Ari Kaplan recently spoke with Brian Powers, the co-founder and CEO of Markups.ai, a company that created an AI agent called Agent Marko to draft, revise and analyze contracts from clients’ inboxes with no new platform required, and Debbie Epstein Henry, the founder of DEH Consulting, Speaking, Writing and the chief strategic adviser to Markups.ai.
They discussed the advantages of using an AI agent in contract review, where startups can distinguish themselves in a crowded market, the misconceptions about AI that leaders need to address before they can achieve broad adoption, and the skills legal professionals should enhance to fuel their success.
Ari Kaplan: Tell us about your background and the genesis of Markups.ai.
Brian Powers: I started my career in investment banking at Moelis in New York, and like any good analyst, I had my fair share of NDAs. Then I founded a company called TemperPack, which makes sustainable materials to replace plastics like Styrofoam, and we grew it to over a hundred million in sales. We sold quite a bit of it to private equity firms led by Goldman Sachs a few years ago. Along the way, we were frequently challenged on our contracts. We had many large clients across different sectors, and we had lots of good solutions for storing contracts but nothing to assist with the actual negotiations. My co-founder at Markups.ai, Sam Shelley, began his AI career at Dataminr over a decade ago, then started Vault Health, which became one of the largest COVID testing telemedicine businesses. In 2023, we teamed up with the idea of using the latest AI technology that had recently emerged to help automate contract negotiations, aiming to do so without onboarding a new platform and making the process more customized and user-friendly.
Ari Kaplan: Tell us about your background and your role as chief strategic adviser for Markups.ai.
Debbie Epstein Henry: I call myself a recovering lawyer turned professional speaker, communication coach and entrepreneur. What’s more relevant to my background for today’s conversation is that I co-founded a company called Bliss Lawyers, which was a secondment firm. I ran that company with two other partner co-founders for nearly nine years, and then we were acquired by our biggest competitor, Axiom, in February 2020. So I was actually out of legal innovation for a while before joining Markups.ai as chief strategic adviser. For the company, I mainly speak to prospective clients daily as they evaluate different AI tools, which every company and firm is doing right now. I also advise Markups.ai on trends in the legal profession because our two co-founders aren’t lawyers and need to stay informed about what’s happening in the field. We discuss current trends and what clients expect from their outside service providers.
Brian Powers is the co-founder and CEO of Markups.ai, a company that created an AI agent called Agent Marko to draft, revise and analyze contracts from clients’ inboxes with no new platform required. Debbie Epstein Henry is the founder of DEH Consulting, Speaking, Writing and the chief strategic adviser to Markups.ai.
Ari Kaplan: Why did you design Markups.ai to work with an agent, rather than the more common approach to using AI to manage contracts?
Brian Powers: Some of it was what we believed was missing in the market, but there were also three major reasons that motivated us to create and use a product like this. First, we wanted something that was much easier to onboard. I still get shudders when I hear the word “platform”—that means my next year’s plans are disrupted, and it will be a long wait before we see any benefits. Second, I wanted something more intuitive to use, especially with AI, that is easy to operate but also really powerful. Our goal from the start was to create something so simple that even my two lawyer parents could use it. Third, we aimed for something far more customizable than most software platforms. Most platforms are designed to fit many different businesses doing similar things, but there was an opportunity to develop something that could handle highly tailored work. For the first time, AI-powered software could achieve this, with an agent doing the work. We develop a new version of our agent for each client, ensuring everything they do is uniquely customized.
Ari Kaplan: What is most important for legal tech startup founders to consider in the current market?
Debbie Epstein Henry: The primary consideration should be workflow. The main obstacle to AI adoption is when an AI tool doesn’t easily fit into a company’s existing workflow. That’s why our engineers at Markups.ai developed an email agent because email is the most natural and straightforward integration point. This isn’t just based on our experience; it’s backed by two recent studies, one by McKinsey and the other by MIT. Ultimately, it’s all about simplifying workflow and seamlessly integrating with existing company systems.
Ari Kaplan: What are the advantages of using an AI agent in contract review specifically?
