At a Glance
| Detail | Checkbox | Wakili AI |
|---|---|---|
| Category | Intake & Portals | Intake & Portals |
| Total raised | $27.5M | Not disclosed |
| Rounds tracked | 2 | Not disclosed |
| Latest round | Series A, $23M · Jan 2026 | Not disclosed |
| Last valuation | Not disclosed | Not disclosed |
| Lead investors | Touring Capital, Surge (Sequoia India), Tidal Ventures | Not disclosed |
| Built for | In-house teams | Not disclosed |
| Headquarters | US | Not disclosed |
Funding, Side by Side
Checkbox rounds
- Jan 2026Series A$23M
- Jan 2022Pre-Series A$4.5M
Wakili AI rounds
No public rounds tracked yet.
Our Take
We have not tested these two head to head yet. The numbers above come from public funding announcements. If you use either one, tell us what you found and it may become a Field Note.
Quick Answers
- Which has raised more, Checkbox or Wakili AI?
- Checkbox has raised $27.5M in disclosed funding, compared with no disclosed amount for Wakili AI.
- What is Checkbox best for?
- Checkbox is a legal front door for in-house legal teams that captures, triages, automates and reports on legal requests.
- What is Wakili AI best for?
- Wakili AI offers AI legal assistance tailored to Kenyan law.
Source: Legal Tech Circle funding data, from public announcements. Updated November 11, 2026.