● Trevor James

Chicago

AI Builder & GTM Operator · Chicago

Trevor James

I build the financial case that closes enterprise deals, then build the AI that proves the value is real.

Production AI4 production systems in weekly use

Value engineeringAmLaw 200 ROI + pricing model

Partnerships19,000-agent distribution deal

See the work →Connect

Proof of workThings that exist because I made them

Every month, I take the ROI model and pricing case for a decision-intelligence product in front of Fulcrum executives and outside investors. I own the number they use to decide whether the build keeps moving.

Legaltech · Value engineering · Now

A stealth VC firm

I’m embedded as the firm’s AI builder. Four production systems are in weekly use: scoring across a 2,500+ company taxonomy, traction monitoring for 280+ companies, tear sheets grounded in 4,000+ partner meeting notes, and citation verification before a partner sees the output.

AI build · Confidential

I taught myself enough software development to build OPAL, a live strategic-analysis platform. It turns company data and unit economics into a first-pass business case for about $0.50 in inference per report.

Founder · AI build · Live

My Legal Academy

At My Legal Academy, product and sales were the same job. I helped launch an AI legal-transformation product to $45K MRR and rebuilt the sales operation as ARR grew 76%, from $680K to $1.2M, in the same 90 days.

Legaltech · Value + sales

I held two very different jobs at Zillow. In Homes, I led a six-person team processing roughly $145M in home-sale volume each month and kept the team producing through the iBuyer shutdown. In Rentals, I managed a $10M enterprise portfolio, built the value case for national REITs, and negotiated the multi-year agreements.

Enterprise · Executive buyer

Builder · Operator · Founder · Strategy · Tech

Trevor James

I believe in grit and growth, but mostly in adaptation.Start. Iterate. Measure. Track what happens. Make it better.

How I defend a number

A law firm was considering a $30K transformation program. I used its average retainer to show that four or five additional cases would pay for the program within a year, before counting any efficiency gains. Then I wrote the playbook for criminal defense, immigration, family law, estate planning, and personal injury.

The model worked because it started with a number the buyer already trusted.

The full story — My Legal Academy →

I like hard products, skeptical buyers, and numbers that have to survive scrutiny.

If we talk, ask me to open the model—or the code. I’d rather be tested than summarized.