Building the Legal Front Door

Hi, it’s Evan here, the CEO and Co-Founder of Checkbox. And I’m incredibly excited to share that we have just raised our USD 23 million Series A to establish a new category of software for enterprise legal teams.

Support teams had Zendesk. Sales had Salesforce. IT had ServiceNow. Each became the defining system of record and engagement for their function, enabling new levels of scale, visibility, and impact. But more than that, each system fundamentally redefined how the function operated. Each of these business functions had its moment of transformation. And legal is next.

Until now, legal has been the last major business function without its own purpose-built platform to orchestrate workflows, manage service delivery, and demonstrate value to the business. This is what we’re building at Checkbox — Agentic Service Management for in-house legal teams — the Legal Front Door.

A turning point in the in-house legal industry

Over the last few years, Contract Lifecycle Management (CLM) software has dominated the in-house legal technology conversation. But CLM only tells part of the story. CLM is contracts-only and whilst that may represent an important part of legal work, it isn’t the only type of work that lawyers do. In reality, in-house legal teams handle a far broader range of responsibilities: reviewing marketing materials, intellectual property requests, litigation, employment issues, compliance, and much more. CLM, as the name suggests, addresses the lifecycle of a contract, but does not address the overall operation of the legal department. In fact, no existing legal tech category today does this well.

But General Counsels are asking for it. In 2023, Gartner shared that one of two major trends that were emerging in the legal tech landscape is that “legal tech buyers are giving more attention to collaboration, workflow/automation and internal work/service management capabilities”. According to the CLOC 2025 State of the Industry Report, 33% of legal teams plan to adopt legal intake and service request technology within the next one to two years, with 66% identifying the automation of legal processes as the top priority.

What’s driving this trend? Why now?

• Legal has become integrated with the rest of enterprise, touching business processes and workflows from every part of the business. Today, legal is no longer just a cost center. It has become a business enabler, and if run ineffectively, a business bottleneck.

• Advances in generative AI have unlocked new viable ways to solve old problems that were too difficult to solve or demanded more change management than companies could bare.

• Demand for legal services continue to outpace the headcount and resources in the legal department. As companies and markets grow, legal must find ways to scale without increasing headcount.

• Metrics and visibility across legal work have become critical for leadership to understand the value of legal and to speak the language of the C-Suite when communicating performance and making data-driven resourcing decisions.

Reimagining how legal operates

Every day, requests of all topics, sizes, urgency, impact, and risk, flow into the legal department from multiple different people, departments and geographies. Some requests take 15 minutes, whilst others take hours. Some requests are urgent but low impact, like an NDA that is blocking a deal, whilst some are important but have timelines measured in months, like due diligence on an M&A transaction.

Yet all of this comes through looking the same. And on email. Slack. Teams. An ever-growing, never-ending queue. Work comes in chronologically, not by priority, and completely unfiltered. It’s no wonder why legal is always overworked and burnt out, yet the business still sees them as a slow-moving bottleneck.

Legal is the most expensive service organization within a company, and yet its service delivery model is the most inefficient compared to its peers in IT, finance, and HR.

At Checkbox, we believe in a different service delivery model for legal. And we’re building the technology to enable it.

Rewind to 2015: Early matter management

Legal teams operate entirely out of enterprise collaboration tools like email, Slack, Teams, or “carrier pigeon”, as one legal team shared with us on a call. Early systems dubbed “matter management” emerged to try bring order to the chaos. An early attempt at creating a system of record for legal work. However, adoption was poor and the industry rejected it. Too much manual data entry. Too much change management for the legal team. Too much focus on the system of record, and not how to get the data in there.

The year was 2025: The right work is going to the right place and solved by the right resource

Legal teams use Checkbox as a “legal front door” for all requests. AI and workflow automation auto-categorize and auto-triage work to the right level of resource to meet each specific request. Self-service tools are available to provide a first line of defense, with automatic escalation paths to lawyers who are no longer working on everything, but just the impactful, important work.

Let’s take a common request that legal teams deal with: Alex from marketing has a sponsorship agreement ready to go but isn’t sure who is authorized to sign.

1. She emails her manager asking for advice on: “who needs to sign this?”: 2 minutes

2. Her manager isn’t sure, forwards it to finance: 2 minutes

3. Finance thinks it’s legal’s call, forwards it to legal: 2 minutes

4. Legal ops logs the request manually and assigns it to an attorney: 4 minutes

5. The attorney checks the signing authority matrix and replies to the manager: 5 minutes

6. The manager relays the answer back to Alex: 1 minute

That’s 6 interruptions. 16 minutes. And potentially days in delay between initial question and final answer for an answer that lives in a PDF. Scale that across hundreds of ‘who signs this?’ questions a month, and you have teams caught up in paper-pushing and a company moving sluggishly for everything that touches legal. Checkbox reduces this to 0 interruptions for the team, and 3 minutes for Alex.

Under this approach, some of our customers have reported up to 50 to 80% of legal work being handled by Checkbox that previously went to the legal team. Less micro-decisions and less interruptions every day means exponentially more productivity.

By 2026: Legal unlocks all data and automation, but without the data entry and change management

Unlike our “matter management” predecessors, we’re meeting the business where they are, conducting intake in the systems that they already work in and in the way they’ve always contacted legal. Intake is now completely seamless, regardless of the system you’re in when you need legal help. Checkbox’s AI Agent is not just creating completely filled-in matters from conversations, it’s also managing the entire lifecycle of the matter from start to close – without human intervention. We call this “touchless ticketing”. A question for legal flows seamlessly from conversation to reporting. The business works the way they want. The legal team works the way they want. And the entire service delivery model is humming in the background.

By 2027: AI is now a co-counsel and humans are in the driver seat

Every question that has ever come into legal, every answer, and everything in between, is now in Checkbox. Legal is a knowledge profession. And Checkbox is not just a system of record, but a system of knowledge. Checkbox AI Agents act more like AI Co-Counsels, drawing patterns, making recommendations, and assisting human lawyers with resolving legal challenges multiple times faster, cheaper, and more effective than before.

By 2028: AI is now in the driver seat and humans are providing oversight

Workflow automation looks completely different. Forms are dead and AI is executing rules-based business processes autonomously. Workflows are compliant by design, driven by rule-abiding technology rather than humans who need to be trained and reminded. There is more legal activity happening than ever before, but much less of it is being handled by humans. Lawyers are completely absolved from low-value work and are working on fewer things, but much more strategic and important things, deeply. Our AI Co-Counsels don’t just make recommendations, they produce a first draft and explain themselves to the human.

Closing Thoughts

Today, Checkbox serves over 100 customers, including SAP, PepsiCo, Analog Devices, Hitachi, Elastic, Circle, and many of the Fortune 500. I’m very proud that beyond helping them build more efficient and fast-moving businesses, we’ve also helped them enable more meaningful work. Because lawyers are too smart, and life is too short.

But every enterprise has a legal department. And every legal department needs a Legal Front Door to operate effectively. We’re talking about hundreds of thousands of legal teams.

Our vision is to become the cornerstone technology for every one of these legal teams.

Each function in the enterprise has undergone transformation, driven by a foundational software that the entire department now runs on. The time for legal is now. And the system for legal is Checkbox.

There’s a lot to get done so I’m going to go back to building. Thanks for reading!

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Relentlessly obsessed,

Evan Wong