Evan Wong is the co-founder of Checkbox.ai, a no-code solution that digitises complex regulations into automated cloud software. Through its no-code platform, Checkbox’s AI technology allows legal, human resources, and risk and compliance teams to better focus on higher value and strategic work. It’s used by the likes of Allianz, PwC, Air NZ, Telstra as well as government agencies in Australia, New Zealand, Asia and US. Prior to founding Checkbox, Evan started Hero Education, a tutoring business that has mentored 1000+ high school students. This was all done during his time studying a Bachelor of Commerce/Law at UNSW. 

Timestamps:

[1:13] How Evan defines success and his vision for Checkbox

[3:00] Evan’s personal mission in leading and inspiring others 

[4:00 ] Evan’s journey building Hero Education 

[ 7:27] The first two years of building Checkbox and Hero Education during uni 

[10:48] Comparing Evan’s corporate stint with his entrepreneurial pursuits

[11:55] De-risking entrepreneurship before going all-in to building Checkbox

[14:21] The early days of building Checkbox

[ 17:55] Choosing to build legacy technology & improve the enterprise software space 

[19:30] Raising $6.3 pre-series A: Tidal Ventures and Sequoia India’s Surge 

[21:55] Go-to-market strategy: Enterprise top-down sales and product-led growth  

[25:18] No-code revolution and the enterprise software space

[27:10] Evan’s vision for Checkbox 

[28:38] How to identify a compatible co-founder

[33:20] Being a hyper-generalist and validating the problem 

[40:22] Wizard-of- Oz effect: Sales process in the B2B space 

[44:56] Navigating the dark days as a founder

[48:10] Hiring and building great teams 

[50:48 ] Culture at Checkbox 

[56:43] Success and Failures at Checkbox

[1:01:11] Evan’s favourite Australian Startup Success Story 

[1:02:53] Books, podcasts and resources that have shaped the way Evan thinks

[1:04:00] What’s next for Evan? 

References 

TEDx talk: How to Fail at Life Successfully 

Hero Education 

The Hard Thing about Hard Things