Private
markets
AI advisory.
Built to work with your deal data, and not around it. Systems for private equity, family offices, and investment firms.
Gregory Villar · Ex-NASA JPL Systems Engineer
25+
3
148
14+
PE-backed portfolio companies
Executives coached 1:1
Roughly half my roster is private equity, family offices, and the portfolio companies they send me into.
9 PE · 3 VC ·
2 family offices
1:1 Sessions
Full operational diagnostic of your firm or portfolio company. Every automation opportunity mapped and ranked by ROI. If we don't identify at least $100K in savings, you don't pay.
AI Opportunity Audit
For Your Business
Private 1:1 coaching for GPs, managing directors, and operating partners. Eight sessions on your email, calendar, and deal workflow. Office Hours for Executive Assistants included. 12+ hours a week back for the decisions only you can make.
AI Executive Coaching
For the Executive
AI leadership for your firm, part time. I learn how your business runs, then map the highest-leverage places AI belongs in the tools and processes your business already uses. From there I train your team and build the systems that were mapped. Usually three to six months, scoped together, starting within a week.
Fractional AI Leadership
For the Firm
Results
Real firms. Real workflows. Specific outcomes.
Investor relations
Thousands of banker relationships consolidated into a systematic nurturing engine, personalized outreach drafted by AI.
This Managing Director needed to stay in front of 1,000+ banking contacts without manual upkeep. We built an investor relations system that surfaces who to contact, drafts the message, and logs the interaction, all inside the tools his firm already uses.
Financial model automation
Financial model reformatting dropped from 1–2 days per company to hours. PoC shipped in the first session.
This team was manually reformatting raw Excel output into a standardized investment model for every company they evaluated. We scoped and built the automation in a single working session.
Document workflow
Automated PDF monitoring across a multi-entity operation, sensitive art inventory and financial documents, with a fully data-private architecture.
This family office manager manages documents across multiple entities and jurisdictions with real data governance requirements. We designed a Dropbox monitoring and automation tool that keeps client data off third-party training sets entirely.
Services
AI Opportunity Audit
We map your company's operations end-to-end, identify where AI can replace manual work, and deliver an ROI calculator showing exactly how much time and revenue you can recover.
AI Foundations Seminar
A 60-minute team seminar that closes the gap between how your team uses AI today and what it's actually capable of. This leaves everyone with a shared prompting method and a blueprint for building your first AI systems together.
AI Executive Coaching
Weekly one-on-one sessions where we build AI skills tailored to how you work, so you and your team can move faster, handle more, and focus on what drives revenue.
Not just advice. Running systems.
Three tools built for real engagements, proven with real clients, ready to point at your business.
For PE, credit & VC
Deal Analyzer
Upload a CIM. It classifies deal type, extracts growth, margin, EBITDA add-backs, CapEx, and owner dependency, then scores it 1–10 with a kill/advance verdict, trained on your own firm's past memos.
For portfolio ops
Board Report Analyzer
Upload a board or portfolio report, get a summary of key points, flagged concerns, a turnaround plan for weak projects, and the top 5 questions to ask at the board table.
For any inbox
Voice File + Triage Starter
Reads your sent mail to build a tone profile, then drafts replies straight into Gmail drafts in your own voice, with a nightly refresh that keeps the voice file current.
Gregory Villar
About
I spent 14 years at NASA building systems precise enough to land rovers on Mars, Curiosity in 2012 and Perseverance in 2021. I apply the same methodology to your firm's operations: identify the constraint, engineer the fix, measure the result.
After JPL, I left to build companies. I've been on both sides of the table, operator and advisor. I started AI Window because most AI consulting is vague. What I do is specific: I map your actual workflows, find where time and money are leaking, and build the systems to close those gaps.
I keep my client roster small. This is a premium commitment on both sides.
What Our Clients Say
Managing Director
NYC Private Equity Firm
"The AI summaries are helping with first-pass deal review. My analysts used to have to read through all those books manually, this helps a lot. That was a real unlock for me."
Founder & CEO
Venture-backed Tech Company
"Gregory unblocked me. That's how I describe it to people, and that's my sell."
Investment Associate
Private Equity Firm
"In my mind, this is one of the best use cases I've seen. I would personally love to have an AI tool that could expedite the financial modeling process. I'm excited."
Fill out this quick form to get instant access to our growing library of AI tools and coaches, which include a Deal Analyzer, Document Analyzer, and AI personas modeled after Howard Marks and Richard Branson.
Free Resources
Ready to adopt AI?
Schedule a 30-minute conversation to get an honest look at where AI can move the needle for your firm.