Lead AI Systems Engineer

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Benepass

WebsiteLinkedInAll Job Openings

11 - 50 employees

🏥 Healthcare

🛡️ Insurance

👥 HR Tech

💰 $12M Series A on 2021-09

Healthcare • Insurance • HR Tech

Benepass is a flexible benefits platform designed for people-first companies, offering a range of personalized and adaptable employee benefits solutions. With a focus on meeting the diverse needs of today’s global workforce, Benepass allows companies to provide customized benefits packages that include health savings accounts, flexible spending accounts, wellness programs, professional development, and more. The platform emphasizes ease of use with features like card-first technology, automated enrollment, and real-time engagement metrics. Benepass supports companies in designing competitive benefits programs that enhance employee satisfaction and retention while staying aligned with corporate DEI and wellness values.

📋 Description

• Own the design and implementation of Benepass’s shared internal AI platform and strategy • Design platform primitives for company-wide use, beginning with the engineering SDLC and expanding to Operations and other internal functions • Combine industry-leading AI tools with in-house systems, integrations, and shared infrastructure • Define safe composition of models, tools, context, evaluations, secrets, and permissions • Build reusable agents, tool interfaces, retrieval/context layers, workflow runners, observability, and feedback loops • Drive AI-assisted coding, review, delivery, CI/CD, testing, quality gates, regression detection, and failure triage • Measure PR and cycle time, adoption, developer satisfaction, test speed and signal, and knowledge findability • Design and ship agentic workflows and knowledge/search systems for engineering and company-wide automation • Connect agents to repositories, CI, documentation, issue trackers, operations tools, dashboards, and internal systems with permissions and auditability • Partner with Engineering, Product, Design, Operations, and other leaders to select and automate high-ROI workflows • Provide documentation, reference implementations, guardrails, and golden paths for adoption • Establish AI usage standards, evaluation harnesses, data-handling practices, human-in-the-loop controls, and quality metrics • Make build-vs-buy decisions and guide responsible AI adoption that improves speed, coverage, and quality

🎯 Requirements

• Staff-level (or equivalent platform/cross-functional) impact shipping systems others depend on • Strong programming fundamentals; Python and/or TypeScript/JavaScript preferred • Experience building internal platforms, developer tools, or automation integrated into CI/CD • Hands-on experience with coding agents, LLM APIs, orchestration, and production operability • Experience enabling quality through automation, including E2E/integration testing and intelligent quality gates • Solid systems instincts in APIs, permissions, observability, and reliability • Clear communication and ability to set standards and drive multi-team adoption • Experience shipping end-to-end AI systems, including agents, tools, retrieval, evaluations, and integrations • Background in full-stack, developer tools, and/or infrastructure automation • Ability to turn ambiguous 0→1 initiatives into sequenced roadmaps with adoption metrics • Bonus: agentic workflows, evaluation harnesses, RAG/knowledge systems, or operations/workflow automation • Bonus: fintech/regulated-domain experience or 0→1 platform ownership at a growth-stage company • Must address 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 cell phone + internet • $100/month Wellness • $100/month Co-working and Commuter Benefit • Several team onsites a year • Flexible PTO