Director of Legal @ Malbek | Legal Tech Author and Commentator | Fastcase 50 2022 Honoree | Legal Tech Startup Advisor and Investor

I help legal professionals, legal teams, and technology organizations make sense of legal technology so they can work smarter, deliver stronger outcomes, and lead with confidence in a field that is often noisy, fragmented, and misunderstood.

As General Counsel of Malbek and a long-time educator, author, and advocate, I sit at the intersection of law, technology, and learning. My work centers on translation. I take complex, fast-moving technologies and turn them into clear concepts, practical strategies, and informed decisions that legal professionals can actually use. Whether guiding teams through digital transformation or shaping how legal products are built and adopted, my focus is always on clarity over hype.

Teaching is core to how I operate. I regularly speak to diverse audiences, from military organizations to law firms and in-house legal departments, as well as large professional groups, on AI’s impact on legal work and the responsible, effective use of technology. Across these settings, my goal is the same: to help people understand not just what tools do, but how they change legal work, roles, and judgment.

That same educational mission runs through my writing and publishing. I am the author of The Legal Tech Ecosystem, a foundational guide to understanding the industry and its players, a co-author of CLM for Dummies, and the editor of the Handbook of Legal Tech. I also write regularly, serve as a columnist for Today’s General Counsel, and contribute through podcasts, webinars, and industry forums. Each platform is another way to make legal tech more accessible, grounded, and actionable.

Across every role, my aim is to equip people with the knowledge and confidence to engage with innovation thoughtfully and critically. If you are trying to cut through the legal tech noise, educate your team, modernize how your legal function operates, or build tools that truly serve legal professionals, I help move you from uncertainty to understanding and from learning to execution.

Let’s build what comes next.

Colin Levy

You can't negotiate AI contract provisions if you don't understand how the technology actually works.

The guide walks through it in the context of AI-specific contractual clauses:

What to flag, redlining suggestions, and negotiation suggestions.

Let me know what you think!

I'm Colin S. Levy, General Counsel at Malbek and author of The Legal Tech Ecosystem.

#legaltech #contracts #law #business #learning

Colin S. Levy

General Counsel at Malbek | Author of The Legal Tech Ecosystem | I Help Legal Teams and Tech Companies Navigate AI, Legal Tech, and Digital Enablement

AI Clauses Guide

Every time a lawyer asks an AI tool for case support, the tool delivers an answer with complete confidence. 

It formats the citation correctly. It names plausible parties. It describes a holding that tracks the legal issue perfectly. And sometimes, the case does not exist.

The challenge is not the fabricated citation you can catch with a quick database search. 

It is the real case with a subtly misrepresented holding, or the accurate legal principle supported by an invented authority. 

I wrote a guide that breaks this problem apart: 

-What hallucinations are at a technical level.

-Why the architecture of large language models makes them structural rather than fixable. 

-The categories of fabrication that show up in legal work

-How to build verification workflows that account for each one.

AI models are powerful. The outputs still require a lawyer's judgment.

I'm Colin S. Levy, General Counsel at Malbek and author of The Legal Tech Ecosystem.

#legaltech #contracts #law #business #learning

Managing AI Hallucinations Guide

Most legal teams do evaluate AI vendors before signing. The problem is often the evaluation isn't thorough enough.

I wrote a guide that covers the parts of vendor evaluation that standard processes tend to skip: 

Whether the company behind the tool will survive the next funding cycle, what "99% accuracy" actually measures (and what it hides), how to tell if a SOC 2 report is doing real work or just checking a box, and what your regulatory exposure looks like.

It pairs with my earlier guide on contracting with AI vendors. 

That one focuses on the contract. This one focuses on whether you should be entering into one at all.

I’m Colin, General Counsel at Malbek, and author of The Legal Tech Ecosystem. 

#legaltech #innovation #law #business #learning

AI Vendor Due Diligence Guide

Dynamic and award winning legal executive, tech leader, and change maker on a mission to humanize AI and technology. ~20 years of legal experience working with technology companies specializing in the intersection of law, AI / innovation, and product, and a talent for simplifying the complex, storytelling, and building relationships and community.  

