Jason Barnwell, Chief Product Officer, Agiloft – Interview Series

Jason Barnwell, Chief Product Officer, Agiloft, brings a rare combination of engineering, legal practice, enterprise software, and legal operations experience to the role. An MIT mechanical engineering graduate and former software engineer who later earned his law degree from USC, Barnwell built a 15-year career at Microsoft, where he held senior legal and operational leadership roles and helped drive the digital transformation of contracting and legal work at enterprise scale. Before joining Agiloft, he also practiced corporate and emerging companies law at Cooley LLP, served on the board of CLOC, and advised legal technology companies including ClearBrief.ai and LawAdvisor Ventures. After joining Agiloft as Chief Legal Officer, Barnwell quickly became deeply involved in product strategy, bringing the perspective of someone who has been the buyer, builder, and practitioner of the kinds of contracting systems Agiloft develops.

Agiloft is a contract lifecycle management company focused on helping enterprises turn contracts from static documents into structured, usable business data. Its platform supports contract creation, negotiation, approval, execution, renewal, obligation tracking, analytics, and integration with enterprise systems, with a no-code architecture designed to adapt to complex legal, procurement, finance, and operations workflows. The company has also been expanding its AI strategy through Agiloft Astra, an AI-powered contract intelligence platform built to make contract data searchable, analyzable, and actionable across the business. By combining CLM, contract analytics, and AI, Agiloft is positioning itself around a broader shift in enterprise contracting: moving from document management toward contract intelligence that can surface risk, improve decisions, and help organizations manage commercial commitments at scale.

You’ve had a uniquely nontraditional path, moving from MIT mechanical engineering and software development into law, leading legal transformation at Microsoft, and now stepping into the Chief Product Officer role at Agiloft. What convinced you to make this transition, and how have those experiences shaped your vision for the future of the platform?

I took on the Chief Product Officer role at Agiloft because it is an opportunity to continue my adventure in a way that lets me contribute and grow even more. Leading our product function advances my life’s work of bringing useful tools to professionals who operate in complex work systems. I want to elevate their craft and help their organizations make better decisions, faster. My path is not traditional, and I bring varied experiences with me. Engineering gave me a builder’s toolbox. Practicing corporate law showed me how faster, better decisions deliver wins. Leading at Microsoft taught me how to scale. These experiences inform Agiloft’s ambition to building a system that turns our customers’ contracts into business intelligence and a control plane that is a strategic operating layer.

You’ve described yourself as both the buyer and the builder of contract technology. How does that perspective change the way you prioritize product decisions compared to a traditional software executive?

Buyers are deeply pragmatic and builders dream. Holding the tension of both personas gives you a realistic view on the frontier. Both what we can build and what is valuable for our customers. My lived experiences help me understand the types of proof a customer expects to see that justify their effort to join our development-to-market journey. I will take product decisions that don’t make sense in a vacuum but are rational under repeat play conditions in the real world, because they demonstrate we are a trustworthy partner focused on shared value. Our customers must win for us to win. My time as a buyer showed me why that partnership matters so much.

During your time at Microsoft, you helped oversee contracting infrastructure tied to billions of dollars in procurement activity. What lessons from operating at that scale are most relevant to enterprise customers today?

Our procurement contracting at Microsoft operated effectively on a massive scale, and that taught me lessons of operation and value. The operation lesson was process controls are key, because if your processes deliver successful output for input and you have mechanisms to adapt those processes with agility you can handle the expected and unexpected demands more gracefully and with confidence. The value lesson was we consistently delivered outcome types to the business that expressed our contribution:

• Speed unlocked every dependent business action that follows;
• Unit cost and capacity created leverage on constrained resources;
• Insights produce business opportunity signals. Contracts are both a business intelligence source and business control plane that every enterprise customer should be using to adapt themselves faster. As an enterprise scales the value of speed, control, and insight compounds.

You’ve referred to yourself as “customer zero” at Agiloft. What insights did you gain by running your own legal department on the platform before taking responsibility for product strategy?

As Agiloft’s CLO I was one of our most demanding customers. We called ourselves “Customer Zero” because we went first. And we had high expectations for reliability, quality, and innovation velocity because we run our legal function on Agiloft’s platform. I was accountable to our CEO with the same expectations as an enterprise customer. I was noisy when something didn’t work the way it should because I saw the ambition and excellence of our product builders. I experienced the challenge of our customers: resource constraints; high expectations; and constant change. And I realized that customers want a partner that helps them drive outcomes by making it easier to navigate those constraints. I know the unlocks that are available within those constraints because my team did unnatural things with our platform. We are going to bring even more product capability to our customers, and we keep discovering that faster because we build Agiloft on Agiloft.

Many vendors are racing to add AI features to contract management platforms. Where do you believe the industry is focusing too heavily on features instead of solving fundamental customer problems?

