Olga V. Mack

I design and measure legal and decision systems that govern how people allocate power, manage risk, and resolve conflict under uncertainty.

I am a legal technologist, CEO, and former General Counsel working at the intersection of law, technology, and organizational decision-making. I have founded and scaled multiple legal technology companies, including a legal tech startup acquired by LexisNexis, and I advise enterprises on risk, governance, and legal system design.

My work focuses on translating legal complexity into measurable, operational systems. This includes developing benchmarks for contract friction and trust, designing scalable legal workflows, and building tools that support durable decision-making across enterprise contracting, product law, litigation operations, and dispute resolution. Much of this work involves modeling how decisions are made under uncertainty and aligning responsibility, incentives, and control.

I have authored and edited multiple books and publications on legal innovation, technology, and governance, and I have delivered six TEDx talks on the future of law, AI, and human-centered legal systems. My work is frequently cited in discussions of legal innovation, AI governance, and the modernization of legal systems.

Previously, I served as a General Counsel, guided companies through IPOs and acquisitions, prosecuted cases as a San Francisco Deputy District Attorney, taught at Berkeley Law, conducted research at Stanford Law, and received multiple industry and professional honors.

I was born in Ukraine and immigrated to the United States as a teenager. I believe law should function as essential infrastructure: reliable, transparent, and accessible, particularly in moments of uncertainty and conflict.


Vice President & CEO of CounselLink CLM (formerly Parley Pro)

It was truly an honor for me to rejoin the LexisNexis family when they acquired Parley Pro.

As I continue my journey, my top priority lies in seamlessly integrating Parley Pro into LexisNexis CounselLink. This endeavor ensures that our valued users can fully benefit from the combined strengths and capabilities of both platforms.

I am passionate about disruptive technologies, including AI/ML, Web3, and data-driven solutions. Through embracing these innovations, I aim to foster a culture of service and drive forward-thinking approaches that push the boundaries of the legal industry.

My true calling lies in building the future of law, where digital transformation plays a central role. By empowering lawyers to become even stronger, more resilient, and more inclusive through embracing the digital realm, I believe we can create a legal landscape that truly makes a difference. It is my unwavering commitment to these passions that drives me forward each day.

Olga Mack

I’m an attorney and innovation leader focused on building the future of legal practice.

At Gunderson Dettmer, I was the first hire on our employment innovation team and helped build the practice from the ground up. Today, I head Employment Law Practice Innovation, where we’ve reimagined how our group works - redesigning workflows, streamlining delivery, and deploying AI-driven tools that make complex legal work faster, smarter, and more practical for startups, VCs, and their founders.

My approach is simple: reimagine how things could work better, then build the systems to make it happen. That philosophy has led to automated SMART Requests that give clients 24/7 access to our team, automated document solutions for key agreements like offer letters and PIIAs, and a suite of tools that streamline even the most complex workflows.

TL;DR: I am known for GETTING IT DONE. ✅

I love a complex challenge and thrive at thinking outside of the box to solve it - whether it’s advising startups on responsibly integrating AI into their hiring processes or helping established companies rethink workforce structures in the age of automation. 

I was among the first lawyers to publish thought leadership on generative AI. My 2024 Berkeley Business Law Journal article, "Why Lawyers Must Responsibly Embrace Generative AI," has been cited by federal judges, the New York State Bar Association's 2024 AI Task Force Report, the Washington State Bar Association's Board of Governors Report, the Sedona Conference Journal, Bloomberg Law, dozens of legal scholars and law reviews, and incorporated into law school curricula and ethics guidance nationwide. I'm a frequent speaker and published author on responsible AI, legal tech strategy, and the future of work.

I'm also the founder of Stephanie's Weekly AI Bites, which I started writing because I saw the same recycled AI headlines, but no actual practical guidance from those in the trenches. 

Over 3,000 (!!) subscribers -  founders, lawyers, GCs, leaders, and technologists follow along for 
useful guidance, not more headlines about how AI will either save or destroy everything. Plus, sometimes I'm funny. 😉

I'm always interested in connecting with others who share a passion for law and technology. If you're one of them, I'd love to hear from you!

