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Staff Software Engineer - Agent Assist

Rippling
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Hybrid (San Francisco, CA), Hybrid (New York, NY)$189k - $315kFull-timePosted 5d ago

About the role

Staff Software Engineer focusing on Agent Assist within Rippling AI. Lead-shaped, hands-on role to improve AI-powered support workflows, working across AI, product, systems, and operations to make Agent Assist significantly better for Support reps.

Responsibilities

  • Own major technical initiatives for Agent Assist within Rippling AI, from ambiguous problem discovery through production rollout.
  • Build AI-powered workflows that 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 turn 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.

Qualifications

  • 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: you can 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 your 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

Required:Software engineeringAI/LLM fluencySystems thinkingCross-functional leadership

Benefits

  • competitive salary + benefits + equity
  • Office-based collaboration emphasis
  • Pay transparency provided via location-based tiers
Last updated Oct 21, 2026. Interested? Apply on the company site.
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About Rippling

#1 Workforce Management System | HR, IT, Finance

Rippling eliminates the friction from running a business, combining HR, IT, and Finance apps on a unified data platform.

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