E1: The Origin Story
of Checkbox

And what transformation teams should learn from startups

E1: The Origin Story of Checkbox

And what transformation teams should learn from startups

E1: The Origin Story of Checkbox and Why Startups and Transformation Teams Have Much in Common

apple podcast outside the box podcast
google podcast outside the box podcast
spotify podcast outside the box podcast
What parallels exist between the entrepreneurial world of startup, and the intrapreneurial world of corporate transformation?
On this episode, we chat with Evan Wong, CEO of Checkbox – a no code automation and workflow technology company based in Sydney, Australia. We explore the lessons that he has learnt as the company has grown from an idea to the rapidly scaling company it is today, and how the lessons of startup have helped advise customers in industry who are driving similar entrepreneurial transformation in their organisations.
We talk about:
  • Evan’s favourite tv series
  • How Checkbox started (and how we almost became a tax mobile app)
  • Validation and bringing people along as transformation challenges
  • How to ask the right questions to find pain points
  • What Lean Startup Methodology is and how it relates to transformation
  • Getting to the “next stage” – parallels between startups and corporate
  • The importance of human connection
  • One lesson that Evan wish he’d heard when he started Checkbox
If you would like to connect with the show host or guest you can find them at:
This show would only be possible with listeners like you!
  • If you enjoyed the show, we would love if you could leave us rating or review to help get the word out!
  • If you have a digital transformation story (or know someone who does) feel free to email us at [email protected] – we’d love to hear from you.


Minwoo Yim (Host): [00:00:00] Hi listeners. Welcome to the Outside of the Box podcast. My name is Min and on today’s episode, we have a wonderful guest. His name is Evan Wong and he is the CEO and cofounder of Checkbox.

Evan Wong: [00:00:10] Thanks Min. Pleasure. We’ve swapped seats since the last one.

Minwoo Yim (Host): [00:00:14] So for our listeners, if you haven’t checked out our pilot episode, go ahead.

If you’d like to find out a little bit more about what the outside the box podcast is about. But to start us off Evan, as an icebreaker question, we want to quickly ask. What is one book, movie, or TV series that you’re reading or watching right now?

Evan Wong: [00:00:31] Hmm. not right now, but I want to, I definitely want to talk about it.

I love black mirror like that was a really cool Netflix series. And I love them because, well, I’m a technologist, I love technology, but it really paints also the dark side of technology and it’s a bit freaky but it’s, it’s amazing. Like it’s so crazy how you can see how technology can really affect society.


Minwoo Yim (Host): [00:00:54] that totally creeps me out. When I watched, I think I watched the episode where they were doing, Oh, no spoilers, but if you haven’t watched it, it’s been awhile. The episode where they created that kind of

Evan Wong: [00:01:03] heaven. Oh yeah. Like that mad shit. Yeah. Like you just live your consciousness in the–

Minwoo Yim (Host): [00:01:08] That’s right- so that’s the future of Amazon. Thank you. We’re going to move to the cloud.

Evan Wong: [00:01:13] Oh yeah. Consciousness uploaded to the cloud.

Yeah, that’s it.

Minwoo Yim (Host): [00:01:17] So not to start on too bleak of a note but we’d like to ask on the note of digital, service transformation, you know, our podcast is really about understanding.

The change that knowledge workers are going through, but we thought it’d be really good to start off the podcast series with yourself, given the story of transformation that Checkbox has gone through. And so not, not, not a lot of the listeners know how Checkbox came about and the story of transformation that we’ve gone through in the last few years.

So do you mind sharing a little yeah. About that?

Evan Wong: [00:01:46] Yeah, of course. would love to. So I think I’m all great. Businesses and startups start with the problem that the founder was trying to solve. And at the time I was actually had another business before Checkbox. It was called hero education. It was an education business, not technology.

but at the time I was studying law at university as well. And I found sort of navigating the legal and compliance content around, running a business. Very confusing. you know, I would hire a bunch of people. In fact, that’s, that’s where we kind of started working together, man, you and I were working at hero together.

That’s all right. and, and we will bring on these staff. I was wondering, okay. You know, what sort of obligations legally am I subjected to? And I would jump on the government website, scroll through walls and walls of text, read through all of it and realize that most of it doesn’t even apply to my situation.

