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Engineering Manager, AI

PermitFlow· Engineering
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Hybrid (New York City, NY)$180k - $280kFull-timePosted 1mo ago

About the role

Engineering Manager role leading and scaling PermitFlow's AI agent infrastructure and evaluation systems, owning both people leadership and technical execution to determine when an AI agent can submit permits autonomously and when human-in-the-loop is required.

Responsibilities

  • Lead and grow an engineering team building and hardening PermitFlow's agentic infrastructure, raising ownership, quality, and execution speed
  • Build strong engineering culture through clear expectations, 1:1s, feedback loops, and career development
  • Own the technical architecture behind our workflow agents: orchestration, model serving, latency, cost per task, and failure handling at scale
  • Partner with Product Manager, AI to define reliability thresholds and gate releases against that bar
  • Build and scale evaluation infrastructure: golden data sets, LLM-as-judge pipelines, human annotation tooling, and online monitoring for drift and regression
  • Drive internal tooling used by all teams to test, error-analyze, and hill-climb agentic work
  • Improve system reliability, observability, and engineering efficiency as usage and jurisdiction coverage scale
  • Play a key role in hiring and developing engineers with ML/AI systems depth and future leadership potential

Qualifications

  • 5+ years in software engineering, including 1+ year in engineering leadership
  • Direct experience building or shipping a production AI/agentic system, owning the infrastructure around it
  • Hands-on familiarity with evaluation infrastructure: golden data sets, LLM-as-judge, human annotation, or online monitoring
  • Strong system design and architecture fundamentals, with judgment on when an agent is the right tool and when a simpler system isn't
  • Ability to lead through ambiguity and turn unclear, fast-moving problems into structured execution
  • Deep technical fluency: comfortable in code review, architecture review, and model/system tradeoffs
  • Strong communication skills across technical and non-technical stakeholders, especially product
  • High standards for engineering quality, reliability, and performance
  • Bonus: experience in workflow-heavy, enterprise SaaS, or infrastructure products
  • Bonus: exposure to complex regulated environments (construction, logistics, government systems, etc.)

Skills

Required:Leadership and people managementProduction AI/agentic systemsEvaluation infrastructure

Benefits

  • Competitive salary and meaningful equity in a high-growth company
  • 100% company-paid base medical, dental, and vision coverage for employees + healthcare FSA
  • 401(k) savings plan
  • Unlimited PTO and paid family leave
  • Home office & equipment stipend
  • Daily in-office lunch and dinner provided
  • Commuter benefits (pre-tax transit and parking)
Last updated Sep 30, 2026. Interested? Apply on the company site.
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About PermitFlow

TurboTax for Construction Permitting

Intuitive workflow software that helps general contractors and developers identify the optimal permitting process and needed application forms for a particular project, and then easily fill the relevant paperwork to prepare a robust application package.

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