Role Overview- We're looking for an Engineering Manager, AI to lead and scale the engineering team building PermitFlow's core agentic infrastructure and evaluation systems.
- This is a builder-leader role. You will own both people leadership and technical execution for the systems that decide whether an AI agent can submit a permit on its own, or needs a human in the loop.
- You will report directly to our VP of Engineering and partner closely with our Product Manager, AI on where the quality bar sits today and what it takes to move it. Our VP strongly values hands-on technical leadership. The best-fit EMs here are deeply technical, comfortable in the weeds of model behavior and eval design, and just as comfortable running a team.
- You will be expected to drive your own roadmap end-to-end from technical direction and execution planning through delivery and measurable accuracy and reliability gains in production, not just shipping features but moving the automation ceiling.
What You'll DoYou will operate across systems, people, and execution at scale:
- Lead and grow an engineering team building and hardening PermitFlow's agentic infrastructure, raising the bar for 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 our Product Manager, AI to define what "reliable enough to submit" means, and build the engineering systems that gate release against that bar
- Build and scale our evaluation infrastructure: golden data sets, LLM-as-judge pipelines, human annotation tooling, and online monitoring for drift and regression
- Drive the internal tooling every team at PermitFlow uses to test, error-analyze, and hill-climb agentic work
- Improve system reliability, observability, and engineering efficiency across our AI stack as usage and jurisdiction coverage scale
- Play a key role in hiring and developing engineers with genuine ML/AI systems depth, and future leaders on the team
What We're Looking ForWe're looking for strong technical leaders who thrive in high-ownership, high-ambiguity environments.
- 5+ years in software engineering, including 1+ year in engineering leadership
- Direct experience building or shipping a production AI/agentic system, not just consuming an API but 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.)
Why This Role MattersThis is not a maintenance role - it is a systems-building role at the foundation of a category being created in real time.
PermitFlow sits at the intersection of:
- fragmented real-world regulatory infrastructure
- high-friction physical economy workflows
- emerging AI systems capable of automating end-to-end complexity
The engineering decisions made here directly determine how much of the permitting process can run without a human in the loop, and how fast housing and infrastructure projects move from idea to execution.
This role offers rare leverage: you'll own both the engineering organization and the core AI infrastructure at an early but rapidly scaling company.
What We Offer- 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)
If you want to build the AI infrastructure connecting software to real-world construction outcomes and help define a category from the ground up, we'd love to talk.
