Managing Director of Technology - Chicago

Location: Remote (U.S. or Canada)

Type: US Applicants – Full-Time; Canadian Applicants – Independent Contractor

**A note before you read further**

The world is changing fast, and so is this role. We can't fully tell you what this job looks like in six months. That's true of every role at Human Agency right now. What we need from you, no matter what: accountability, curiosity, and a builder-first mindset. If that sounds exciting, keep reading. If it sounds intimidating but you're still interested, let's talk. If none of that sounds like you, that's okay. This probably isn't your spot.

About Human Agency

We're scaling rapidly and have a growing pipeline of opportunities that demand exceptional talent across disciplines. Our mission is to bring on individuals, from creative producers to technical experts to entrepreneurial leaders, who can help us realize this next chapter of growth.

We are a company of doers. Leaders roll up their sleeves, teams work flat, and everyone contributes to what ships. Titles don't insulate us from feedback or basics. We invite critique, learn quickly, and keep raising the bar. The best ideas win here, no matter where they come from, because clients trust us to deliver the strongest outcomes every time.

Our clients' missions, products, and bottom lines are sacred. We immerse ourselves in their world, becoming stewards of their goals and partners in solving big problems. Every product, strategy, or asset we create must be both beautiful and functional; practical, usable, and designed for real-world impact.

Humans are our most valuable resource, and we only grow by hiring people who push us forward. Across strategy, engineering, design, data, and operations, we seek out teammates who raise the bar and make us better. Always hire up, never down.

We partner with organizations of all sizes to explore, design, and implement AI strategies that are secure, scalable, and human-centered. We believe AI should amplify human potential, not replace it, and we build with that conviction in every engagement. From advisory and tooling to implementation and education, we meet clients where they are and help them integrate AI in ways that align with their mission and values. Our goal is to empower teams to work smarter, move faster, and unlock new possibilities through thoughtful, responsible innovation.

And through it all, we lead with purpose, love, and adventure. We do meaningful work with people we care about, and we make the ride an adventure worth taking. Because at Human Agency, who we are and how we work are one and the same.

The Opportunity

Human Agency is an AI-native consultancy that builds, ships, and operates alongside our clients. We don’t advise from the sideline — we embed inside enterprise organizations and deploy production AI systems that do real work.

Our current anchor engagement is inside one of the largest privately held construction enterprises in the United States — LLM orchestration, document intelligence, workflow automation, enterprise integration. Not strategy decks. Not innovation labs. Systems that run.

We need a Managing Director of Technology to own the technical side of the house as we scale Human Agency. That means leading client delivery, making architecture calls, building the engineering team, and being the technical voice in rooms with C-suite executives. You’ll work closely on strategy with both the Founder and the Managing Director of AI — but the technical execution, the team, and the platform are yours.

This role requires someone who can move between writing production code and presenting to a client’s CEO in the same week. If that sounds like whiplash, this isn’t the right fit. If that sounds like Tuesday, keep reading.

What You’ll Do

Lead technical delivery for enterprise clients. You’re the most senior technical person in the room on our biggest engagements. You decide what’s feasible, design the architecture, and make sure it ships. When a client executive asks “can we do this?” — you’re the one who answers.

Build how we deliver, not just what we deliver. One client engagement works because of talented people and brute effort. Ten engagements work because of systems. You design the repeatable model — how we scope, staff, build, and deploy — so the team can run engagements without you in every meeting. That means building discovery frameworks, reference architectures, deployment templates, and evaluation routines that actually get used.

Hire and develop the engineering team. You set the bar, own the pipeline, and make the calls on who joins. We need people who can build with high autonomy in ambiguous environments, and you know how to find them. You also know how to make good engineers better through architecture guidance, code review, and honest feedback.

Own platform and infrastructure decisions. Build vs. buy, tooling, deployment, security — you make the calls. A Principal Engineer handles day-to-day infrastructure execution; you set priorities and architectural direction.

Shape our AI strategy through the lens of what actually ships. You have real opinions on LLM orchestration, RAG, agents, evaluation, and fine-tuning — formed by building things, not reading about them. You decide which technical bets we make and which we skip, based on what creates value for clients, not what looks good on a slide.

What We’re Looking For

• You’ve built and shipped AI/ML systems in production. Not prototypes. Not demos. Things that run and that people depend on.
• You’ve hired and led a technical team — at least 5 people, ideally more. You’ve seen what breaks when a team grows and you’ve fixed it.
• You can explain a technical trade-off to a non-technical executive in a way that helps them make a decision. You’ve done this in high-stakes settings.
• You have strong opinions on AI architecture grounded in hands-on experience — and you change those opinions when the evidence says to.
• You’re comfortable in the weeds. When something is broken or a team is stuck, you get in and help, not schedule a meeting about it.
• You know your way around cloud infrastructure and engineering practices well enough to make platform calls with confidence.

Bonus points for: you’ve scaled a startup or early-stage company before — built the team, built the systems, lived through the growing pains; experience in a services or consultancy model (SOWs, staffing, client delivery); a network of engineers you’ve worked with and would hire again.

You Should Apply If

• You’d rather build AI systems than talk about AI strategy
• You want to own a technical organization, not manage a lane inside someone else’s
• You’re comfortable making big decisions with imperfect information — and owning the outcome
• You want to work somewhere with real revenue, real clients, and real problems to solve
• You’re energized by building a company — not just writing code, but shaping how the whole thing works

You Should Not Apply If

• You want a CTO-like title with a strategy focus and minimal hands-on building
• You’re uncomfortable getting into production-level detail when the situation calls for it
• You expect an established engineering org with playbooks, processes, and a support structure already in place
• You’d rather delegate technical depth than engage directly
• Your experience is solely in product companies and you’re not interested in building for clients

Considerations

Education: Bachelor’s degree or equivalent experience; advanced degrees are a plus but not required

Ethics: Commitment to responsible AI practices — transparency, human oversight, privacy

Travel: Periodic (10–20%) for client work, team offsites, and events

Location: Remote-friendly; U.S. or Canada, with preference for EST timezone alignment

Why Join Human Agency

We’re profitable, growing, and building AI systems that run in production for billion-dollar companies. The team is small, the clients are real, and the work matters.

The work is real and the opportunity is massive. We’re building a company — the systems, the team, the delivery model, the culture — and we need someone to own the technical side of that build.

If you’re the kind of person who’d rather build the engine than describe the engine, we want to talk.

Equal Opportunity Commitment

Human Agency is an Equal Opportunity Employer. We value diverse perspectives and are committed to building inclusive, high-performing teams where everyone can do their best work.