AI & The Law

An Operator's Guide to AI Risk, Governance, & Contracts

A Collaboration between

Overview Syllabus Instructors FAQs Enroll today

Course overview

AI is reshaping how organizations operate and most leaders are navigating it without a map.

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This three-session live course equips Chiefs of Staff, Legal Ops professionals, and business operators with the strategic and legal fluency they need to guide their organizations confidently.

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By the end, you'll know the right questions to ask, the red flags to watch for, and how to become the most informed person in the room when AI decisions are on the table.

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This course is a collaboration between Operators (Chief of Staff Network, Legal Operators, BizOps Network) and Briefly (www.brieflynow.com).

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Key outcomes

Understand and apply core AI concepts to real business problems
Evaluate and implement AI solutions across teams with confidence
Navigate governance, ethical concerns, and change management
Develop and present a strategic AI implementation plan

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Course Details

Duration: 2 weeks
Format: 3 live sessions, with pre-readings, hands-on exercises, and one optional office hours
Certification: Digital certificate issued upon completion of all sessions and assignments

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Course Benefits:

Access to real-world tools and frameworks for implementing AI in your org
Ongoing community support via a private Whatsapp group
A final capstone project to showcase your learning and strategy

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Who Should Attend?

Chiefs of Staff & BizOps Leaders

Head of Business Operations

Future AI Consultants

Strategy & Innovation Leaders

Product & Growth Leaders

Chief Operating Officers

Business Transformation Leaders

AI-Driven Growth & Marketing Strategists

Tangible products to take away from these sessions were very useful. While great to have the “think big” conversations, it was also very nice to be able to walk away and come BACK to a real template or written framework to guide/reference.

Justin Shore

Chief of Staff, Wing.com

Syllabus & Schedule

Session 1: AI Risk vs. Reward: Building Your Organization's Adoption Strategy

Tuesday, May 19 at 12pm ET
Speaker: Damien Riehl, Clio
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Your CEO wants to move fast on AI. Your legal team wants to pump the brakes. Your job is somewhere in between. In this kickoff session, Damien Riehl, lawyer, engineer, and one of the most in-demand AI speakers in the legal world, cuts through the noise to give you a clear-eyed framework for thinking about AI adoption. From risk-tolerant tech startups to compliance-heavy healthcare systems, every organization faces the same fundamental tension. This session gives you language, scenarios, and strategies to navigate it — and to help your leadership team make smarter decisions faster.

You'll come away able to:

Session 2: AI Governance Crash Course: What the Law Actually Says Right Now

Thursday, May 21 at 12pm ET
‍Speaker: Shannon Yavorsky, Orrick

‍There's no single AI law - and that's exactly what makes this complicated. The EU AI Act is coming into force. Hundreds of state bills are actively being debated in the U.S., and in the meantime, existing laws like GDPR, CCPA, Title VII, the FTC Act, and huge numbers of state laws are already being applied to AI in ways most leaders don't realize. This session is a practitioner's guide to the current state of AI governance. We’ll cover what’s in force now, what's coming down the pipeline, and critically, what your organization probably needs to be doing right now that it isn't.

‍You'll come away able to:

Session 3: AI Contracting: Protecting Your Organization in Every Deal

Tuesday, May 26 at 12pm ET
Speaker: David Tollen, Tech Contracts Academy &
Sycamore Law Group

Most AI law is happening in contracts, not in legislatures. Whether you're buying AI tools, selling AI-powered products, or managing a vendor relationship that predates the AI era, the terms of your agreements matter more than ever. Data privacy clauses, indemnity provisions, and DPAs that seemed routine two years ago now carry entirely different weight. In this practical closing session, David Tollen, one of the country's leading experts on technology contracts, walks through what non-lawyers need to know to negotiate smarter, avoid costly mistakes, and work effectively alongside their legal and commercial teams.

You'll come away able to:

Bonus: Office Hours Session

Following the three core sessions, an optional open-format office hours will be available for registered attendees. No formal teaching, just open Q&A and peer conversation moderated by Adam Stofsky (Briefly) and the Sylva team. It will be a space to connect, share real situations, and get perspectives from others navigating the same challenges.

