Deployment Strategist, Chicago | US$185K + equity

On site, with travel to client sites

"Make no little plans; they have no magic to stir men's blood." Daniel Burnham said that about Chicago more than a century ago, and the city took him at his word. Big shoulders, big buildings, big ideas. This role is in that spirit, just with a lot more Python running in the background.

The short version

A fast-growing, well-funded AI company is looking for a Deployment Strategist to join its Chicago team. They build custom, enterprise-grade AI systems for the industries that actually make and move things: manufacturing, logistics, heavy industry and other sectors where downtime is expensive and mistakes matter. Not chatbots for a landing page. Real systems running in plants, warehouses and operations centres.

The company is only a few years old, has raised serious money from top-tier Silicon Valley investors, and has assembled an engineering team from some of the best research institutions in the country. It is early, it is moving quickly, and it is very much a 0-to-1 environment.

What you will actually do

You will work in a small pod alongside Forward Deployed Engineers, and you are the strategic brain of that pod. The engineers build. You figure out what to build, for whom, and why it matters.

That means getting into a client's world fast. Walking a plant floor, sitting with a supply chain lead, mapping a messy process that has never been written down, and then working out where AI can remove real friction. You will scope and prioritise use cases, define requirements, design solutions, and translate all of it into something engineering can deliver in a realistic timeframe.

You will also own the client relationship. Boardrooms, executive sponsors, expansion conversations. You manage scope creep before it manages you and keep stakeholders aligned when the ground shifts, which it will.

Semi-technical work is part of the job. Data operations, basic analytics, an API-level understanding of how systems talk to each other. Nobody expects production code from you, but they do expect you to move without waiting for someone else to pull a dataset.

Who this suits

The client is honest about this: they need exceptionally strong problem solvers for this seat, more so than for almost any other role in the company.

Non-negotiables first. You need to be based in Chicago or willing to relocate, and willing to travel extensively to client sites. If that is a no, this is not the one.

The baseline they are calibrating against:

3+ years in management consulting, product management, or client-facing problem solving in traditional industries such as supply chain, manufacturing, distribution or defence
Consulting experience on operations or supply chain engagements, with McKinsey, Bain, BCG or a similar tier firm preferred
Client-facing work in real-world industries, not pure consumer tech
Proven ability to map a complex process and translate it into technical solution requirements
Clear evidence of elite intellectual performance. A degree from Stanford, MIT, an Ivy or equivalent counts, but so does a maths olympiad, competitive chess, a Fulbright, or top academic honours. They want a signal, not a particular logo

The things that will move you to the top of the pile:

Product management at an industrial or physical-world company (think robotics for infrastructure, not SaaS dashboards)
Startup or co-founder experience that shows you are comfortable with 0-to-1 ambiguity and owning things across functions
A quantitative major such as maths, engineering, economics or computer science
Semi-technical fluency: you understand APIs and can run basic data operations and analysis without waiting on anyone
Supply chain domain knowledge, especially MES, PLM, material planning or inventory management

And a few things that tend not to work: purely GTM, growth or commercial consulting with no operations exposure, productised deployment experience where the playbook was already written, or a preference for structured corporate environments. This is not that.

Why Chicago

Because it is where the work is. The client base sits squarely in the industrial Midwest, and the strategy team is built around being close to it. You will be based in Chicago and travel to client sites regularly. If you are currently elsewhere in the US and open to relocating, that is fine, and visa transfers (OPT, H1B) are on the table for the right person.

Also, deep dish, the lakefront, and a music scene that gave the world house music. There are worse places to build a career.

The offer

Base salary up to US$185K depending on experience, plus competitive equity in an early-stage company with serious upside. Full time, on site. The interview process is short and includes a process-mapping exercise, because they want to see how you think, not just hear about it. They want to move quickly.

One more quote, since we promised

Andrew Ng put it simply: "AI is the new electricity." The interesting part of that line is not the AI, it is the electricity. Electricity did not change the world when it was invented. It changed the world when somebody figured out how to wire it into a factory. That wiring job, done for AI, in industries that keep the lights on, is this role.

How to apply

Send your CV to Keiran at Big Wave Digital, or reach out directly on LinkedIn. Tell us in a couple of lines about the hardest process you ever had to untangle and what you did about it. That will tell us more than a cover letter ever could.

We are a boutique agency placing candidates across AI and tech in the US, and we read every application ourselves.