A Boutique Legal Technology Consultancy

Build Confidence in Your AI Strategy

Explore. Imagine. Execute.

What We Do

Applying AI & Building What's Next

01

Applying AI — Adoption Consulting

Law firms are leveraging AI to improve legal outcomes, reduce costs, and win new clients. Let us be your partner in crafting your AI vision and delivering on it. Partner with Cutterhead to gain confidence in the best path for your firm and your clients.

As your partner, Cutterhead will help you better grasp the current technologies available, from frontier models like OpenAI and Claude, to Legal AI Assistants like Harvey and Legora, to products like Relativity, Entegrata, NewCode, Orgaimi, Neo Stella and Justice Bid.

We understand that each law firm is unique. We have no incentives other than helping our clients discover and implement the technology answers that are best for their law firm.

02

Custom AI Solution — Design and Development

There has never been a better time for law firms to differentiate through custom software solutions. Cutterhead understands how to define and build tailor-made solutions at lightning speed and at a surprisingly low cost. Partner with Cutterhead to simplify your firm's operation, create compelling solutions, and demonstrate to your clients a leap forward in your services.

03

Relativity — Customizations

Relativity is the market's leading AI platform for data discovery. Relativity is powerful, complex, and extensible. Cutterhead can help you define and develop a Relativity experience tailor-made for your firm.

04

Test Data Generation

Realistic synthetic eDiscovery datasets — built from a detailed scenario bible, ready for any eDiscovery platform. Each dataset is a complete fictional eDiscovery matter, with the right mix of signal, noise, privilege, and red herrings to train reviewers, benchmark analytics, and realistically demonstrate software.

Learn more about synthetic data

About

A Message from the CEO

Illustrated portrait of Kit Mackie

Amid the AI news bombardment we experience most days, it's hard to miss that our world is rapidly changing. This can feel unsettling. If we move past this uncertainty, we can discover a world of vast opportunity. There has never been a more exciting time for technology, and specifically, legal technology. Cutterhead exists to help you discover this opportunity, and navigate to a brighter future.

I have spent over 20 years leading the development of products in the legal technology market. During this time, the most important lesson I've learned is that technology can be powerful; it can change the trajectory of a business and even an industry. Critically, this happens only when the teams managing the technology are wholly committed to serving the needs of their clients. This lesson is embedded in the founding of this business, and it will always be our north star, as we strive to foster the development and adoption of technology solutions.

At Cutterhead, we endeavor first to learn. We understand the legal technology landscape, and the processes required to manage AI and software development. We do not yet understand your business or practice, your history, your clients. If you are willing to share your desires, your pains, your needs, and dare we say, your dreams, we can help you discover possibilities that alter the trajectory of your business or practice.

Kit

Kit Mackie, Founder and CEO

About Me

I professionally came of age in the early 2000s, when the internet was in its infancy. I rode that wave of change as a seminal employee or founder at three successful businesses: Relativity, NexLP, and Lineal. I ran the product development of Relativity, from the 1.0 version through the 7.4 version, over a ten-year span. I was an early AI believer, as we founded NexLP in 2012 on the backbone of Dr. Dan Roth's life's work. Dr. Roth is a McCarthy award winner, presented each year to the world's top AI scientist. In my third endeavor, I conceived and led the development of Lineal's Amplify suite (gratitude to Jeanne Somma for many, many insights) which won numerous awards and continues to drive Lineal's marketing messages to this day.

Cutterhead is my fourth and final business. I hope to grow this business with my clients for many years to come.

I have always been an engineer and a technologist first. My passion is connecting the dots between technology, business and people. My best days are those where I work with clients and teams to discover solutions to complex problems. Through conversation and process, we can ease professional pain. We can deliver systems that allow you to delight your customers. And this has never been more true than it is today.

I am the father of four. I love to drum, golf, and ski. I am a proud Chicagoan and graduate of the University of Illinois School of Engineering. I L L!

Cutterhead — What's in the Name?

Kit's parents, uncles, cousins, and siblings all worked in the dredging business. For him, it was an early source of fascination in business and technology. He spent summers in college working on beaches and dredges.

A cutterhead dredge is a powerful marine vessel that uses a rotating mechanical cutter head to loosen hard soil, clay, or rock on a seabed — clearing the way so the water beneath can be put to new use. It seemed a fitting namesake for a business built to cut through complexity and clear a path forward.

Illustration of a cutterhead dredge: a vessel with a ladder arm extending to a rotating cutter head on the seabed
A cutterhead dredge: a rotating cutter loosens the seabed so the channel behind it can be put to new use.

Let's Talk

Ready to build confidence in your AI strategy?

Reach out and let's start the conversation about where technology can take your firm.