Today’s newsletter features an interview with Paladin CEO Kristen Sonday on building the infrastructure layer for pro bono legal access; a Chicago Creator Hackathon next week for AI-curious builders; open engineer roles at Waymo and Mucker Capital via OneTwoLoop; and events like the OpenAI Forum Chicago and GitHub Copilot Dev Day

Most people who need a lawyer can't get one. Not because attorneys aren't willing to help, but because no one built the infrastructure to connect them. Kristen Sonday did. As CEO of Paladin, she's turning pro bono from a professional obligation into an operating system, one that's already moving the needle on access to justice at scale.

Here’s our conversation:

KS: For context, every lawyer in the U.S. has a professional responsibility to do 50 hours of pro bono work per year - free legal help for low income people. However, there hadn’t really been any tech infrastructure to support the market. At a high level, Paladin is the infrastructure layer connecting lawyers to pro bono opportunities.

There are three main components: a centralized marketplace of vetted opportunities, a matching system that aligns those opportunities with attorney interests and skills, and a reporting layer that allows organizations to manage, track, and scale their programs. Together, that turns what was previously fragmented into something operational and measurable.

KS: The insight was that the problem wasn't about willingness: lawyers wanted to do pro bono work, and legal aid organizations needed help desperately. The gap was operational. There was no infrastructure connecting them efficiently. Law firms had attorneys with capacity and skills, but no easy way to surface the right opportunities at the right time. Legal aid organizations had cases but no scalable way to recruit and manage volunteer attorneys.

The first wedge was building a simple intake and matching layer that made it easy for both sides to participate without adding burden to either. When you remove friction, behavior changes quickly.

KS: The supply of pro bono cases from legal services organizations is infinitely easier because the demand for legal help is overwhelming. The harder side is engaging lawyers, consistently. We focused early on creating high-quality, well-defined opportunities so that when lawyers came to the platform, the experience felt clear and actionable. That initial quality was critical to building trust and driving repeat engagement.

“Good matching” is about finding a well-aligned lawyer for each pro bono client. The attorney doesn’t have to be an expert straight away, but he or she has to be willing to learn, communicative, have time to dedicate, and have empathy for the client’s situation. Beyond that, during the actual matching process, clarity is incredibly important: lawyers need to understand exactly what they’re signing up for. When those variables align, participation increases and outcomes improve.

For volunteer attorneys, we look at Paladin activation rates, their pro bono engagement, and repeat engagement. For organizations, we track program growth (in terms of hours and number of cases per year), and reporting completeness. For legal aid organizations, we’re tracking the frequency of posts and number of placements to determine how helpful we are to them in being able to increase capacity and find new volunteers. Ultimately, the signal is whether more lawyers are consistently engaging with high-quality opportunities over time.

KS: Techstars was formative because it compressed years of learning into a few months. The biggest takeaways were around speed and accountability; how quickly you can test, iterate, and adjust when you’re in constant feedback loops and accountable to a group outside your team? It also reinforced the importance of community. Building a company is inherently unnerving, and being surrounded by other founders navigating similar challenges created perspective.

KS: The acquisition was about expanding from a marketplace into a full operating system for pro bono. Pro Bono Manager brought deeper workflow, tracking, and reporting capabilities. Combined with Paladin’s network, it allows firms not just to find opportunities, but also to manage and measure their programs end-to-end.

KS: My dream is to essentially build the pro bono OS from beginning to end. Starting with a system that conducts better client intake, vetting, and referrals for legal services organizations, to ensuring they navigate to the best resource for them (whether legal aid, a pro bono lawyer, or self-help guides), and then integrating existing AI tools with subject matter expertise that can increase the efficiency and effectiveness with which these cases are completed. The goal at the end of the is to help as many clients in need as possible, and an integration, navigable tech stack would help us significantly close the justice gap at scale.

We’re currently exploring where AI can be most effective throughout the pro bono process before integrating it into workflows too deeply. Client intake, vetting, and initial legal navigation seem like natural points for AI to assist, as well as in pro bono matching and program analysis. Where we’re cautious is anything that touches legal judgment or client outcomes. In those areas, AI should support, not replace, human decision-making.

KS: What stands out is how invisible the infrastructure becomes, in a good way! When the product is working, no one is thinking about the software. An attorney found a case that matched their skills, a person in need got representation, and a legal aid organization didn't have to spend three hours on the phone making it happen. The system just worked. As a builder, that's the goal and it's also the hardest thing to achieve, because it requires every piece of the workflow to be tight enough that none of it creates friction.

The other thing that strikes me in those moments is the distance between the problem and the solution. The person who needed legal help had no idea what was happening on the backend: the firm credentialing, the conflict checks, the matter tracking. They just got a call from a lawyer. That gap between complexity and simplicity is where I think the real product work lives, and it's something we're still pushing on.

Pro bono management ran on spreadsheets and email for decades because no one was looking at it as a product problem. When you find a workflow that sophisticated people are still doing manually, that's usually a signal worth paying attention to.

Calling all Chicago content creators.

On Sunday, April 26 from 11am to 2pm, we're hosting a vibe-coded session built for builders who want dedicated time to learn AI tools and actually make something with them.

The room will be curated.

Think top creators and mentors, a structured agenda that runs from collab connect to show and tell, and hands-on time with tools like Replit and Claude Code. We’ll go from ideation to execution in three hours.

This is for you if you're a creator, founder, or builder with an existing platform who's AI-curious and likes working alongside other people.

Space is limited. Request your spot below.

Follow me on Twitter and Instagram