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About TrueLearn

At TrueLearn, we help medical professionals provide the best possible care for their patients. Our learning science–driven platform supports clinicians at every stage of their careers, from board preparation through continuing education. The work we do touches the people who touch patients — which means every line of code, every model, and every experiment we ship has the potential to ripple outward into better care, better outcomes, and better lives.

We are looking for a Senior AI Engineering Manager to help us build the next generation of AI-powered learning experiences. This is a Tech Lead Manager role: you will lead people, shape our agile process and engineering culture, and stay close enough to the code to contribute meaningfully yourself.

The Role

As an AI Engineering Manager, you will own the health and output of a team building AI-powered product solutions at the intersection of learning science and clinical education. You will split your time across three areas:

• People and culture. You will manage, mentor, and grow a team of engineers. You will run 1:1s, support career development, give and solicit candid feedback, and shape hiring. You will be the kind of manager people want to work for — one who builds psychological safety, runs blameless retrospectives, drives buy-in rather than compliance, and treats every teammate as a full human being first.
• Process and delivery. You will shape how the team plans, ships, and learns. You will own agile rituals that actually serve the work (not the other way around), help the team prioritize the highest-impact problems, and create the conditions for fast, sustainable delivery.
• Technical contribution. You will stay hands-on. You will write code, review PRs, weigh in on architecture, prototype with AI tools, and bring opinions about how production AI systems should be built. You should be someone the team trusts technically because you've earned it.

What You'll Do

• Lead a team of engineers building AI-powered features and platforms that serve medical learners and educators.
• Build a team culture defined by trust, candor, psychological safety, and shared ownership — where people feel safe taking risks, naming problems, and disagreeing well.
• Design and evolve agile practices that fit the team and the work, removing ceremony that doesn't earn its keep.
• Contribute directly to the codebase: prototyping, building, reviewing, and helping the team solve hard technical problems.
• Establish and champion best practices for building production-grade AI systems: evaluation, observability, cost and latency management, retrieval architectures, agent design, model selection, prompt and context engineering, guardrails, and the operational discipline that turns demos into dependable products.
• Use AI development tools fluently in your own work and help the team raise its leverage with them.
• Partner with product, design, and learning science content creators to translate ambiguous problems into shipped, measurable outcomes.
• Hire thoughtfully and grow careers intentionally.

What We're Looking For

• 5+ years in engineering leadership, with 2+ years managing teams that shipped AI-powered products to real market success — products with genuine adoption, engagement, and revenue, not pilots that quietly wound down. You've led in high-trust, high-autonomy environments and measure success by your team's growth and your customers' outcomes, not your own visibility. (Help Others Succeed.)
• Hands-on experience designing and operating in probabilistic systems environments — confident when outputs are non-deterministic, requiring evaluation, observability, cost and latency management, retrieval, agents, model selection, prompt and context engineering, human-in-the-loop feedback, and guardrails. You’ve shipped systems that survived contact with real users at scale, and you can speak to what broke and what you'd do differently. (Own the Outcome.)
• A track record of evangelizing AI-native ways of working — driving adoption of AI-assisted development tools, establishing evaluation and experimentation practices, and shifting how teams design, build, ship, and fine-tune. You've changed how a team works, not just how you work. You bring data, evaluation, and learning science into how you build and decide. (Lead with Evidence.)
• Hands-on experience with our core stack — React, Angular, Node.js, and ASP.NET.
• Demonstrated experience establishing repeatable engineering patterns for AI systems at scale — the architectural decisions and operational practices that turn prototypes into reliable products. You direct your team toward the highest-leverage problems rather than the loudest ones. (Make It Count.)
• Fluent daily use of modern AI development tools, with informed opinions about where they help, where they don't, and how to integrate them into a team's workflow. You stay current with a field that changes month over month. (Always Learning.)
• Strong partnership across product, data, and AI disciplines — ability to align engineering execution with AI product strategy, data infrastructure, and domain intelligence, including collaboration on areas such as knowledge graphs, personalization systems, adaptive learning, behavioral analytics, and proprietary data advantages. Your strong written and verbal communication keeps the team aligned and effective across functions.
• A management style rooted in trust rather than authority. You build buy-in, listen well, make it safe to be wrong out loud, and treat humility as a strength.
• Genuine interest in the mission. You don't need a healthcare background, but you should care about the fact that this work matters.

Compensation and Benefits

The base salary range for this role is $200,000–$225,000, plus a 10% annual target bonus. Where an individual offer lands within that range depends on geographic location, relevant experience, and overall fit for the role.

We offer a competitive benefits package, including:

• Comprehensive medical, dental, and vision insurance
• 401(k) with company match
• Unlimited paid time off
• Paid holidays and parental leave
• Fully remote work with a home office setup stipend
• Professional development support
• Life and disability insurance

Why This Role

This is a chance to do engineering leadership work at the frontier of AI, inside a company with a genuinely meaningful mission. You'll help build the systems that help medical professionals learn — and ultimately, help patients get better care. You'll do it with a team that wants to work the way good teams should work: with trust, with rigor, with humor, and with each other.

If that sounds like the kind of work you want to do, we'd love to talk.