Everyone Ignored In-House Legal. He Built Its Operating System. (Evan Wong)

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Enterprise legal teams are overwhelmed by inbound work they can't see or control — and it slows down the whole business. Most AI companies chase sales and customer support. Evan Wong went after the function they all ignore.

In this episode of We Built It Because We Had To, host Jonathan W. Buckley is joined by Evan Wong, founder of Checkbox — the AI Legal Front Door and Operating System built for enterprise in-house legal teams. Checkbox intakes requests from every channel, automates routine work with AI, and assigns matters automatically based on type and expertise, while giving legal leaders the visibility and metrics to track workload, cycle times, and resources. For the business, that means instant answers, faster turnaround times, and full transparency into where requests stand.

The wedge is the story. Legal ops is one of the least glamorous corners of enterprise software, and enterprise legal teams have historically been invisible inside their own companies — no real operating system to manage the flood of inbound work. Checkbox picked that beachhead deliberately, positioned itself as the front door to the legal function, and earned its way into serious procurement environments: named customers include Analog Devices, SAP, Coca-Cola, and Woolworths — with no IT required to deploy and minimal change management.

Jonathan and Evan get into the origin of that bet — who first convinced Evan that in-house legal was the right beachhead — what early selling looks like when the buyers are lawyers rather than revenue leaders, how Checkbox thinks about applying generative AI to a function most AI companies have ignored, and the growth challenge Evan names candidly: adding revenue at a rapidly increasing rate quarter over quarter to hit growth goals.

Every episode on Apple, Spotify, YouTube, Amazon and more: https://www.WeBuiltItBecauseWeHadTo.com

Connect with Evan Wong: https://www.linkedin.com/in/theevanwong
Checkbox: https://www.checkbox.ai

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Key Takeaways

Checkbox is an AI-powered operating system designed for enterprise in-house legal teams to manage inbound work across multiple channels with automated routing and AI-assisted task completion.

The company targets in-house legal as a deliberately chosen beachhead market that most AI companies ignore, with named customers including Analog Devices, SAP, Coca-Cola, and Woolworths.

Checkbox provides legal leaders with visibility into workload, cycle times, and resource allocation while delivering faster turnaround times and instant answers to requesters.

The platform requires no IT deployment and minimal change management, making adoption easier in enterprise procurement environments.

Frequently Asked Questions

What problem does Checkbox solve for enterprise legal teams?

Checkbox addresses the challenge of overwhelmed in-house legal teams that lack visibility and control over inbound work from multiple channels, slowing down business operations.

Who are some of Checkbox's named customers?

Named customers include Analog Devices, SAP, Coca-Cola, and Woolworths.

What are the key features of Checkbox?

Checkbox intakes requests from every channel, automates routine work with AI, assigns matters based on type and expertise, and provides legal leaders with visibility and metrics on workload, cycle times, and resources.

Why did Evan Wong choose in-house legal as the target market?

In-house legal was chosen as a deliberate beachhead because it is one of the least glamorous corners of enterprise software where legal teams have historically been invisible with no real operating system to manage inbound work.