Director, AI Transformation

Human Agency · Chicago · Remote

Posted 7/20/2026 · last confirmed live 8/26/2026

Location: Remote Type: Full-Time Employee for US Candidates; Independent Contractor for Canadian Applicants **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 create 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 Most AI consultants are good at one of two things: writing the strategy or doing the work. We need someone who refuses to separate the two. This role exists because our clients don't just need a roadmap - they need someone who will build the road, navigate the detours, and still show up to the steering committee with a clear-eyed point of view on where they're headed next. You'll lead AI transformation engagements end-to-end, from diagnosing what's broken and what's possible to rolling up your sleeves and building the thing alongside the client's team. That might mean designing an AI-enabled workflow on Monday, pressure-testing a product decision with a C-suite on Wednesday, and shipping a working prototype by Friday. The client doesn't see the seams. You own the outcome. This is the right role if you've spent years inside Big Four firms, strategy boutiques, or early-stage companies and found yourself frustrated by the gap between advice and execution. You know what good looks like, you've seen what happens when no one stays accountable for making it real, and you're done handing off decks to someone else's team. You want the whole thing - the strategy, the build, the proof. What You'll Own Client Engagement Leadership — Run AI transformation projects from discovery through delivery, serving as the primary client relationship owner and the person ultimately accountable for outcomes. Strategy and Execution, Both — Develop transformation roadmaps grounded in a client's actual constraints, then stay in the work long enough to see them implemented, not handed off. 0-to-1 Product Building — Identify high-value AI use cases, prototype solutions, and shepherd them from concept to something clients can actually use, often building hands-on alongside the client's internal team. Executive-Level Communication — Translate complex AI concepts, technical constraints, and strategic tradeoffs into crisp, confident communication for boards, C-suites, and frontline operators alike. Go-to-Market and Growth Support — Contribute to business development, help scope new engagements, and actively deepen relationships with existing clients as their needs evolve. AI Tool Deployment — Apply AI tools aggressively across your own workflow and your clients', not as a demo, but as a working standard for how fast and how well this work can get done. Internal Contribution — As a senior member of a flat, growing team, you'll help shape how Human Agency delivers, what we learn, and who we become. Who You Are Experience & Skills 5–8+ years of experience in management consulting, venture-backed startups, product strategy, or a combination, with direct ownership over outcomes, not just deliverables. Demonstrated track record of taking AI from concept to working reality in an organizational context — not just advising on AI strategy, but building or deploying something that worked. Fluency with the AI tooling landscape — foundation models, workflow automation, prompt engineering, and the judgment to know when to build versus buy versus recommend against. Proven ability to lead client relationships at the senior level, including navigating organizational politics, managing ambiguity, and keeping complex engagements on track without a safety net. Strong written and verbal communication — you can write a crisp executive brief, run a working session with a skeptical VP, and explain a technical architecture decision to a non-technical founder, often in the same day. Experience in 0-to-1 product building — you've shipped something, taken something from nothing to real, and you can speak concretely about how you did it. Bonus: Background in venture studios, high-growth AI or tech companies, or operator roles at the intersection of strategy and product. Mindset & Traits You're a builder first. Decks are useful; working things are better. You default toward making something real. You manage yourself completely. No one will check on your progress, remind you of a deadline, or coach you through a hard week. You are the accountability structure. You have no patience for the gap between strategy and execution and have spent your career closing it. You're curious about AI in a way that shows up in your actual work — you experiment, you break things, you have opinions formed by firsthand experience, not secondhand summaries. You can hold the big picture and the small detail simultaneously, and you know when to zoom in and when to zoom out without being told. You do what the work requires. Not what's in scope, not what's comfortable, not what's in your lane. Logistics Location: Remote-first; US and Canada eligible.  Travel: Occasional travel required for client engagements, company offsites, and key strategic meetings. Application Note: Attach proof of something you've built with AI — a product, a workflow, a tool, a result. If you don't have something to show, this is not the right role. 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.  

This role is published by Human Agency on greenhouse. SwiftFit is not the employer and does not accept applications.