Remote Pilot Single Engine Jobs in Chicago, IL (NOW HIRING)

Location: Remote (US or Canada)

Type: US - Full-Time; Canada - Independent Contractor

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.

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.

This isn't a job posting with a defined box. It's an open door for someone exceptional who doesn't fit neatly into a single category. You're a builder who's proven you can ship, a generalist who moves between disciplines without losing depth, and an operator who sees AI as the engine for what comes next.

We're building ventures, serving clients at the highest level, and moving fast. We need people who can do more than execute a plan - people who can see around corners, build the plan, and then make it real. The Entrepreneur in Residence role exists because the right person is worth more than the right role. We bring you in, spend time understanding where you're most dangerous, and then aim you at the highest-leverage problem we can find.

You might end up leading a venture. You might architect a product that changes how clients operate. You might identify a gap nobody else saw and build the thing that fills it. What's certain is this: you'll be building from day one, and the shape of your work will be defined by what you're capable of, not what's written in a job description.

• Prototype and explore during an initial discovery period. You'll work closely with studio leadership to build, test, and validate ideas across potential venture opportunities. This is hands-on, not theoretical - you ship working prototypes and learn fast.
• Identify and commit to your highest-leverage opportunity. After the discovery period, you'll land on the role or venture where your skills create the most impact. This could be leading a new business, owning a major product initiative, or something we haven't conceived of yet.
• Build and ship relentlessly. Whether it's a client engagement, an internal tool, or a new venture, you're responsible for getting real work into the world. You're judged on outcomes, not activity.
• Contribute wherever the organization needs you. Before and after you land in your primary role, you'll work across the company - strategy sessions, client projects, product development, team building. Generalists don't wait to be assigned; they see what needs doing and do it.
• Raise the standard. You're here to make everyone around you better. That means honest feedback, rigorous thinking, and a refusal to accept work that's merely good enough.

• You've built things that shipped - startups, products, tools, systems, or movements. You have proof, not just stories.
• You're a generalist with depth. You can talk strategy with a CEO, build a prototype with engineers, and design an experience that users love. You move between disciplines without losing credibility in any of them.
• You're AI-native. You've built with LLMs, fine-tuned models, integrated AI tools into workflows, or shipped AI-powered products. You understand the technology and the business implications.
• You have a track record of operating in ambiguity. You've started things from scratch, pivoted when necessary, and delivered results without a roadmap.
• You can code, or you can design, or you can sell, or you can do all three. You have at least one hard skill at a professional level and enough range to be useful everywhere else.

• You're an entrepreneur, whether or not you've founded a company. You see opportunities, take ownership, and make things happen without waiting for permission.
• You're not looking for a job - you're looking for a launchpad. You want to build something meaningful, and you're willing to earn your way into that opportunity.
• You're intellectually honest and comfortable with feedback. You'd rather be wrong and learn than be right and stagnate.
• You're energized by high standards and great people. Mediocrity bores you. Working with exceptional teammates on hard problems excites you.
• You trust yourself. You've been in situations where nobody had the answer, and you figured it out.
• You can show us something you've built. If you can't attach proof to your application, don't apply.

• This is a full-time role and fully remote within the US or Canada.
• Compensation is competitive and commensurate with experience. We'll discuss specifics during the interview process.
• Occasional travel is required.
• You'll need to provide evidence of something you've built as part of your application. A GitHub repo, a live product, a case study, a portfolio - something that proves you ship. Applications without this will not be considered.

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.