🚀 Head of AI Engineering

About Readily

30% of U.S. healthcare cost is administration. We’re fixing that.

Readily is building the compliance layer for the healthcare industry. Billion-dollar healthcare organizations turn to Readily to analyze regulations, conduct audits, and automate compliance readiness with AI.

We’re the fastest-growing company in this space - 10x revenue YoY. And we’re just getting started.

There’s an old Yorkshire saying: “Where there’s muck, there’s brass.” Healthcare compliance is messy. But in that mess lies an enormous opportunity. If you’re hungry to take ownership and build systems that matter, this is it.

About the Role

We're hiring a Head of AI Engineering to build what an engineering team should look like in the AI era. You'll own the people, the architecture, and the AI systems behind it. This is a hands-on leadership role. You’ll work directly with the founders, who drive company and product vision, while you take the engineering org and AI roadmap as your own. You’ll lead a team of 10-25, set the technical bar, and own how Readily builds - implement all the AI initiatives that will push engineering throughput and product quality.

What You’ll Do

• Reinvent how we build with AI - define what a world-class AI engineering team looks like.
• Lead the design and development of AI tools and systems across engineering teams.
• Optimize and oversee the speed of shipping and quality of products.
• Evaluate and ship new models an agents into production and monitor the costs.
• Partner directly with designers, customer success, product and growth to effect change across the company.
• Hire, mentor, and structure the engineering team while setting and upholding high performance standards.

What We’re Looking For

• AI-pilled: Your default go-to for any problem is AI. You ship with agents regularly and you're already "tokenmaxxing" - building your own agent tooling, and "freeing the claw" to let agents do real work.
• Hunger: High agency, a drive to stay at the edge and do what it takes.
• Efficiency-obsessed: Unoptimized engineering keeps you up at night.
• Intellectually humble: Low ego, high curiosity, collaborative.
• Experienced: 3+ years in engineering management and AI engineering and scaling teams at high-growth startups.

Bonus points: You’re a former founder.

Our Stack

React, Node/Python, PostgresSQL, micro-services, AWS, Azure.

Why Join Readily

• True founding-team ownership.
• Career-defining experience: ship products that rewrite how the industry works.
• Front-row to closing deals with billion-dollar enterprises
• Hyper-growth environment (10× YoY - you’ll feel it).
• A real chance to fix healthcare’s most expensive problem with AI.
• Weekly pickleball 🏓 + a team that loves to win together.

📩 If you want true ownership and define how AI Engineering teams should be built - we’d love to talk.