Lead AI Systems Engineer

This is a fully remote position, open to applicants in United States.

📋 Description

• Take charge of the design and execution of Benepass’s collective internal AI platform and strategy.

• Create platform primitives intended for company-wide utilization, starting with the engineering SDLC and extending to Operations and other internal departments.

• Integrate top-tier AI tools with proprietary systems, various integrations, and shared infrastructure.

• Establish safe compositions of models, tools, contexts, evaluations, secrets, and permissions.

• Develop reusable agents, tool interfaces, retrieval/context layers, workflow runners, observability, and feedback loops.

• Propel AI-assisted coding, reviewing, delivering, CI/CD processes, testing, quality gates, regression detection, and failure triage.

• Evaluate PR and cycle time, adoption rates, developer satisfaction, test speed and signal, and knowledge accessibility.

• Design and implement agentic workflows and knowledge/search systems for engineering and company-wide automation.

• Link agents to repositories, CI, documentation, issue trackers, operational tools, dashboards, and internal systems with necessary permissions and auditability.

• Collaborate with Engineering, Product, Design, Operations, and other leaders to identify and automate high-ROI workflows.

• Supply documentation, reference implementations, guardrails, and golden paths to facilitate adoption.

• Set AI usage standards, evaluation harnesses, data-handling practices, human-in-the-loop controls, and quality metrics.

• Make informed decisions between building and buying, guiding responsible AI adoption to enhance speed, coverage, and quality.

⛳️ Requirements

• Staff-level (or equivalent platform/cross-functional) impact in delivering systems that others rely on.

• Strong programming fundamentals; proficiency in Python and/or TypeScript/JavaScript is preferred.

• Experience in developing internal platforms, developer tools, or automation that integrates into CI/CD.

• Hands-on experience with coding agents, LLM APIs, orchestration, and production operability.

• Experience in driving quality through automation, including E2E/integration testing and intelligent quality gates.

• Solid understanding of systems involving APIs, permissions, observability, and reliability.

• Excellent communication skills with the ability to establish standards and lead multi-team adoption.

• Experience in delivering end-to-end AI systems, encompassing agents, tools, retrieval, evaluations, and integrations.

• Background in full-stack development, developer tools, and/or infrastructure automation.

• Capability to transform ambiguous 0→1 initiatives into structured roadmaps with adoption metrics.

• Bonus: Experience in agentic workflows, evaluation harnesses, RAG/knowledge systems, or operational/workflow automation.

• Bonus: Experience in fintech/regulated domains or ownership of 0→1 platforms in a growth-stage company.

• Must fulfill U.S. employment authorization/sponsorship requirements.

🏝️ Benefits

• Equity

• 95% coverage of medical, dental, and vision

• $250 WFH setup (one-time)

• $500/year Learning & Development Benefit

• $150/month for cell phone + internet

• $100/month for Wellness

• $100/month for Co-working and Commuter Benefit

• Several team onsites each year

• Flexible PTO