Proven track record of:
- Growing top line revenue and brand awareness, improving conversion rates, and building pipeline 
- Recruiting, coaching, and managing high performing teams 
- Executing M&A transactions / integrations and financings 
- Managing governance, scaling operations, compliance, product counseling, employment, metrics / OKRs, and contract negotiations 
- Building community with practical trainings / content and authenticity

Recognitions (proudly not paid for): 
- 2024 Women, Influence, & Power in Law (Corporate Counsel) - Innovative Leadership
- 2024 WorldCC Foundation Inspiring Women in Commerce and Contracting 
- 2023 Washington State Bar Association Apex Award for Legal Innovation 
- 2021 Women, Influence & Power in Law (Corporate Counsel) - Thought Leadership - In-House Honoree
- 2020 Law.com/Corporate Counsel Magazine “Startup GC of the Year”
- 2019 The Business Journals’ Top 100 Legal Influencers
- 2019 National Asian Pacific American Bar Association Best Under 40
- 2018 Puget Sound Business Journal 40 under 40

* Views expressed are my own and not my employer. No legal advice provided or attorney-client relationship created. Consult with an attorney in your jurisdiction for advice on your particular issue. 

Jessica Nguyen

Bittersweet news: I’ll be entering a new season in my career but will remain the head of Contract Nerds 📝 🤓. After an incredible journey at Docusign, it's time for my next move. Stay tuned next Monday for an exciting new role announcement. Yes, I like to create FOMO. It’s my style. 

In all seriousness, I’m grateful for my time with the Docusign legal team. Working under the leadership of Jim Shaughnessy has been a privilege. He reminds me that careers are long and roles are shorter. We will have many roles over our career. An ally, mentor, friend, and so much more - thank you Jim for all you do for Docusign, the legal team, and the greater good. 

But this isn't goodbye goodbye. As I continue leading Contract Nerds my mission remains the same—build community and make contracts accessible, practical, and fun for everyone. 

To my Docusign colleagues: Thank you for everything. I’m looking forward to seeing all the great things you’ll achieve and will continue to ask you to contribute to the Contract Nerds community (I can no longer send you slacks but I will send you emails or LinkedIn messages). You can't hide from this nerd.

OK do you have FOMO? Can you give yourself FOMO? Goosebumps. 😉

Chief Strategy & Legal Officer @ Sandstone | Head of Contract Nerds 📝🤓 | Board Member

I speak with many legal tech founders. I’m usually skeptical in these conversations and think “please don’t be another CLM.” Well, as soon as I saw this product and met the team, I knew this could be the product to change the legal industry and I’d regret not joining. Living with no regrets is a life mantra because life is short and we should do things we love to do. 

🥁 Excited to announce I'm joining Sandstone as President, Chief Strategy and Legal Officer!

I was intentional about my next move. My requirements were:
✔️Build something transformative that’s better than the status quo. Not another contract redlining tool or something with little defensibility against major AI platforms.
✔️Swing big to help build THE comprehensive system for the next-generation legal department.
✔️Partner with people who share the same values, level of customer obsession, and performance standards. (This is often where teams / companies fall apart.)

Sandstone met all these requirements. Nick Fleisher, Jarryd Strydom, and team are building a platform that will change how legal teams operate for the better and is exactly what I wish I had (as Sandstone's CLO, I'm thrilled for a free license and top notch support—yippee!). While a lot of legal tech has emerged, most force you to change the way you or the business works and are still fragmented solutions that create more context-switching and app-shifting — not less.

Enter Sandstone. We're creating a centralized platform that understands how legal teams work, connects all the dots, and leverages AI to amplify legal expertise. We're calling it the "Legal Control Tower" that provides legal teams with the context, automation, and intelligence they need without asking the rest of the business to change the way they work or learn new tools. (If they use Slack, they stay in Slack). That’s right—No. Change. Management. 3 magic words in legal ops.

In my role, I’ll be guiding product development to ensure we're solving real problems for real legal users (my motto: “if Jess can figure out how to use it, anyone can figure it out”), managing legal ops so I never lose touch with customer pain, leading go-to-market strategy, and fostering a community of in-house legal professionals who will shape the future of our profession (join me!).

If you’re in-house and frustrated with today’s tools due to meh integrations, difficult implementations, or change management issues, let's talk. I'd love to hear what you wish existed.

Cheers to building the next-gen legal department. Let's go. 🚀

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Who’s an attorney that got to help design a stuffie my kids called a contract Jellycat? 🙋🏻‍♀️ 

For a chance to win a stuffed Clausey, join us this Thursday, February 26th for a free CLE accredited Contract Nerds 📝 🤓 webinar where we unpack “Data Security Terms: Essential Clauses in Vendor Agreements”, featuring:

✅ Cristin Flynn Goodwin, Managing Partner, Advanced Cyber Law
✅ Charles Post, Attorney and EVP, Cimplifi  

And hosted by yours truly. We’ll provide all registrants a handy data security terms checklist, deck, and the recording so register even if you can’t make it. * Note only live attendees eligible for CLE. 