Meet your Instructors

Learn from operators on the frontlines of AI transformation.
Our instructors aren’t academics. They’re practicing Chiefs of Staff, technologists, and executive advisors who are actively deploying AI across high-growth startups, large enterprises, and mission-driven organizations.

Damien Riehl

Solutions Champion @ Clio

Damien Riehl is a lawyer, software engineer, and AI strategist who has spent over a decade building technology to make law more accessible. He contributes to product design and development at vLex (Fastcase), working with a dataset of over a billion legal documents across 100+ countries. A former litigator and cybersecurity practitioner, he chairs the Minnesota State Bar Association's AI Committee and serves on the board of Pro Bono Net, focusing on expanding legal services to underserved communities through technology.Previously, Scott served as Chief of Staff at Spring, Inc. (2013–2019), steering product strategy, fundraising (raising over $100M), investor and board relations, and scaling operations to 150 employees before the company was acquired.

Shannon Yavorsky

Partner @ Orrick, Herrington & Sutcliffe LLP

Shannon Yavorsky is Global Chair of Orrick's Cyber, Privacy & Data Innovation group and Co-Head of its AI practice. Qualified in California and England and Wales, she advises multinational companies on the full spectrum of U.S. and EU privacy, cybersecurity, and AI regulation, including the EU AI Act, EU Data Act, GDPR, CCPA, and HIPAA. Shannon helps global organizations navigate an increasingly complex regulatory landscape spanning data protection, digital markets, and emerging AI frameworks. Her clients are multinational companies across healthcare, technology, financial services, sports, retail, and automotive sectors.

David Tollen

Attorney & Founder @SYCAMORE LEGAL PC and Trainer & Founder @ Tech Contracts Academy®

David Tollen is the author of "The Tech Contracts Handbook," the American Bar Association's manual on IT contracts and a number-one bestseller from the ABA's IP Section. He is the founder of Tech Contracts Academy, offering live and on-demand training on software, AI, and cloud contracts, and of Sycamore Legal in San Francisco, where he drafts and negotiates technology and intellectual property agreements. He also serves as an expert witness in software contract litigation. Beyond his legal work, David is an award-winning author of educational fiction that uses fantasy to teach history and science.

Fellowship Benefits

Develop AI Strategy & Execution Skills

Hands-on AI Training

Expert-Led Sessions

High-Leverage Career Growth

Chief of AI Certification

Ready to Lead Your Organization’s AI Transformation?

Seats are limited to ensure high-quality interaction and personalized support. Join a cohort of forward-thinking Chiefs of Staff who are turning AI from buzzword into business advantage.

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Build strategy, drive adoption, and shape the future of work.

COHORT-BASED • 3 SESSIONS • Certification Issued

AI & The Law

$499

April 2 - April 23 2026

Last day to enroll: Mar 26

FAQs

Here are the most common questions we receive. If you have any further questions, the best thing to do is reach out to a member of our team!

What is the Chief of AI Fellowship?

The Chief of AI Fellowship is a 6-week applied learning program that equips Chiefs of Staff and operators with the tools, frameworks, and strategic mindset to lead AI adoption and implementation across their organizations.

Who is this program for?

This program is designed for Chiefs of Staff, BizOps leaders, and senior operators who want to turn AI from an abstract idea into practical workflows and business outcomes.

How much time should I expect to commit each week?

Expect to spend 2–3 hours per week across live sessions, pre-reading, assignments, and optional office hours. The more you engage, the more value you’ll take away.

What if I can’t attend a live session?

All sessions are recorded and made available to participants within 24 hours. You’ll need to view recordings and complete all assignments to qualify for certification.

Will I receive a certificate?

Yes! Participants who attend or view all sessions and complete the assignments will receive a Chief of AI Fellowship certificate, which can be added to LinkedIn and other professional profiles.

How is this program different from other CoS courses?

This is the only course focused specifically on helping Chiefs of Staff and operators apply AI in their work through practical workflows, strategic planning, and responsible implementation frameworks.

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