“I’m confident we’ll get there”: Checkbox’s CEO on his regtech startup’s Atlassian-sized plans


Checkbox founding team (L-R): James Han, Evan Wong (CEO) and Paul Wenck

Despite having only launched in January, last year, Checkbox has already amassed a small fortune of accolades. Notably, the Sydney-based regtech startup was named Regtech of the Year at the Australian FinTech Awards and Best SaaS Startup at StartCon in Sydney.

In addition, CEO Evan Wong took out the Westpac Innovation Challenge and StartCon Pitch Competition, earning himself a trip to San Francisco, where Checkbox will represent Australia at the forthcoming Startup World Cup.

Most recently, Wong snared Third Place and People’s Choice Award at the GMIC Sydney Pitchub Competition, subsequent to which he was approached by one of the judges – the founder of a VC fund – to discuss investment opportunities.

Wong is quick to point out, however, that Checkbox “isn’t just all show”. Since it officially went live in October, his startup has onboarded more than 30 local and international enterprise customers to its platform, which facilitates the digital transformation of regulation. In addition to insurance companies, consultancies and not-for-profits, the startup’s client base boasts Lexis Nexis as well as some of Australia’s Big 4 accounting firms, Big 6 law firms and Big 4 banks.

According to Wong, the early success of Checkbox has involved “a combination of having the right team to execute plus a bucket-load of passion, sacrifice and hard work… lots and lots of hard work.”

The 24-year-old entrepreneur spoke to Dynamic Business about the genesis of Checkbox, which he co-founded with James Han and Paul Wenck, his big plans for the (to-date) bootstrapped startup and the secret to his success at pitching competitions.

DB: What is the elevator pitch for Checkbox?

Wong: Checkbox is a platform that enables the digital transformation of regulation and compliance processes into business applications in the cloud. Subject-matter experts use our drag and drop interface to build digital solutions without writing a single line of code. Some applications Checkbox has delivered include financial reporting standards (Audit and assurance); legal document automation & eligibility process (Legal); a ratings tool for sustainability (Global Ratings); tax solutions for CGT and FBT (Accountancy); and policy breach assessment (Compliance).

DB: What problem does Checkbox address?

Wong: A lack of IT skills is restricting the ability of professionals to innovate and digitise their expertise – this is the problem we are solving. By using Checkbox, businesses are able to codify and automate their expert decision-making processes to unlock massive productivity, but also create digital solutions which they can then sell to generate new streams of revenue. Although the profile of the people who’ve really been taking to Checkbox are in the professional service space, which covers lawyers, accountants, compliance workers, bankers and more, we’re industry agnostic.

DB: Pre-Checkbox, how were regulations being digitised?

Wong: Digital transformation, by its nature, requires structure and consistency so that rules can be applied to manual processes to make them understood by computers. The tricky thing about regulation is that it is so complex and varies across jurisdictions and disciplines – not to mention that it’s constantly changing. This makes it an extremely arduous mission to “digitise” regulation across the board. To date, this is often done through bespoke software development that tackle a very specific problem for a specific organisation. But even then, bespoke compliance software quickly becomes legacy… so everyone has just become comfortable, though dissatisfied, with using tools like Microsoft Excel and Word to manage regulatory obligations. This is the precise reason why Checkbox was built the way it was.

DB: What motivated you to launch the business?

Wong: In its earliest form, Checkbox was an attempt to solve a problem I was facing in Hero Education, which is the business I founded when I was 17. We provide academic support for high school students in NSW around the HSC. The vision for Hero education is to inspire young people to achieve the best start to their professional career.

The business is still running and very successful but I had found it extremely difficult and confusing to work with regulation whilst running the business and wanted to create a digital solution to this problem. I eventually found out through lots of customer research and interviews that this was a HUGE problem – not just for small businesses but for enterprises and government too.

DB: What do your co-founders bring to Checkbox?

Wong: James, who is our CTO, and Paul, who is our Chair and Commercial Director, are the reason why Checkbox has been so successful to date.

James is the smartest guy you’ll ever meet and has a background in engineering and design. He’s also my best friend of 13 years and I’ve known since the beginning of high school.

Meanwhile, Paul has co-founded multiple B2B online businesses including online fundraising platform Everyday Hero. He brings a wealth of experience to the team and keeps us on track so we can smash our goals.

DB: What’s been the secret to your pitch comp success?

Wong: Checkbox is a very technical product and, admittedly, tackling regulation isn’t the sexiest of topics. What I’ve learnt from pitching and our recent successes is that it is very important to detach yourself from the technical details of the problem you are solving, and the technical details of your product. Instead, focus on the benefits to the customer and take your audience through a journey.

You need to show that you are solving a compelling problem. But most of the time, this problem won’t resonate with every person in your audience so it’s very important that you help them empathise. At the end of the day, a pitch is a show, and that means being engaging. A great pitch takes an uninformed person and allows them to deeply appreciate the problem at hand and genuinely believe that your product is the solution to that problem. Being passionate and having fun in the delivery also helps!

DB: What do you hope to get out of the Startup World Cup?

Wong: We’ve actually got two huge events coming up. One, of course, is the Startup World Cup but before that – at the end of this month – I’ll be heading to Hong Kong for the Fintech Finals, which is another global competition.

The exposure we’ll receive, along with the people I’ll meet, will be well worth both trips. For me, it’s not so much about winning the competitions as it is about getting our name out there and meeting the right people. I also aim to have fun – startups are tough, so you should celebrate successes – and this is a great way to do that.

Regarding the startup World Cup, we’ll be representing Australia, so our mindset is that we want to address the fact that Australia isn’t often thought of as house of technology company. A big success story, of course, is Atlassian and I want us to be seen as the next, upcoming Atlassian. I’m very confident well get there in due course.

DB: What challenges have you faced as Checkbox grows?

Wong: One of the main challenges for Checkbox has been finding the right talent to join our team. This is super difficult when it comes to start-ups because the people in your team really are ‘make or break’. A small team size, a new and still-establishing culture, and so much direction still yet to be made on the product and business, means that every single person in our team of twelve has a huge impact on the success of the company.

Another challenge we’ve faced is keeping up with our fast-growing sales pipeline – a great problem to have I know. But as a startup selling into enterprise, we’ve been pushed to not only develop a flawless enterprise solution, but have been thrown into the deep end to establish pricing, security, training, support and a whole bunch of other operations related processes which we’ve had to set up in a short amount of time in order to support the massive success we’ve had with business development.

DB: Looking ahead, what are your ambitions for Checkbox?

This year is going to be HUGE for Checkbox. We’re already working with companies in Singapore, Hong Kong and the United States so we’re really looking to grow globally really rapidly this coming year. We’re also looking for external investment for the first time to grow our team and penetrate new markets which is very exciting. Our goal is to make Checkbox so simple to use and adaptable that our customers will place our technology at the core of their entire organisation, using us to digitise and automate their entire business model.