And for the things I did, I wasn’t sure if it was exactly the correct thing. So, so when I finished up a university, I thought there must be a more dynamic way, a much more personalized way action-orientated way to deliver legal and compliance content. and that’s how Checkbox actually started. It was how do we take, what is traditionally a very text, heavy policy rule driven sort of, service delivery and create it in a way that’s more, more human.

now. That the interesting thing is that was not the very first like Checkbox today is not the very first idea of Checkbox back then. So a lot of people always ask me, how did you come up with the idea of Checkbox? And my answer was, well, I didn’t, I didn’t come up with this idea. I came up with an idea.

In fact, it was a pretty. Pretty shitty. I did. it was at that time, how do we empower small businesses with a mobile app? Because that was the craze back then. how do we build a mobile app that connects on one aside with the external regulation and then internally with your bookkeeping and your CRM and your business software, to give you a real time checklist of how to stay compliant.

And when I took that out into market, and spoke to kind of small business owners, they were like, Oh yeah, I have this problem. This solution’s great. And I said, okay, great. So how much would you pay for it? And they said zero. Wow. They wouldn’t pay for it. Right. and that’s when I learned very quickly, well, small business owners face the problem, but they, they, they rather increase profit or reduce costs.

They would not really pay for risk mitigation. And so we did what we did in startup, which is called a pivot. We pivoted. And we started to look at franchises for a while because franchises are big enough to have the problem and to pay for it. But small enough at the store level to still struggle with it.

unfortunately that, that in fly as well, because they didn’t really have the burning sort of need for, for transformation, or that culture in that industry. And so we ended up building tax software for a while and that was okay. But fundamentally we got to this point where we realized that we weren’t the experts, we didn’t want to build the content.

I’ll be responsible for it or maintain it. We didn’t want to turn into a Lexus nexus or like a Thomson Reuters. so we decided to build a no-code platform. How do we build the digital leg Lego block to empower the people who already know the content? I have the expertise and the stamp of approval to actually use our mouse sort of platform to build the solutions we wants, wants to build.

And that’s how it got to where we are today. It’s actually through market feedback and really listening to customers.

Minwoo Yim (Host): [00:04:55] Well, it’s been a very exciting journey. And as you mentioned, there’s been many moments of change that Checkbox has gone through.

So looking back, take me through some of the challenges that you faced as you went through that journey of transformation.

Evan Wong: [00:05:08] I think I’ve kind of already alluded to one of the key ones, which is when you go through transformation, you start with a whole bunch of assumptions. Yeah, that’s, that’s, that’s probably the biggest thing. Like you, you start with a whole bunch of assumptions of who are your sort of users or customers, or what is the problem that they actually have is the problem big enough?

are they willing to pay you pay for it? And you know, when you talk about it in the context of corporates, you know, it’s still, you know, your users still have to pay and they pay with time, they pay with changes in behavior. and so the, the biggest challenge is actually that initial validation step, which I think, when I, when I draw the parallel, I guess, between sort of our experience at Checkbox as, as, as a startup or back then as a startup and the corporate that we work with today, it’s have you spent enough time validating the problems.

and, and with the actual users, because often I think people fall into the trap of maybe trying to do transformation in a black box with a bunch of assumptions, perfecting. It is probably what we see a lot of the times trying to get to the perfect solution before even putting it in front of the users and, you know, box built our first idea.

And we poured millions of dollars into that. Very first idea. We wouldn’t you and I wouldn’t be sitting here doing a podcast Checkbox wouldn’t exist right now. so it’s so important to that early stage validation when it’s cheap. Before you go full blast at it. I think that’s one of the biggest challenges.

I think the second challenge, and this is a challenge I’m facing more today. As we becoming more of a mature technology business is how do you, help people take electives along the journey when, when transformation and change happens so quickly, particularly startup, how do you, how do you actually have your team members?

the changemakers together with you on the journey communication, and the ability to sort of have the, those decisions, communicated, and have everyone kind of bought into it as has been super, has been a challenge even for us. and I think when I think about how that applies to the companies that we work with, On on the corporate side, it’s, you know, while you’re doing transformation, are you actually involving all the different stakeholders that may not be part of the core transformation team, but will ultimately need to sign off for, be the ultimate users of whatever you’re transforming.

are you, are you issuing out sort of the, even as simple as the email communications, having kind of work in progress meetings, creating even flyers or videos to help them, you know, come across the line and be bought into the journey.

That’s great. And, and for those two challenges that you mentioned, you’ve already alluded that, not all of our listeners are obviously from a startup background, but certainly the characteristics of transformation in enterprise where a big organization is very similar to some of the challenges that, a startup or a scale it might face as a, as a technology company or any company really.

And on that note, what might be helpful is to kind of understand what were the types of solutions that. You reached out to in particular with those two challenges to overcome them. You know, we talk about people, process and technology being avenues to mediate or, or conduct transformation, but what did you mean?