REGISTER HERE >> https://lnkd.in/g7cgFdDm

Thank you sponsor and valued Docusign partner Cimplifi for making it possible to offer this CLE-accredited webinar to you for free!

If I knew then (back at my first GC role at Payscale) what I know now, I’d be a better GC and leader. Fact is being a great lawyer is one thing but leading the legal function for a company is an entirely different job. Really different and the easy part is legal work. 

That’s why I’m so excited that Ready Set GC  is coming to Seattle/ the Pacific Northwest on April 9th. This isn't just another networking event. It’s a space for women in their first GC/Head of Legal roles to get:

✔️ Candid, practical advice (no fluff).
✔️ Community support to navigate the challenges that "just being a good lawyer" didn't prepare us for.
✔️ Zero-cost access thanks to our partners at Perkins Coie.

Also rumor is I’ll be moderating a panel with C-Suite leaders (COO and CPO) who partner closely with GCs. Okay it’s not a rumor — I am! I am. Wooo. 🥳 Forgot to add if I can wrangle enough GC pals, dinner is on me after the event (not too expensive please as I’m paying for daycare). You don’t want to know how much daycare costs. 

Want to join us? Register here >> https://lnkd.in/g8w9gQPS

Join me and leaders like Deborah Solmor, Brianna Humphreville, Jen White, Natalie Kim, Meg McClellan and more!

Wowza—over 900 of you joined us live on today's Contract Nerds 📝 🤓 webinar to nerd out on data security terms! For my fellow practitioners: stop skimming the definitions. In vendor agreements, "Customer Data" isn't just a label—it’s the anchor for every obligation the vendor has to you. If you don't define it broadly, you're essentially building a house with a cardboard back door (if you know, you know when it comes to this analogy). 

Here are 3 things your "Customer Data" definition should cover:
✅ Beyond Just Data "Provided" by Customer: It’s not just the data you hand over. Consider including all data generated, collected, or processed by the vendor on your behalf.
✅ The AI Factor: In an "AI on everything" world, you need to explicitly include derived data and model outputs. If they build it using your data, you should have a say in how it’s protected.
✅ Metadata / Logs: Don't let vendors argue that operational and usage data falls outside the scope. Your own security program likely treats this as sensitive—your vendor's contract should too.

Negotiating for a broader "Customer Data" definition isn't about being difficult; it's about alignment on when the vendor's data security obligations (e.g., incident notice and liability obligations) are triggered. Note: it really helps to have leverage. Like, really helps. If you don't, control the risk by your usage/data shared and get good cyber liability coverage. 

Thanks again to our speakers Cristin Flynn Goodwin and Charles Post, and to valued Docusign partner Cimplifi for making this event possible.

Years before legal tech companies were cool enough to sign brand deals with actors like Gabriel Macht (aka Harvey Specter - I’ll confess I also enjoy Because I Said So and not just Suits), a poor kid with uneducated immigrant parents won a Washington State Bar Association Apex Legal Innovation Award for her vision of tech fundamentally changing the way lawyers do their work. It’s happening and the push for legal innovation is louder than ever. 

Speaking of Apex Awards, nominations are due this Friday, February 27. If you know a Washington attorney who is deserving please nominate them. There’s a broad range of categories for service, diversity, pro bono and more. Link to the nomination form in a comment. ⬇️

Special thanks to my friends Catherine Romero and Gaurav Oberoi for speaking on this video. I’d like to think we made legal innovation cool before it was cool. 😎 

Video here:  https://lnkd.in/gQhFtTTD

Rest in peace Diane Keaton and mom and dad.

Deputy General Counsel @ Docusign | Head of Contract Nerds 📝🤓 & Host of the “In-House” podcast 🎙️ | Board Member

Open video: 2023 APEX Awards, Jessica Nguyen on youtu.be

The best General Counsels (actually any business exec IMO regardless of function) go deep to learn the customer experience, industry, and customer experience (not a typo). And you can do this even if you work in B2B. Great to chat with Corporate Counsel / Law.com about how I've lived this in my B2B roles (which is less clear how to do so than a consumer role). 

Here are some examples of some things I've done: 
✅ Docusign: The Contract Nerds 📝 🤓 community is not a random acquisition -- it's an important channel for the business to learn what matters to a core product user and why - the community members live the agreement pain and want solutions to solve it (they also buy agreement tech). I also paid for a consumer e-sign account to walk through the UX and you'll often see me on LinkedIn replying to folks who have feedback. 
✅ Lexion: Beyond testing features to ensure it was usable by me (so usable by any lawyer), I did demos, wrote customer support content, and more! Everyone should be able to do a demo and answer a support ticket. 
✅ Payscale: Learned how compensation surveys were built and why so that when opposing counsel pushed back on data sharing language in the contract I could explain why it's industry norm, already done with other compensation surveys (existing risk), and also enabled pay equity compliance. 
✅ Microsoft: Grounded my GDPR compliance guidance on the customer experience and walked through the competitor experience and why my recommendation was more user friendly and introduced less friction. 

