Founding Engineer at Pave AI in Chicago

We’re a small, high-performing team of exited founders and industry experts building AI-native software that is transforming how paving contractors operate.

We are achieving market fit, signing multiple paying customers, and are seeing active, real-world adoption. Growth is accelerating, and we’re looking for a Founding Engineer who can independently design, build, and improve production-grade agentic engineering systems with minimal guidance.

This is not a conventional feature-development role. You’ll help define how AI agents reason, use tools, coordinate workflows, request human approval, recover from failures, and take reliable action across real business operations.

You’ll work directly with the founders, customers, and industry experts, turning ambiguous operational problems into dependable agentic workflows. You’ll have significant ownership over the product, architecture, engineering practices, and technical direction of the company.

What you’ll do:

• Design and build production-grade agentic systems from the ground up
• Establish our agentic engineering frameworks, patterns, and development practices
• Build tool-calling, orchestration, planning, memory, approval, and multi-agent workflows
• Create evaluations, guardrails, observability, and feedback loops that make agents reliable
• Develop systems that can handle ambiguity, recover from failure, and operate safely
• Own major capabilities from initial customer problem through production deployment
• Work across AI, backend, frontend, infrastructure, data, and third-party integrations
• Make pragmatic architectural decisions with limited oversight
• Help recruit and mentor future engineers as the team grows

You may be a great fit if you:

• Can take a loosely defined objective and independently turn it into a working production system
• Have hands-on experience building with LLMs, agents, tool use, structured outputs, retrieval, or workflow orchestration
• Understand that reliable agentic systems require more than prompting—including state management, permissions, evaluation, fallbacks, and human oversight
• Have designed or evaluated autonomous and semi-autonomous workflows
• Are comfortable moving across the full stack to deliver complete customer outcomes
• Move quickly while maintaining high standards for reliability, security, and product quality
• Communicate clearly with technical, non-technical, and industry stakeholders
• Thrive in environments with high ownership, limited structure, and minimal guidance

This role is ideal for an exceptional builder who wants founder-level ownership and the opportunity to define how agentic engineering is practiced inside a company with paying customers, validated demand, and strong momentum.