Ari Kaplan spoke with Nnamdi Emelifeonwu, CEO, and Bruno Belcastro Pinto, Senior Product Leader of Definely, during the 2025 International Legal Technology Association conference. Here are highlights from the conversation. Definely is an AI-powered productivity suite for contract drafting and review that includes Definely Draft and its new Cascade AI drafting assistant.
Ari Kaplan, Principal, Ari Kaplan Advisors: Tell us about your background and the genesis of Definely.
Nnamdi Emelifeonwu, CEO, Definely: I’m a former lawyer. I trained at Freshfields for about five years, focused on finance-related law. At the firm, I worked with Fergus, another newly qualified solicitor, who was brilliant. What made him unique was that he was one of the few registered blind solicitors in the U.K. His difficulty with reading and understanding lengthy contracts inspired us to find a better and more efficient way for him to access the information he needed to be more productive. That was the spark behind the first product we launched in 2020, which is Definely Draft. Since then, we’ve built a productivity suite that helps lawyers read, understand and draft contracts. We’re very proud that what started with a pain point that was faced by a visually impaired professional is now being used by thousands of lawyers at some of the biggest law firms and organizations around the world, such as A&O Sherman, Slaughter and May, DLA Piper, J.P. Morgan, Barclays and Deloitte.
AK: Bruno, tell us about your background and how Cascade is transforming the contract review process.
Bruno Belcastro Pinto, Senior Product Leader, Definely: I have 12 years of experience building products people love. I come from a pure tech background, and I see a lot of disruption happening in the legal and legal tech sectors, which attracted me to Definely. I joined in early 2025 to lead our teams on the AI side of the company. We launched Cascade at the 2025 ILTA Conference, a product that helps lawyers identify the first, second and third-level knock-on effects of any changes within a legal contract. In contrast to a typical redlining tool, we’re leveraging all the technology we’ve built into Draft and combining it with the power of our agentic framework to augment lawyers, ensuring they can focus on the most valuable work for their clients using Cascade.
AK: What are the most significant barriers preventing law firms from fully embracing AI-driven solutions, and how is Definely helping them through that journey?
Nnamdi Emelifeonwu: Lawyers have historically been skeptical of any tools that could lead to security issues, especially given the sensitive information they handle on a daily basis with their clients. AI clearly is one of those applications where you have to be comfortable with having data being used in places that you may not necessarily ordinarily want it, because of client issues. As law firms interact with vendors and companies, the onus is on the companies to make sure that they have all of the safety standards that are needed to ensure that the data from these law firms is safe. We hold all of our security certifications, providing our clients with the strongest reassurance that their data is being used in the right way. As security increases, law firms and corporate legal teams will become increasingly comfortable with AI adoption.
AK: As the company has continued to grow and launch new products, how have you maintained a consistent user experience?
Bruno Belcastro Pinto: We put our users at the center of everything that we do. We believe that we need to be really deep into their workflows and meet them where they are, rather than trying to take them somewhere else. Context switching is one of the barriers to adoption when it comes to legal tech products. Lawyers live within Word, so that’s where we are and where we meet them. Regarding user experience, we are constantly testing to ensure we are optimizing workflows based on feedback from our customers.
AK: How has Definely been able to achieve its growth milestones?
Nnamdi Emelifeonwu: We’ve been focused on building the best products to solve problems for lawyers, who typically focus on highly complex transactional documents. As a former lawyer, I know the problem that they are trying to solve, and our mission has always been to build beautifully designed, intuitive products. When you strip it all back, a company is just a collection of individuals trying to achieve a goal, and ours is to create incredible products that offer real value to our customers. As long as we continue to do that, we will continue to delight them, win others, and that will allow us to naturally grow. I have also been so lucky to have a very experienced and skilled team around me, which has really helped.
AK: Tell us about the technology on which Cascade is built.
Bruno Belcastro Pinto: In developing Cascade, we worked to understand the logic within contracts, including definitions, clauses and other complex elements associated with legal documents. We also leveraged our model-agnostic agentic AI framework to ensure that we can offer the best model for the best task. We combine that with the technology we built over several years to offer that third-level analysis of any potential knock-on effects of changes.
AK: What skills are most important for your team members as you grow?
Nnamdi Emelifeonwu: Building a successful company is relatively straightforward: Find highly skilled individuals with expertise and experience in a specific area, and then get out of their way and let them do what you hired them to do. As a tech company, we are always seeking the best engineers, product managers and data scientists. However, we are also looking for salespeople and customer success professionals to ensure our customers love our product and service. We also value marketing to enhance our exposure and promote our brand. There are a lot of different facets to a company, and it’s all about finding those people who have the relevant skillset to help you with your ambitions.
AK: What are the challenges of adapting technology to a rapidly changing tech landscape?
Bruno Belcastro Pinto: There are definitely challenges, but there are also lots of opportunities. Our product and engineering teams feel like kids in a candy store with all of the technology advancements associated with AI, machine learning, and large language models. There are many things that are now possible that were not possible even six months ago, and we can expect to see more developments in the next few months. In terms of challenges, data center capacity and the fact that new AI models consume a lot of energy are the main challenges at the moment.
AK: What changes in the practice of law do you see driving interest in technology like Definely going forward?
Nnamdi Emelifeonwu: Some of the currently accessible technology was not available when I started the company, so there’s been a lot of innovation and technological advances over the last few years that have made it more practical for lawyers to embrace technology. There has also been more interest from clients who are now asking their law firms for these tools. For example, generative AI is table stakes, as everyone is expected to be utilizing technology to work in a more efficient way. Law firms are seeking more efficient ways to deliver their services and return greater value to both their clients and employees. This culmination of factors is creating this perfect storm for the legal technology sector.
Ari Kaplan regularly interviews leaders in the legal industry and the broader professional services community to share perspectives, highlight transformative change, and introduce new technology at ReinventingProfessionals.com.
Listen to parts one and two of Ari’s conversation with Nnamdi Emelifeonwu and Bruno Belcastro Pinto on the Reinventing Professionals podcast here.
Read more of Ari’s interviews on Attorney at Work here.
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