When it comes to the benefits of legal technology, Checkbox takes the proverbial 30,000-foot view.
The company describes its platform as a “legal front door” designed to improve how work enters, flows through, and gets resolved within legal teams — with operational impact that extends across the business.
“You might have an AI drafting assistant, you might have red-lining tools or CLMs, but you’re probably still operating in a chaotic setting,” says Somya Kaushik, the company’s chief legal officer. “You’re still not seeing meaningful efficiency gains, and legal is not perceived as a profit or revenue driver for your organization.”
Checkbox changes this dynamic by tackling one of legal’s biggest operational problems: intake. In many organizations, projects flow into legal through Slack, Teams, emails, or elsewhere, wasting large amounts of time as lawyers process and manage it all.
Checkbox, instead, utilizes agentic AI to function as a gatekeeper for the legal team, sending incoming requests to the proper individuals and automating tasks before they ever reach a lawyer. It’s a path to deep operational change, and customers have reported 50%-80% gains in efficiency, allowing in-house lawyers to focus on the high-level work and business guidance that drive value for their organizations.
“It’s not just about saving time,” Kaushik says. “It’s about structurally changing what reaches legal in the first place.”
Here, we sit down with Kaushik to discuss how Checkbox approaches in-house workflows, what she’s anticipating for the CLOC Global Institute, and the emerging pain points for legal ops professionals.
ATL: We’ve heard a lot in 2026 about how the legal industry has ‘moved from AI experimentation to AI implementation,’ and now we’re eyeing the emerging use cases. Would you expect a lot of discussion around this idea at the CLOC Global Institute? Would you expect to see any different dynamics there when you’re talking about legal operations specifically?
SK: The conversation has clearly moved beyond experimentation and into implementation, but I think legal ops is now facing a deeper question: What does the modern legal team actually need to look like in order to operationalize AI successfully?
In most organizations today, legal ops specializes in finding the right tool, figuring out the right efficiencies, and tracking where there needs to be a tool in a department’s end-to-end matter management. But now organizations are realizing they may need entirely new capabilities — whether that’s legal engineers, AI implementation specialists, or people who can bridge legal, operations, and technology.
There’s also a growing recognition that implementation itself is hard. You’re not just deploying software — you’re changing how legal interacts with the business.
That includes change management, adoption, governance, process redesign, and making sure AI fits into real operational workflows. I think CLOC is where those conversations are really starting to mature.
For Checkbox in particular, I know (CEO Evan Wong) has said customers report a 50% to 80% reduction in work volume. Can you talk a little bit about how you make this happen?
Checkbox acts as a legal front door with AI handling the initial intake process — triaging, prioritizing, and also resolving common legal requests. That’s one way of reducing legal volume 50% or 80%.
That alone removes a tremendous amount of manual overhead from legal teams.
Then there’s workflow automation. NDAs are the obvious example everyone talks about, but customers are automating all kinds of repeatable processes — vendor agreements, conflict reviews, approvals, policy requests, and more.
A lot of legal work today is slowed down not by the legal analysis itself, but by operational friction.
For example, legal gets a request from the commercial side of the business, and it will come in through an email or through Slack or Teams.
Now the team has to figure out where this request lands in priority, what the risk is, who on my team is the appropriate person to take this. Then there’s also time spent understanding the actual facts of what the request is.
So there’s a lot of back and forth of: What’s the deal size? When do we need to close this? Is this required for us to close on our quarter? In global organizations with people working across different time zones, sometimes work doesn’t even start for two or three days.
Checkbox automates much of that intake and context gathering through AI, then launches workflows tailored to the organization’s processes.The biggest efficiency gains in legal don’t come from helping lawyers work slightly faster. They come from reducing the amount of unnecessary work that reaches lawyers in the first place.
What are some emerging concerns regarding technology adoption by legal teams? And how do you see outcomes changing for teams that successfully bring on new tech?
Legal teams often adopt tools for their own efficiency, but in 2026, the legal team really should be focused on technology that helps them keep up with the pace of change across the business.
