A Beyond the Brief Marketing Conversation with Robert Klamser, Chief Revenue Officer, Stretto

Q: Robert, let’s begin with your personal journey. How did you first find your way into the bankruptcy and legal services ecosystem, and what led you to your role at Stretto?

Robert: My path wasn’t exactly planned, which is probably true for a lot of us in this industry. I was a collegiate rower looking for a part-time gig and found a Craigslist posting for data entry that happened to be right next to the boathouse, as luck would have it. That job turned out to be with Eric Kurtzman and Jonathan Carson at KCC, pioneers in using technology to streamline bankruptcy claims and noticing. I was basically their first hire after the receptionist, which meant I had a front-row seat to see how a traditional, paper-heavy industry could be transformed by innovation. After spending 11 years there, the company was sold, and eventually I helped launch another claims and noticing firm, always with this mindset: there’s a smarter way to do things. Stretto was the next evolution, integrating specialized software and legal and banking tools, and eventually expanding our services and technology to broader legal and financial audiences, not just bankruptcy. Now, as Chief Revenue Officer, my days are split between leading teams, developing our go-to-market strategy, and keeping an eye on the next wave of innovation.​

Q: Stretto has seen significant evolution, from deep bankruptcy roots to broader markets. How do you describe what Stretto does today?

Robert: If I’m on a plane and someone asks what I do, I keep it simple: “We provide software and services to the legal community, specializing in bankruptcy, and we are continuing to branch out.” Our solutions touch almost 90% of bankruptcy cases in the U.S. at some point, whether it’s handling complex Chapter 11 corporate restructurings or providing essential case management tools for trustees in Chapter 7 bankruptcy. Our platforms make it possible for attorneys, trustees, and debtors to collaborate, manage information securely, and meet tight regulatory requirements. And because the landscape keeps changing, we’re always planning how to layer new technology and insight onto those foundational services, especially with AI and compliance.

Q: What’s driving the next phase of innovation for Stretto, especially as the industry faces pressure to modernize?

Robert: For us, innovation comes from two directions. First, we’re dedicated to making lawyers’ jobs easier, not replacing them. Precision and accuracy matter, especially when you’re dealing with legal filings, financial data, and compliance. That’s why Stretto Intelligence, our new innovation engine, is so exciting. As Stretto Intelligence’s debut offering, we launched Stretto Conductor, an AI-powered platform for bankruptcy case management and communications. Rather than generative AI that “does the work,” our focus is on AI that supports and streamlines workflows: document analysis, automated citation, and deep research into precedent. And now, with our Research Suite, a platform we acquired and enhanced, we’re adding tools that help attorneys not only find the documents but also understand the nuanced differences between complex cases, such as the debt structures in airline bankruptcies. It’s about transforming raw data into actionable insight.

Q: How does your approach to marketing and storytelling help Stretto stand out in a crowded legal technology space?

Robert: We operate in a world of constant noise, especially for lawyers. Ten years ago, you’d design a website or a stock proposal and let it sit for years. Today, every proposal and every email needs to be customized. AI helps, but it’s people who make it resonate. Our marketing team spends as much time looking ahead and anticipating client needs as they do producing materials. It’s not about sending more; it’s about sending better, curated, and relevant messaging that cuts through the clutter for each specific person or firm. We’ve even seen attorneys turn to consumer platforms like YouTube or TikTok to explain complex legal processes, especially in larger cases that affect everyday people. So yes, the industry is slowly “unbuttoning the tie,” and connecting more directly.

Q: What challenges or opportunities do you see as Stretto expands outside bankruptcy and deeper into areas like student loans, class actions, and compliance?

Robert: The approach really comes down to depth versus breadth. We aim to do a few things exceptionally well, not everything for everyone. For example, take our work in student loans: we brought in true domain experts who grasp not just the legal side, but also the political and economic complexities. For class actions and federal equity receiverships, we’re building the same kind of tailored solutions. We’re not chasing market share just for scale’s sake; we want meaningful impact and real problem-solving for clients who value expertise.

Q: Looking back, who were your mentors or role models, and how have they influenced your leadership at Stretto?

Robert: My first two “real grown-up bosses” at KCC, Eric Kurtzman and Jonathan Carson, changed my life. They were visionaries who proved that entrepreneurship, grit, and a sense of partnership could build something extraordinary from the ground up. I still call them for advice, and their example reminds me to look for strengths in every teammate and to create a culture where people want to build something lasting, together.

Q: As you look ahead, what excites you most about where Stretto is going in 2026?

Robert: I’m genuinely excited about Stretto Intelligence and how we’re leveraging AI to do more than just speed things up. We’re helping attorneys, trustees, and stakeholders make smarter decisions, faster. The industry is ready for tools that not only make sense of mountains of legal data but also enable professionals to see nuances and risks they might otherwise miss. Technology shouldn’t be about replacing expertise but amplifying it.

Q: Finally, any little-known fact about you that our readers might enjoy?

Robert: Well, here’s one: I was a five-day champion on Hollywood Squares in college, and I used those winnings to pay for my honeymoon and the down payment on my condo! It’s a reminder that sometimes saying “yes” to odd opportunities can set your life in a new direction. That same willingness to jump in and learn fuels my work every day.