Customer Discovery · Case Study
Closed the first U.S. customers and built a repeatable Fortune 500 legal motion.
- Industry
- Legal Tech
- Funding Stage
- Series A
- Engagement
- Customer Discovery
Checkbox.ai is an Australia-based B2B SaaS startup enabling efficient legal operations through no-code software, letting legal professionals build their own applications for triage, decision support and document automation.
Checkbox raised a $23M Series A led by Touring Capital in early 2026 at a $100M valuation, was named in Gartner's 2025 Hype Cycle for Legal Tech, and serves 100+ enterprise clients including SAP, PepsiCo, Telstra, and Woolworths.
The Challenge
The founding team required experienced personnel to target and learn from ideal buyers in North America. They needed sales talent specialized in B2B market validation and enterprise outbound success, plus a repeatable sales playbook for lead generation and client discovery.
The Solution
Phase 1 deployed a 90-day on-the-ground team that developed outbound strategy for Fortune 500 Legal Executives and a discovery process testing three commercial assumptions. Phase 2 involved researching and approaching 1,000+ contacts via cold outbound, creating sales enablement resources, and defining qualification criteria.
The Results
Phase 1 generated meetings with senior legal leaders, closed an early-adopter customer, and achieved 20% advancement rate with one conversion. Phase 2 secured 60+ conversations, delivered 20 active deals, closed a >$50K customer, and identified that 79% of Legal Ops teams report to General Counsels.
- Qualified opportunities increase: +20%
- Of Legal Ops teams report to General Counsel: 79%
- Of initial conversations advanced: 20%
Evan Wong, CEOIt's been a really good, first class engagement all the way through. Lots of love for the JJ group. You have shown us how regimented, data-centric, and methodical we should be designing our go-to-market and set a standard for us to meet. You've set the bar and it's not easily attainable.
