses, and evaluation that can scale beyond Support into broader Rippling AI surfaces.
- Lead technical direction for a small group of engineers, including architecture, execution planning, code review, and implementation guidance.
- Stay hands-on in the codebase: write production code, debug issues, review critical paths, and make implementation-level tradeoffs.
- Raise the engineering bar by mentoring senior ICs and helping teams reason more effectively about AI-native product development.
Requirements
- 8+ years of software engineering experience, with a strong track record of Staff-level technical leadership and org-wide impact.
- Experience leading complex, multi-engineer or cross-functional initiatives where success required influence rather than direct ownership.
- Strong systems thinking: ability to reason from frontline operational symptoms to root-cause product, platform, or workflow changes.
- Practical AI/LLM fluency, including strong intuition for context windows, retrieval, tool use, skills, harnesses, evaluations, and the tradeoffs involved in building reliable AI workflows.
- Strong product judgment and customer empathy, especially in environments where work materially improved the day-to-day experience of operators, customers, or internal teams.
- Comfort operating in ambiguous, fast-moving environments where the roadmap evolves as the technology, product, and user needs evolve.
- Clear, precise communication with technical and non-technical stakeholders.
- Ability to lead senior engineers, align cross-functional teams, and make progress without perfect ownership boundaries.
Skills
- AI
- LLM
- Context windows
- Retrieval
- Tool use
- Skills
- Harnesses
- Evaluation
- Systems thinking
- Product judgment
- Customer empathy
- Technical leadership
Location
- US-based
Work Type
- Office-based (hybrid)
Experience Level
- Staff-level
- 8+ years of software engineering experience
Salary/Compensations
- Competitive salary + benefits + equity
Benefits
- Competitive salary + benefits + equity
About the Company
- Rippling is building an autonomous operating system for work.
- 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.
Equal Opportunity
- 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 accommodations@rippling.com