🔗 Subscribe to Weekly AI Bites: https://www.linkedin.com/newsletters/7237800523259604993/?displayConfirmation=true.

Stephanie Goutos

Okay, the volume of DMs on this has officially exceeded my ability to respond individually 😅

So here’s the answer:
Yes, the prompt library is real.
Yes, it’s actually worth the hype (IMO). 

TL;DR: It’s a Google Sheet with 500+ prompts (and counting 📈) that I’ve personally tested and organized by category - operations, business development, knowledge management, HR, marketing, content creation, data analytics, and more. 

I built it over a span of a few months last year because I was tired of the “10 prompts that will change your life” posts…and spoiler alert: my life did not change 🙃

I’m sharing a few screenshots with examples, plus some feedback I’ve received:

“The spreadsheet is the perfect mixture of detail and simplicity. This is exactly where it needs to be to address various levels of technical expertise. I would be confident providing it to our younger staff as well as our most senior attorneys to demonstrate the power of AI… a powerful starting point to provide the team a great resource.”

I'm being thoughtful about who gets access and how it's used. This isn't a free resource - the time, testing, and iteration that went into it were real. If you're genuinely interested, drop a comment and I'll send you the details.

Thank you to everyone who’s shared feedback, comments, and suggestions so far,  I truly appreciate it! #AIinpractice #FutureofWork #Buildinginpublic

Some people go out on Saturday nights.

Sara Miro and I open our laptops and whisper, “this will only take 20 minutes.” 🌙💻 (Famous last words....)

Narrator: it did not.

Welcome to Saturday Night Vibes: Steph & Sara Edition.

The best part?

Zero pressure to be perfect. Just momentum, a lot of learning, and more than a few laughs along the way.

This isn’t productivity, and it’s definitely not polished, production-ready, or security-hardened. We know. That’s not the point. The point is staying experimental: testing ideas early, challenging assumptions, breaking things where the stakes are low, and learning fast.

And honestly? More women need to be in this phase of AI. Not waiting for permission. Not waiting to be “technical enough.” Just experimenting, building intuition, and getting hands-on because that’s where real confidence and fluency actually come from.

This is what real upskilling looks like: building reps, learning in public, breaking things on purpose, and getting 1% better every weekend.

This week’s build session was powered by:
 ☕ caffeine
 🧠 curiosity
 ❓ “how hard could this be?” (lol)

Featuring:
 Sara Miro as The Voice of Reason
 Me as "But What If We Try This Quick Instead"

Swipe the screenshots for some fun examples of what we came up with ⬇️. 

You’ll also spot a few other weekend sprint projects I've built for fun - compliance tools, content trend dashboards, and other “this might actually be useful” builds. All designed for people actually in the trenches doing the work.

Now your turn:

What have you built lately? Side project, weekend experiment, half-finished idea that taught you something - drop it in the comments. Jamie Tso we know you have something to share!! 😉 

And yes… if you’d like join Saturday Night Vibe Coding live on Zoom, say so. This could become a thing.

Happy vibing. ✨

#SNVB #SaturdayNightVibeCoding #VibeCoding #BuildInPublic #LegalTech #AIInPractice #FutureOfWork

“Yeahhh... I’m gonna need you to read this week’s AI Bites.”

In this week’s newsletter: 

🔥 Reid Hoffman is addicted to coding agents (same). And drops some fire predictions. 
🧠 AI slop is officially the Word of the Year. Your inbox knows why.
 🎓 Purdue made AI a graduation requirement. Somewhere, a Boomer just screamed into a fax machine. 
📚 Salesforce dropped an AI playbook. OpenAI launched ChatGPT Health. The bots are busy.
🤖 Your HR policy doc is still confidently wrong. Love that for legal.

