Checkbox
Checkbox sells AI-powered software to automate legal workflows for corporate legal teams. The company has raised $29M and employs 94 people.
The growth story
Checkbox grew from 26 to 94 employees between 2021 and 2026, raising $29M along the way, most recently a Series A in January 2026.
About
Checkbox provides software that helps corporate legal departments automate repetitive tasks like document processing and request tracking. Its tools aim to reduce manual work while maintaining existing workflows, targeting general counsels and legal operations teams at companies like SAP and Hitachi.
The company raised $29M in a Series A round in January 2026. With 94 employees, its engineering team is the largest function, accounting for over a quarter of its workforce.
Founders and leadership
Engineering is Checkbox's largest department with 24 staff, representing over 25% of the company. The median employee tenure is 2 years, suggesting moderate turnover.
The Checkbox org chart
Evan Wong (Co-founder | CEO) leads 25 mapped leaders with 2 direct reports. Click +N to expand a team; names link to the person’s public profile.
Departments, and which ones grew
Headcount by function: Engineering 26 (+53% YoY), Sales 14 (+100% YoY), Business Development 11 (+175% YoY), Legal 6 (+500% YoY), Information Technology 5 (+67% YoY), Marketing 5 (-17% YoY).
Talent flow
Checkbox recruits heavily from legal tech firms like NetDocuments and Mitratech. Its alumni often move to major tech companies, with Atlassian and Microsoft being top destinations. UNSW is the most common educational background among employees.
Most common previous employers of Checkbox staff: NetDocuments (5), Mitratech (3), Aquant (3), UNSW (3), Stake (2), Opus Recruitment Solutions (2). Former Checkbox employees most often moved to Atlassian (3), Microsoft (2), PlayHQ Sports (2), Salesforce (2), Syncly (2), Thomson Reuters (2).
Alumni worth knowing
The Checkbox mafia
Checkbox alumni have founded 7 companies, including HotDoc, which employs 91 people, and Syncly, which has 23 staff.
8David Parfett, was Board Adviser until 2021Stewart Rasmussen, was Head of Sales until 2020Robbie S., was Vice President of Sales until 2020Alex Kosheliev, was Senior Solutions Engineer until 2021Quinn L., was Solutions Architect until 2018Jacob Pira, was Back-End Engineer (Go Developer) until 2018
Anthony Hien Vu, was Senior Full Stack Software Engineer / Software Engineering Delivery Manager until 2022
Hiring now
Web traffic
Traffic mix: 46% direct, 39% search, 6% social, 1% paid.
What this company is made of
Most common skills at Checkbox: Customer Service (33), Leadership (32), Management (30), Sales (27), Microsoft Office (25), Marketing (24), JavaScript (23), Project Management (22).
Where the team actually sits
Checkbox people are concentrated in New South Wales, Australia (16), New York, United States (11), Illinois, United States (3), United States (3). 2 offices on record.
Search footprint
Checkbox attracts about 907 organic search visits a month, traffic worth roughly $43K a month if bought through ads. It gained 747 ranking keywords and lost 475 in the last period.
What employees say
- Compensation
- 4.60 / 5
- Career opportunities
- 4.90 / 5
- Senior management
- 4.70 / 5
- Work-life balance
- 4.50 / 5
Frequently asked
Checkbox has 94 employees as of September 2026.
Checkbox has raised $29M in total, most recently a Series A round in January 2026.
Checkbox was founded in 2016 by Evan Wong, James Han.
Evan Wong (Co-founder | CEO) sits at the top of Checkbox's reporting structure, with 2 direct reports.
The most common previous employers of current Checkbox staff are NetDocuments (5 people), Mitratech (3 people), Aquant (3 people).
Former Checkbox employees most often move to Atlassian (3), Microsoft (2), PlayHQ Sports (2).
At least 7 companies have a founder who previously worked at Checkbox, including HotDoc, Syncly, AniccaDigital.io.
Checkbox attracts about 907 organic search visits a month, worth roughly $43K a month in equivalent ad spend.
The most common skills among Checkbox staff are Customer Service, Leadership, Management, Sales, Microsoft Office.
Checkbox staff are concentrated in New South Wales, Australia (16), New York, United States (11), Illinois, United States (3).
Checkbox has about 26 people in Engineering, up 53% over the past year, as of September 2026.
Checkbox has about 14 people in Sales, up 100% over the past year, as of September 2026.
Computed from 70 current and 98 former Checkbox profiles, as of September 2026. Source: Crustdata.
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