For example, your marketing team is definitely using AI to create content. And legal should be able to come in and give them a good understanding of copyright protection when you’re using IP. Your engineering team is vibe coding, and they’re creating things so quickly that if you don’t have legal embedded in the R&D process and the launch, you are probably missing out on some data and privacy compliance requirements.
Because the business is moving so fast, the legal team really should be sitting in the center. And that’s why change management is hard when you bring on a tool for legal now, because you’re interacting with so many other departments.
While I think change management is probably the hardest for the legal team, I don’t think I’ve ever met a revenue organization that’s not excited about being able to get their answers through legal more quickly, or especially through an AI agent or through a seamless workflow. So it’s really about legal professionals being able to make that change for themselves.
It also seems that outside counsel management is a big concern for legal ops. Can you share some ways Checkbox fits into a law department that’s tasked with robust outside counsel management?
I was at the ACC Legal Ops conference in Chicago two weeks ago, and I learned that the average legal team is handling less than 50% of their essential matters, their legal spend is greater than 50% of any other business unit in the organization, and their headcount is one-third of the median.
So with those three statistics, I can infer that because headcount is low, there is a budget, but the budget is going to outside counsel instead of hiring more people. They don’t have enough people to cover the essential matters, so they kick it out over to outside counsel, and now they need a tool to govern outside counsel and to manage that spend.
So the issue isn’t just wasted spend — it’s spend pointed at the wrong problem. When legal teams focus on controlling what comes into legal in the first place, the workload becomes far more manageable. AI agents and workflows help protect the front door: filtering, routing, and resolving the work that doesn’t require a lawyer.
That reduces the need to constantly add headcount, so the team can focus on the high-value work that moves the business forward and reduces risk.
At the same time, you rely less on outside counsel because you’re no longer using expensive external support to handle operational overflow. It all ties back to the front door: controlling what comes into legal and automating the repetitive, manual work that consumes the team today.
Are there any other pain points for legal ops professionals that stand out to you that Checkbox is uniquely suited to address?
One major issue is how difficult it is to maintain institutional knowledge.
Legal ops teams are often manually managing playbooks, policies, clause libraries, and workflows — but the business moves faster than those documents can keep up. Updating them is slow, manual, and resource-intensive.
What’s powerful about Checkbox is that the AI agent can learn through real-time corrections. If a workflow or response is outdated, legal professionals can update it directly in the system, and that knowledge is immediately reflected moving forward.
That’s important because many AI tools still rely on static documentation that’s already out of date.
Anything else you’d like conference attendees to know about Checkbox and how it supports legal ops?
Another pain point we address is manual status tracking.
In most matter management systems, attorneys or legal ops teams still have to manually update statuses like “in progress” or “pending assignment.” Checkbox automates those updates in real time by pulling signals from emails, Slack, workflows, and AI interactions.
That means teams always have live visibility into where matters stand without constant follow-up questions like, “What’s the status of this contract?” or “Where are we in this deal?”
I’ve read a statistic that if you’re interrupted in the middle of a task, no matter how short the interruption, it takes you something like 20 minutes to get back to it.
It does. Context switching is so hard. And the fact that you have to take a moment to think about another entirely different subject, and then go right back into this deep dive zone that you might’ve been in, it is really hard.
One of the biggest benefits of Checkbox is removing a lot of those day-to-day interruptions entirely. People do their best work when they can stay in the zone or in a true flow state — and that’s becoming harder and harder without automation and better operational guardrails.
We always ask around conferences about seeing the local sights. I guess you’re probably not planning to tour Chicago since you live there, but do you have any recommendations for folks from out of town?
I would say if the weather’s nice, you absolutely need to do the architecture boat tour. I know it’s kind of a cliche and many people are going to hear that, but it’s true. It’s really great.
I used to live in New York City, and I love that city. It’s near and dear to my heart, but the architecture of Chicago is just so beautiful and it has so much history, and the history behind Chicago was so lovely and actually very inspiring. So definitely do that.