Checkbox vs LegalGEN
Checkbox
checkbox.aiLegalGEN
legalgen.comSide by side
| Figure | Checkbox | LegalGEN |
|---|---|---|
| Price from | $416.67/mo | $99/mo |
| Free plan | — | — |
| Free trial | Yes | — |
| Open source | — | — |
| Web | Yes | Yes |
| API | Yes | Yes |
| Plans published | 3 | 5 |
| Spec score · Legal Document Automation Software | 9.0 (#1) | 7.3 (#18) |
| Integrations | Native or documented connections include Gmail/Outlook, Slack, Microsoft Teams, Salesforce, Ironclad and Ivo. | LegalGEN lists native integrations with Clio, MyCase, and WealthCounsel, and offers REST API access on White Label or as an add-on for Online Will & Trust subscribers. |
| Purpose | Checkbox structures how legal work enters, moves through, and gets resolved for in-house legal teams. | LegalGEN is an attorney-branded AI platform for estate planning law firms that uses each firm's documents, templates, workflows, and brand to automate estate planning. |
| Support | The integrations page says Checkbox’s team can help with best practices and technical support for custom integrations. | Smart Intake includes email and chat support; Smart Estate Planning includes priority support and an onboarding call. |
Plans
Checkbox
- Starting price$5,000 a year
- CheckboxPriced on request
- Checkbox subscriptionPriced on request
LegalGEN
- Online Will package$29, paid once
- Trust package$49, paid once
- Smart Intake$99 a month
- Smart Estate Planning$275 a month
- White Label Platform$500 a month
In their own words
Checkbox
Checkbox organizes how legal requests enter, move through and reach resolution for in-house legal teams. Requests can come from email, Slack, Microsoft Teams, forms and other channels, then AI classifies and routes them. Matter management keeps documents, conversations, tasks, approvals, ownership, status and deadlines together. Legal teams can create no-code workflows for routing requests, assigning tasks and tracking progress. An AI Agent answers routine legal questions from approved policies and directs employees to self-service tools or the appropriate workflow. Listed integrations include Gmail/Outlook, Slack, Microsoft Teams, Salesforce, Ironclad and Ivo. Native connectors, webhooks and REST APIs support custom connections, with API keys or OAuth for standard integrations. Checkbox lists encryption, patching, antivirus scanning, intrusion detection, penetration testing and vulnerability scanning. It states that it completed a SOC 2 Type II examination and is ISO 27001 certified, with ISO 27017 and ISO 27018 compliance. Pricing is provided on request through an Order, and the software is for business use, not consumers.