Jonathan Stark on Harnessing AI and Curiosity to Transform In-House Legal at Dynatrace
- Cosmonauts Team
- Nov 13
- 4 min read
As technology reshapes every corner of business, the role of the in-house legal team has fundamentally shifted. Legal is no longer a support function, but a strategic partner driving digital transformation.
At Dynatrace, Jonathan Stark, Head of Legal & Board Operations, is at the forefront of this movement, systematically aligning legal tech adoption with the company’s broader innovation goals.
In this candid speaker Q&A, Jonathan shares how AI and automation are not just streamlining legal workflows, but actively empowering better, faster decision-making across the enterprise. He also offers critical insights into the challenges of innovation in a cost-conscious environment.
To hear more of Jonathan's perspective on practical, scalable legal tech adoption, he will join the ‘Smarter Contracts: AI-Driven Review and Contracting Innovation’ panel on our In-House Day, November 20th, helping legal teams move beyond the AI buzz and towards tangible, impactful innovation.
How does your legal department align its technology and innovation strategy with the company’s broader digital transformation goals?
JS: At Dynatrace, the legal team views itself as a strategic partner to the business. In my role, I work closely with Dynatrace’s transformation office and business systems teams, and we’re driving change together. We consider the company’s broader innovation roadmap by examining how our legal technology choices, whether it’s driving AI adoption or implementing a new compliance solution, impact the business's own evolution. This involves building processes together and fostering cross-team relationships. Each new tool should streamline processes, cut costs, and reduce friction for our internal stakeholders, enabling us to achieve a greater impact. Dynatrace is fortunate to have a Chief Legal Officer who is open to new ideas and is a collaborative partner. Having that kind of leadership support makes a tremendous difference—it creates space for experimentation, and it empowers the team to think boldly about how legal can lead transformation, not just follow it.
Where do you see in-house legal departments currently sitting on the technology adoption curve—early adopters, mainstream users, or still in the exploratory phase?
JS: I’d say the industry is in a transition period. Some forward-leaning companies have moved beyond 'early adoption' into real, scaled implementation of AI and automation—but most internal legal teams are still experimenting. I think a number of organizations have buyer’s remorse. They reacted to shifts in technology trends and onboarded tools that aren’t providing the return on investment they expected. The legal industry tends to be cautious by nature; however, the speed of technological change, particularly with generative AI, is forcing a shift in mindset. My view is that in-house teams need to move strategically, cautiously, and perform due diligence.
What are you most excited about in in-house legal work given the new technological landscape? Any particular technology that excites you?
JS: I’m most excited about how AI is changing the way we think, not just the way we work. I think AI is giving people a license to explore and try new ways of doing things. I personally love tools that surface insights that would have previously required hours of human review. The future of legal tech isn’t just about efficiency, it’s about better and quicker decision-making. I’m especially interested in tools that can provide data insights, such as combining CLM data with spend analytics to calculate the legal costs associated with negotiating a sales agreement. On a personal note, I love watching my team get excited about new tools or processes that will improve their day-to-day work lives.
What are still some of the biggest pain points for in-house legal when it comes to innovation?
JS: For me, the biggest challenge isn’t a lack of ideas or technology—it’s budget. Innovation in legal often competes with core business investments, and generally, I think most of the legal industry is still fighting the perception that legal is a cost center rather than a value driver. The reality is, meaningful innovation requires upfront investment before the ROI becomes visible. If I took nothing else away from my experience at Amazon, it’s the lesson that data is only powerful when it drives better decisions. It’s not enough to say something will save money or time—you have to show it, quantify it, and connect it to the larger expected outcome.
You’ve had a unique career spanning consulting, operations, and leadership roles. What advice would you give others on career trajectory and development?
JS: Don’t be afraid to explore. Too often, people think of career development as a ladder, when in reality, it’s more like a maze. Before I went to college at 28, I’d already had more jobs than Ernest Hemingway. I worked construction, spent time at a nuclear power plant, was a journalist, built fences, waited tables, and milked cows on a dairy farm. Every one of those jobs taught me something—about people, resilience, and commitment. Those experiences shaped how I lead today. They taught me to stay curious, adapt quickly, and find purpose in my work, regardless of the title. All of those careers, in one way or another, prepared me for what I do now. I always tell others: try something new, and don’t be afraid to be uncomfortable. If you’re curious about AI, learn about it. If you want to understand budgeting or strategy, take a course on Coursera or edX.
And just as importantly, find a passion outside of the office. It doesn’t matter what it is—golf, running, or baking. What matters is that it’s yours. Something that recharges you, challenges you in a different way, and reminds you that your identity is bigger than your title.
Jonathan Stark’s advice for legal professionals to stay curious, embrace discomfort, and cultivate outside passions, underscores that leadership in legal innovation extends far beyond titles and traditional career paths. As AI and analytics continue to transform how legal teams operate, the lessons from Dynatrace offer both inspiration and practical guidance for teams looking to turn technology into a true value driver.
Ready to gain essential strategies for 2026? Jonathan will continue this conversation alongside top legal innovators at Legal Innovators New York, taking place at Latham & Watkins offices on November 19 and 20.
Private practice and in-house legal professionals can attend for free to network with 500+ industry leaders and to gain fresh strategies for 2026.
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