Chief of Staff - Chicago

Location: US 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 at 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

This is not a traditional chief of staff role. At Human Agency, the chief of staff is the prototype for every person we hire. You're someone who wants to be running a company — a dynamic C-suite leader — but you're choosing to ride shotgun alongside an executive because you know it's the fastest path to getting there. What makes us different is that we actually give you that shot. Today. Not in three years.

You are floor to ceiling. You will take out the trash, sweep the floors, and then walk into the board meeting and run it. Nothing is beneath you. There is no ceiling above you. You are a garbage disposal for problems — every food scrap, every random piece of metal gets thrown your way, and you figure out how to handle it without breaking.

What You'll Do

Rather than being hired for a predetermined set of tasks, you will be brought on to solve complex, evolving challenges. Success in this role requires self-direction, proactive value creation, and the ability to thrive without constant oversight. Over the coming year, your responsibilities will be tailored to both organizational needs and your individual strengths, potentially including:

• Leading AI transformation projects with clients
• Leading fundraising efforts for funds or clients
• Managing investment funds
• Managing CEOs at client organizations
• Driving sales initiatives at Human Agency
• Partnering closely with recruiting to help grow our team
• Serving as CEO of a venture studio company
• Managing client project delivery
• Driving value through data and analytics for clients
• Leading go-to-market initiatives for clients
• Own and solve ambiguous, high-stakes problems that don't fit neatly into any department
• Manage yourself entirely — no hand-holding, no coaching, no check-ins about how your day is going
• Move between strategic work (board prep, investor materials, business development) and ground-level execution (scheduling, research, client fires) without blinking
• Deploy AI tools daily to amplify your output — you are not doing the work of one person, you are doing the work of five
• Identify opportunities, inefficiencies, and threats before anyone asks you to

What We're Looking For

• A fundamentally good human. Table stakes.
• Mission-driven operator with deep commitment to Human Agency's values and vision
• No ego. No job description. You do whatever the job requires.
• Self-managing problem solver — the last thing a CEO or Founder wants is someone they have to manage
• AI-first mindset — you use AI as a force multiplier across everything you touch
  • Builder mentality — you've shipped something. Attach proof of something you've built with AI to either your application or cover letter.
• Generalist with range — you don't need to be an expert in any one thing, but you need to be dangerous across many things

Experience & Skills

• 5-7+ years in high-performing environments such as management consulting, venture capital/private equity, business development, or startup leadership positions
• Demonstrated success in taking ambiguous, complex initiatives and driving them to completion, you're the person who makes hard things happen
• Outstanding written and verbal communication; you can synthesize complex information into clear, actionable briefs for different audiences
• Bonus: Experience in high-growth startups, venture studios, or AI/tech companies

Considerations

• Education: Bachelor's degree or equivalent experience; top-tier programs and/or an advanced degree in a relevant field is a plus
• Ethics: Commitment to ethical practices and responsible business operations
• Travel: Occasional (10–25%) for company offsites, key events, and leadership meetings
• Location: Remote-friendly with preference for candidates in major tech hubs and strong preference for overlap with EST business hours

Equal Opportunity Commitment

Human Agency is an Equal Opportunity Employer. We value diverse backgrounds and strive to build an inclusive culture where everyone feels welcomed and empowered.