Based in Chicago, IL

We started this because most
AI projects fail — and we knew why.

Cass Ave Consulting was built by two people who kept seeing the same story: companies eager to adopt AI, burned by implementations nobody used, and unsure who to trust. We started this to do it differently.

The hardest part isn't
the technology.

We kept having the same conversation. A leader would tell us they knew AI was important — that their board was asking about it, their competitors were moving on it, and their team was ready to embrace it. But when it came to actually deciding where to start, what to invest in, and how to make sure it paid off? That's where things got murky.

The tools are more capable than ever. The real challenge is knowing which ones are worth it for your specific business — and how to introduce them in a way that genuinely changes how your team works, not just adds another platform to the stack.

We started Cass Ave Consulting to be the partner that answers those questions honestly. Not with a generic framework or a predetermined solution, but by actually understanding how your business runs — and building something that makes your people better at what they already do well.

01

The moment we kept seeing

Smart leaders, real pressure to act, and no clear answer on where AI would actually move the needle for them specifically. Generic advice was everywhere. Honest, business-specific guidance was not.

02

What we set out to build

A consulting firm that starts by understanding your business before recommending anything — and stays engaged until what we build is genuinely part of how your team works, not just handed over and invoiced.

Your best people already know your business. AI gives them the time and tools to do more of what only they can do.

We don't measure success in features shipped or tools deployed. We measure it in what your team can do after we leave that they couldn't do before — faster decisions, reclaimed time, sharper judgment. That's the standard every engagement is held to.

🎯

People before technology

We design for the humans who will use what we build — not for a demo, not for a deck. Adoption is the goal from day one.

🔍

Diagnosis before prescription

We audit before we recommend. We never arrive with a predetermined solution looking for a problem to attach it to.

🤝

Honest over impressive

If AI isn't the right answer for something, we'll tell you. That honesty is what earns the trust that makes the work actually land.

📐

Fit over one-size-all

A bootstrapped 15-person startup and a 400-person manufacturer need fundamentally different things. We scope and build accordingly.

We're not a typical
AI consultancy — and we mean that.

01

We don't call it done at delivery

Most consultants hand over a finished product and move on. We stay until your team is genuinely using it — and we build adoption into the project from the start, not as an afterthought.

02

We bring tech and operations together

Our team is built from both sides: deep technical capability and real operational experience running businesses. That combination is rare — and it's why our implementations actually hold up in practice.

03

We work at every stage and size

We don't have a minimum company size or a preferred client profile. We scope every engagement to fit where a business actually is — not where a standard retainer assumes they are.

04

We're honest when AI isn't the answer

Not every problem needs AI. Sometimes the right answer is a simpler process change, better tooling, or just cleaner data. We tell you that — even if it means a smaller engagement.

05

We build for your industry, not in general

Healthcare compliance, manufacturing workflows, financial reporting, retail operations — we work in the specifics of your world, not generic AI use cases that sound good in a pitch.

06

We understand your operating context

We work in the specifics of your world — the industries, the workflows, the pressures your team is actually under. When you work with us, you're working with people who get your context, not just your category.

Two founders.
One shared belief.

We built Cass Ave Consulting because between the two of us, we'd seen every way an AI implementation could go right — and every way it could go wrong. Both of us have led teams, managed complex projects, and watched technology either transform an organization or get quietly abandoned. The difference is where we each started: one of us from the technical architecture out, the other from the operational structure in. That combination is what makes the work actually land.

P Add your photo
Co-founder
President
Head of Engineering & AI Development

[President's bio goes here. Lead with leadership and people instincts first, then bring in technical depth as the asset he brings to that leadership. Suggested tone: "[Name] has spent his career leading teams and building the kind of technical systems that actually get used — which, in his experience, has everything to do with the people around them. His ability to bridge the human and technical sides of a project is what has driven his growth as a leader, a manager, and an engineer. He co-founded Cass Ave because he believed there was a better way to bring AI into organizations — one that starts with understanding how people work, not just what the technology can do."]

AI & ML development Team & project leadership Systems architecture People-first engineering
DIO Add your photo
Co-founder
Director of Intelligent Operations
Head of Strategy & Client Success

[Your bio goes here. Suggested 3–4 sentences covering: your operational or industry background, what you've led or built inside organizations, the moment you understood that AI adoption was a people problem not a technology problem, and what drives you about this work. Example tone: "I've spent my career inside organizations trying to make complex operations run better — and I've watched too many good technology investments fail because nobody thought carefully about the people on the other end. That's the problem Cass Ave exists to solve."]

Operations strategy Change management Client success Chicago, IL

If this resonates,
we'd love to meet you.

Book a free 30-minute discovery call. We'll ask about your business, share where we think AI could help, and be straight with you about whether we're the right fit. No pitch, no pressure.

Book your free discovery call

30 minutes · All company sizes welcome · We work with businesses nationwide