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.

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Olga Mack

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