Read it before your next meeting gets auto-summarized. Have a great weekend! #AI #FutureOfWork #LegalTech #WorkplaceAI #ClaudeCode #EmploymentLaw #WeeklyAIBites

View newsletter: Stephanie's Weekly AI Bites

TGIF & happy first full workweek of 2026! ☕️🤖 If you were hoping for a gentle ramp into the new year… the AI gods said absolutely not. Anyone else's 

Open article: Stephanie's Weekly AI Bites: January 9, 2026  by Stephanie Goutos • 4 min read

Stephanie's Weekly AI Bites: January 9, 2026

🚨 Gates. Musk. Goldman. Anthropic. All dropped AI + jobs takes this week.....
and they’re weirdly aligned.

This week’s AI BITES are hot off the press. 🔥

➡️ Gates is floating shorter workweeks (we’ll take it).
💥 Musk says AI can already replace half of white-collar jobs.
🐴 Goldman wonders if humans are "going the way of horses." (Rude, but okay.)
🤖 Anthropic shows enterprise AI is shifting from assist to automate.
🍏 Siri is getting a glow up. Apple finally tapped Google Gemini. The crossover episode we’ve been waiting for is here. 

#AI #FutureOfWork #LegalTech #WeeklyAIBites #Innovation #TGIF

Good Afternoon & TGIF!! This week felt like a cosmic group chat. Bill Gates, Elon Musk, Anthropic, and Goldman Sachs all dropped takes on AI and jobs,

Open article: Stephanie's Weekly AI Bites: January 16, 2026 by Stephanie Goutos • 4 min read

Stephanie's Weekly AI Bites: January 16, 2026

☄️ This week in AI: Claude published a Constitution.
Somewhere, James Madison just threw his quill. 

Also in Weekly AI Bites: 

Microsoft 365 went down.
Claude is writing Claude. (Read that again). 
AI hiring tools land in court. 
AI agents: cool in theory, messy in practice. 
Banks are already replacing roles.
Some judges want you to save your prompts. And more! 

#weeklyAIbites #futureofwork #AInews #employmentlaw #AIgovernance

Good Morning & Happy Friday!! Nothing says “we’re living in the future” like an enterprise‑wide Microsoft 365 outage. I'm definitely NOT saying Matt M

Open article: Stephanie's Weekly AI Bites: January 23, 2026 by Stephanie Goutos • 5 min read

Stephanie's Weekly AI Bites: January 23, 2026

We’re watching the future of work evolve in real time.

I spent part of the weekend testing Claude Cowork to see if it lived up to the hype.

Early verdict: powerful, a little chaotic, and genuinely useful. 

Here are my initial thoughts. More to come as this moves from experiment to workflow. 

#ClaudeCoWork #FutureofWork #AIinPractice

I spent some time this weekend seeing if Claude Cowork actually deserved the hype I’m seeing all over the internet. Here’s what I learned. So let’s st

Open article: Claude Cowork has entered the group chat. by Stephanie Goutos • 5 min read

Claude Cowork has entered the group chat.

🚀 The innovation economy moves fast, and the legal landscape is shifting just as quickly.

Gunderson Dettmer's Employment & Labor Group is hosting a series of in-person briefings to help founders, HR leaders, and in-house counsel prioritize the most critical issues for 2026. 

The sessions will be led by Natalie Pierce, Max Perlman, Mark Macchi, Chelsea Raiten, Jeff Salomon, Viviane Scott, and Jordan Simon. You won't want to miss this! #futureofwork #employmentlaw #innovationeconomy #workplacecompliance

Gunderson Dettmer’s 2026 Employment Law Update will feature in-person briefings at our offices in San Diego, Boston, Silicon Valley, and New York. These sessions are designed to help innovation economy founders, HR leaders, and in-house counsel identify and prioritize key employment law issues for the year ahead.

Led by attorneys Mark Macchi, Max Perlman, Natalie Pierce, Chelsea Raiten, Claudia Renert, Jeff Salomon, Viviane Scott, and Jordan Simon, these sessions will unpack major developments in AI regulation, pay transparency, noncompetes, state leave laws shaping the workplace, and more. Join us in person for live Q&A, networking, and practical guidance you can use immediately. 
 
Unable to attend in person? Access our webinar recording on February 4, organized into easy-to-navigate chapters so you can quickly find what matters most for your business. 

Register here: https://bit.ly/4jC6gLX

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