Brian Powers: The two holy grails are one that saves time and also makes you better at your job. AI, straight out of the box, is effective at simple tasks, but most work people do, especially lawyers and legal professionals, is very complex and customized. AI often struggles with these more challenging tasks, and since that makes up most of what legal teams do, AI hasn’t yet become as useful as it could be. We find that when you properly train AI and create a more active agent, it can assist with more complex tasks. This allows AI to support more parts of your job, not just basic tasks like search and summaries. Our Agent Marko is depicted as a duck, gliding effortlessly on the surface, but paddling like crazy underneath. That’s exactly how working with Agent Marko feels. It’s as simple as sending an email or high-level request for a contract review, but behind the scenes, thousands of prompts run on hundreds of custom instructions written by our lawyers for each client, using the most powerful reasoning models available. That paddling under the surface makes everything seem easy above.
Ari Kaplan: Where can startups most easily distinguish themselves?
Debbie Epstein Henry: Start by understanding what your audience wants. We find that unless you’re designing a service and a tool that truly speaks to your audience, you’ll be at a disadvantage. For example, in our case, we study what clients want in the in-house legal department space. We know they want flat fees. We know they want unlimited users and usage because if we develop a great product that everyone on their team wants to use, the last thing we want is to hinder their use of that tool or have colleagues compete with each other. So the first step is understanding your audience’s needs. The second is to offer a service, rather than just be a software provider. You heard Brian talk about the importance of customization. As AI tools improve, they learn their clients’ preferences and requirements. Providing that customization is essential. The third step is being smart about defining who should do what kinds of work; where you want people involved; where their value lies; and where AI adds value, leveraging the strengths of both. In our case, we have former practicing lawyers on our team, whom we call lawyer-prompt engineers. They communicate with our clients, train our agents to build custom AI playbooks, and handle updates by incorporating client feedback and testing documents to ensure AI playbooks are accurate and current. We rely on the strengths of the team to be truly effective.
Ari Kaplan: What are the misconceptions about AI that leaders need to address before they can achieve broad adoption?
Brian Powers: There are two conflicting misunderstandings, both of which lead to disappointment. One is the belief that AI can do everything straight out of the box, which often results in frustration. The first time you use it, it feels absolutely magical to ask a question and receive an intelligent response. Everything else that could do that was a human. So you assume it can do everything a smart human can do, but you start encountering real limitations when you ask it to do something more customized or complex. The other misunderstanding is that AI can only handle very simple tasks, no matter what you do with it, leading to missed opportunities to leverage AI’s full potential. We see that the reality is a blend of these two ideas. AI chatbots using the models directly are really useful for questions, research, summaries and similar tasks, but for more complex jobs, you need to specify everything you care about and give detailed instructions. That’s exactly what we do at Markups.ai. We provide Agent Marko with hundreds of fully customized instructions for each client’s routine negotiations, enabling it to handle complex agreements faithfully. However, it requires quite a bit of effort, and that’s where we aim to support our clients.
Ari Kaplan: What skills should legal professionals enhance to fuel their success?
Debbie Epstein Henry: This is such an important question because there’s a lot of fear around AI, with many believing everyone’s jobs will be replaced. Focusing on this is really crucial. First and foremost, it’s essential to have the substantive expertise expected of any legal professional in that role. That’s a fundamental requirement. But beyond that, what really matters is developing additional skills that set apart those who thrive in the workplace from those who struggle. These extra skills, in my view, include effectively communicating with confidence, exercising judgment, building relationships, exuding executive presence, establishing trust, cultivating sponsorship, being able to self-advocate without offending, and giving and receiving feedback effectively. Many see these as soft skills, but I believe they are vital to being an effective legal professional. Especially with the growing use of AI, these skills will become more important than ever.
Ari Kaplan: How do you see AI empowering legal professionals as it continues to develop?
Brian Powers: When AI is executed effectively, it allows you to replicate your best work and provides a much greater level of leverage. Everyone wishes they had a highly intelligent assistant capable of handling tasks exactly as they prefer, and AI has that potential. It doesn’t achieve this automatically, but with proper guidance, it can definitely reach that level. AI enables legal professionals to focus on more strategic work, giving them the time to decide how things should be done, rather than just following routine tasks every day, and it can handle tasks that might have previously been done externally or internally. This way, companies can save a significant amount of money while maintaining the same team size. We see our clients doing this, and it’s truly impactful. When AI works well, you can enjoy productivity gains without the huge upfront headache of implementation. That used to be a major sacrifice, but now AI tools are making it easier to start using new technologies, which is really exciting.
Listen to the complete interview at Reinventing Professionals.
Ari Kaplan regularly interviews leaders in the legal industry and in the broader professional services community to share perspective, highlight transformative change and introduce new technology at his blog and on Apple Podcasts.
