AIFractional Lawyer Contact
Transactional Counsel

Senior judgment, with AI tools and AI speed, without the drag of institutional overhead.

Actively engaged product and commercial counsel for venture-backed, AI-native startups.

Experience Cooley·Microsoft·Intel
Twelve years of AI legal experience (formerly machine learning)
01  /  About Counsel
Phil Tanaka, fractional general counsel
Phil Tanaka
Transactional Counsel

Experience leading adaptation at startups, large firms, and major tech platforms.

Inhouse development of accurate, custom, segregated AI systems for each client, with negligible expense.

Experience Selected
Firm
Focus
Cooley

Former leader of the Northwest technology-transactions practice. Deep experience in commercial contracting, licensing, and scaling technology businesses.

Microsoft

First outside counsel to the machine-learning and AI group, negotiating early arrangements on training data, outputs, and ownership before industry norms existed. Helped lead the open-source transition, Azure and enterprise commercialization, and decentralized identity.

Intel

Embedded, seconded counsel, combining operational business reality with legal analysis, and the interplay of inbound and outbound obligations.

International

Cross-border transactions in Japan (Nagashima Ohno) and Israel (Yigal Arnon), bridging different commercial cultures and approaches to risk.

02  /  The Shift The case

Knowledge is valuable, but what you pay for it depends on its scarcity.

AI makes legal knowledge not scarce and therefore not costly.

Judgment and the ability to automate workflows with systems of record are now what's most valuable.

What stays scarce Cost vs. value
AI ARRIVES Value of judgment Cost of legal knowledge Cost of legal execution

Deploying that judgment well still takes deep, developed skill. What is new is the greater speed and efficiency, as well as lower cost, that were never possible before. The same knowledge, delivered without the institution wrapped around it or holding it back.

The premise

If your company is AI-native, your legal counsel should be too.

03  /  Why Big Law is Broken The market

Big firms face the same trap as the web-design agencies of the 1990s. Most of what they do can now be done better, faster, and for less by someone using AI well.

When half to three quarters of a firm's work can be transformed by tools, a large institution slow-walks the change. People there are rewarded for not making mistakes, not for innovating. That is the opposite of how a founder operates, and it puts the firm's pace out of step with its clients.

A firm also sets policy across the whole institution, so its judgment defaults to the lowest common denominator, optimizing for broad safety rather than spotting the specific opening that turns into an advantage for you. AI cannot be used indiscriminately, but problem-solving moves much faster with a single client and specific facts at hand than under firm-wide policy. Agility is a feature, not a compromise.

04  /  What We Do Practice

Beyond the obvious, what startups need most is loyalty. Your transactional counsel must be embedded in your business and care about its success the way you do. AI efficiency enables greater productivity at lower cost, and frees up more strategic and personal attention for what matters most to you.

AI should dramatically change transactional practice, automating your differentiated contract flow, including NDAs, MSAs, and DPAs, along with any other commercial, privacy, security, regulatory, or related agreements.

05  /  Our Approach Method

An AI-native workflow, with senior judgment on everything.

Using systems that deploy accumulated judgment alongside the best generalized knowledge available, built around your business.

The workflow Senior review throughout
SENIOR JUDGMENT, OVERSIGHT AND AI ENABLEMENT Your system of record AI, applied accurately The work Prior transactions & your context Your team's first pass OPTIONAL
SENIOR JUDGMENT, OVERSIGHT AND AI ENABLEMENT
Your system
of record
Prior transactions
& your context
Your team's
first pass
OPTIONAL
AI, applied accurately
The work

Built around your system of record

We work inside your context: prior transactions, templates, and the way your business actually operates. The work is informed by what you have already done, not started from a blank page.

AI applied accurately, with oversight

We can start manually to get grounded. Wherever AI can do the work accurately, under senior review, we use it. Judgment sits on top of everything, and the real risks, accuracy, privilege, confidentiality, are managed deliberately.

Your team can take the first pass

If you want, your team can take the first pass on your own work, and I'll bring senior review on top. You decide how hands-on to be, and where that review is worth it.

§   Who It's For Selectivity

We don't take every client.

The fit

But if you're a venture-backed startup with corporate work like financings and M&A already handled, and you need product and commercial counsel that moves fast, brings AI into the legal work itself, and carries senior judgment, you're likely a great fit.

§   Contact Inquiries

If you're building something AI-native and need counsel that keeps up your momentum and adds to it, let us know what you're working on and how we might be able to help.

Or write directly
phil@philiptanakaps.com