But don't take my word for it - hear insights from other legal leaders from other industries about why living in the trenches matters, including from Jason Winmill, Managing Partner at Argopoint. 

Are you a customer experience focused and industry savvy counsel? Add your thoughts below in a comment. ⬇️ 

Article here:

Open article: From Barista Aprons to Factory Floors: Why Top GCs Savor Time in the Trenches | Law.com by law.com

An image related to From Barista Aprons to Factory Floors: Why Top GCs Savor Time in the Trenches

From Barista Aprons to Factory Floors: Why Top GCs Savor Time in the Trenches | Law.com

Join us for a free CLE tomorrow. Even if you can’t attend, register to get a copy of the presentation, recording, and data security terms checklist. If you can make it, you know it may be the most fun legal webinar because the community is so engaged in the chat. Thank you Contract Nerds 📝 🤓!

And thank you to valued Docusign partner Cimplifi for making this event possible!

Award Winning In-House Counsel + Legal Ops Leader, Franklin Templeton ⚖️ | Founder, Contract Nerds 📝 🤓 | Author, Contract Redlining Etiquette 📕

As a tech transactions/commercial in-house attorney, there are certain contracts that I refer to as my "bread and butter", such as NDAs, MSAs, etc. 

But every couple of years, we get a new "jam"! First it was SaaS agreements instead of software licenses, then it was the GDPR-required DPA. Most recently, its AI Addendums.

As of a few years ago, Data Security Addendums (DSAs) became my new favorite jam! The importance of security terms in commercial agreements cannot be underscored. Almost every deal transaction we enter into has some level of security risk. Yet many agreements do not appropriately address the risks.

In-house counsel should be savvy enough that we can draft, review, and negotiate standard security terms and requirements. When things get complicated, I love partnering with my security term to work through the issues and come up with creative, practical solutions that work for both sides. But if we had to defer to security teams for every single security term, the bottleneck would develop very quickly and deals would stall.

In our upcoming Contract Nerds 📝 🤓 webinar on February 26th at 9am PST, we are going to dive into the topic of Data Security Terms: Essential Clauses in Vendor Agreements with Cristin Flynn Goodwin, Charles Post, and Jessica Nguyen. What's great is that the speakers will cover both the technical and the legal side, giving attendees a comprehensive overview of this topic.

All registrants will receive the following for free: webinar recording, presentation deck, and bonus DSA checklist. 

Attend live for CLE credit and a chance to win some of our awesome prizes!

REGISTER HERE: https://lnkd.in/dEmbdt3D

#datasecurity #securityterms #inhousecounsel #legalcounsel

A fun poll as we head to next week's Contract Nerds 📝 🤓 free CLE accredited webinar on Data Security Terms: Essential Clauses in Vendor Agreements featuring Cristin Flynn Goodwin (Managing Partner, Advanced Cyber Law) and Charles Post (Attorney and EVP at Cimplifi).   

If you haven't registered, I recommend registering even if you can't make it to get a copy of the webinar recording, the free checklist, and the presentation. CLE only available for live attendees. 

Register here >> https://lnkd.in/g7cgFdDm

I spend the most time negotiating this security clause

The author can see how you vote. Learn more

🥾 A hiking analogy to recap an AI addendum webinar? Yes, it's a way to show a human (me) wrote this vs. much more clever AI. Read my latest Contract Nerds 📝 🤓 article that recaps the AI addendum webinar featuring Laura Belmont and Matthew Kohel  and I share my 3 takeaways from the event. 

But more important than these takeaways is the fact that 75% of webinar attendees are still working on an AI addendum template. Yes, 75%! So even better than the article itself, there’s a link in it to an AI Addendum toolkit to help you get started or refine your draft. It includes: 

✅ Access the full 75-minute webinar recording
✅ Detailed presentation deck
✅ 6-page sample AI Addendum template
✅ Free bonus materials about AI contracting

Thanks again to the wonderful speakers and very engaged audience who make these events possible and the community thrive! 

Link to the article with the toolkit here >> https://lnkd.in/eEH9xiFr 

Ok, I confess. I’m not much of a hiker even though I live in Washington but I do love shopping for hiking gear at REI. That sort of counts.

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