A feature race delivers busy products that customers struggle to solve real world problems with. It also tends to produce shallower value that does not apply product taste to the customer’s true job-to-be-done. This looks like putting a generative AI layer on top of unstructured contract data and calling it intelligence. If the underlying data is inconsistent or scattered across disconnected systems, you haven’t built a CLM platform. You’ve built an expensive way to get wrong answers, delivered to you confidently.

You’ve argued that AI is only as valuable as the quality of the underlying contract data. Why is structured contract data becoming such a strategic asset for enterprises in the AI era?

You don’t know what you are missing until you structure contract data, see the patterns, and turn those into insights you can do something with. How we structure data, and the specific projections we create reflect our hypotheses of how the clusters of information and how they relate to each other explain what is happening. To get nerdy, structure helps us reduce words that express meaning in higher dimensional space into more compact forms in lower dimensional space that is easier and less expensive for humans and machines to reason over and do something with. So, structure helps us accurately and efficiently deliver actionable intelligence like the ability to measure exposure, model scenarios when conditions shift, understand which commitments you can honor, and which ones create risk that are encoded in your contracts. Organizations that have well-structured data have an advantage that compounds with usage because they have stronger insights and controls.

Agiloft’s Astra platform is designed to make contract information searchable, analyzable, and actionable across departments. How do you see contract intelligence evolving beyond legal teams and becoming a core business function for procurement, finance, and operations?

Contracts document every promise you’ve made to a customer, supplier, or partner, which means they are the connective tissue of how the business runs. Contracts are signal intelligence and a control plane for the enterprise when you can reason over and drive them at-scale, with accuracy. At that point, organizations should stop thinking about CLM as a legal tool and start treating it as an infrastructure for decision making and execution for businesses that cross the organizational boundary. This is how contract intelligence becomes relevant for procurement, finance, and operations. This looks like “can we pursue this revenue”, “can we honor this obligation”, and “can we take on this exposure” as business enabling capabilities that help an organization grow value.

Having spent years applying technology and automation to legal operations before generative AI became mainstream, what current AI trends do you believe are overhyped, and which developments are still being underestimated?

The challenge and potential are intertwined. The challenge remains that tasks are tightly bound to jobs done by humans that exist in systems that create inadequate incentives to spin those tasks off to less resource-scarce approaches like machines. We vastly underestimate how much of each task and how many of those tasks can be done by machines now if we are willing to do some thoughtful redesign that deploys humans in-the-loop, on-the-loop, above-the- loop, or out-of-the loop with thoughtful risk-reward analysis. The net result is that most organizations are using AI to do the old work a little faster between human gates rather than genuinely redesigning how they work and seeing far less value than is available. That’s a sociological problem masquerading as a technical one because the right culture and incentives empower the people closest to the work to change the work. The solution is less managership and more leadership.

You’ve spoken about AI agents and the shift from standalone tools to intelligent systems. How do you envision agentic AI transforming contract lifecycle management over the next five years, and what safeguards will organizations need to put in place?

In five years, we will manage our contract fleets at a much higher level of abstraction. We will define a set of objectives and constraints that describe the outcomes we expect and the characteristics of those outcomes that matter. Effectively, we will define the value functions for our businesses. This is the only way we will handle the volume and complexity that awaits. The regulatory environment is moving faster than most legal teams can manually track. From AI governance to data privacy laws to supply chain compliance. These constraints land in your contracts, and you have to manage them. Astra, Agiloft’s contracts AI platform, is already giving our customers ways to manage their work at a greater scale, but the trajectory points somewhere more ambitious: a system that doesn’t wait to be asked, and we are building for that future now. We will build the transparency and control capabilities customers need into these systems that keep them aligned with customers’ desired value functions and provide elegant ways to validate that alignment. I will offer you an odd notion.

In five years, the bigger risks to businesses might be work that happens outside of these systems. We might discover that scarce and precious human creativity is best directed at the frontier, and our safeguards will look like the thoughtful division of labor in ways that might surprise us.

Looking ahead, what would success look like for you in this new role? When enterprise customers evaluate Agiloft three years from now, what capabilities or outcomes do you hope will clearly differentiate the company from the rest of the legal AI market? 

Agiloft put someone in the product seat who has been an engineer, a practicing attorney, and an operator of enterprise contracting infrastructure, not because those are interesting credentials, but because building AI that actually works for our customers benefits from having lived it. Success for me means honoring that bet by delivering our customers value that makes them say “Wow!” Three years from now, I want every Agiloft customer to be able to solve a business problem that flows through their contracts that seems impossible today. I know we can do that because I have seen what we can do now. We’re going to help our customers take the lid off their ambitions. That’s going to be serious fun. Let’s build!

Thank you for the great interview, readers who wish to learn more should visit Agiloft.