Yeah. And I think the point that you just made around, corporates and startups is really important because the transformation teams are in some ways their own mini startup in the corporate. Absolutely. And, and, you know, those, those people leading transformation teams are similar to like a founder of have a startup, right.

And it’s a really exciting concept. you get to build your own little startup within, within a larger organization. And so in terms of those two challenges, you know, the, the first one being, how do you actually do the customer validation? And the tools that were used, I think with that, it’s not so much any, you know, I’m not going to give you a silver bullet and say, we use some sort of Excel spreadsheet or, or a template of questions to use it.

It wasn’t that it was more of a mindset at the end of the day. It’s having the mindset of understanding, you know, the users know best and fundamentally, It’s about not the solution. It’s not about the solution. It’s about the problem and the users. And that was actually what got us, got us as Checkbox through the early days.

you know, the process that I talked about before, around, you know, pivoting so often, you know, that was actually an 11 month process. Well, we did, we spent, we did not write a single line of code. We just spoke to customers for 11 months to try and figure out exactly the right problem to solve and the pain points to solve before we actually write our first line of code box.

And, and I think it’s that mindset. now I wouldn’t suggest that you would spend 11 months in a corporate I’m interviewing people before you, you take action. cause I think you, you have a sort of unfair advantage in a corporate, given that you’re closer to the problem and the users than say a startup.

But I do want to emphasize that it is a mindset, as, as I guess the tool, to, to go and, and make sure you validate properly and also be able to, I guess, ask the right questions because there’s no point having conversations with the users, if you’re not asking the right questions. So I guess, how do you ask the right questions?

you want to really be. Again, focusing on the problem as opposed to the solution and also avoid sort of leading questions. So you don’t want to plant ideas and biases in their mind. Do you want to be, want to be asking sort of open questions, instead, like describe a time when, or, can you describe why this, you know, describe the pain in this particular process?

in terms of the second challenge, which is bringing people along. I think I’ve mentioned some, the tools that we’ve seen our customers as corporates use is from ABMS, like an email form or, or pamphlets, or even work in progress meetings, in a startup context. it’s challenging because things move so quickly.

I think it’s really setting up sort of routine. In our context, right? It’s like having those weekly meetings with the core people, whether that’s at the management level, at the board level or at the team level and providing those updates on an agenda to make sure that everyone is across the line when things, when things change.

And of course that’s for the big agenda agenda items, but there’s so many micro decisions that are made as well on, on a daily basis. And we use, you know, forums like, you know, Slack or Microsoft teams as a way to kind of provide that free flow newsfeed as well.

Minwoo Yim (Host): [00:10:51] And just coming back to your mindset, insight around the solution, you mentioned that, the tendency is to move towards a solution side of things.

And actually earlier on you alluded to that kind of perfectionism, a mindset where the solution needs to address everything in the mind of the knowledge worker and what are some, you know, Other mindset or practical tips that you have for people who, you know, may be struggling with thinking in a more scrappy manner, more kind of what’s the, what’s the pain point and how do I actually use the limited resources and time that I have to actually solve this problem?

Evan Wong: [00:11:25] Yep. so I actually did a trip to San Francisco. I think it was in 2019. And I had the privilege of meeting a lot of the early employees or the co founders and the CEOs of a lot of the tech giants, like from Slack to LinkedIn, to Facebook, it was, it was an amazing trip and there was a common theme for why they were successful.

And, the, the word that you just used is interesting. You use the word scrappy. Scrappy was a word that was very much, used in Twitter. when I visited that company there, and I think it plays back to a very fundamental transformation, or if I make it very literal, like startup methodology, there’s something in startup called the lean startup methodology.

So I think a lot of transformation people are familiar with like six Sigma, and like, Prince two sort of project management. And there’s also of course, lean methodology and startups actually created their own version called startup, the lean startup methodology. There’s a whole book on it. but the whole concept is very simple.

Actually. There’s sort of three stages and it’s in a cycle. You have your ideation phase, you’ve got your build. Test, and then you learn back into that build phase. So it’s the idea that you want to run through that cycle as cheaply and as quickly as possible. It’s about the speed in which you get feedback.

Tying back to what I said before to eliminate those assumptions. Right, because in a corporate again, if you’re leading transformation, you know, you’re that mini startup in a corporate, you can’t apply corporate principles. Yes. You have to make start corporate considerations. But in order for you to be successful with trans transformation projects, you do need an element of startup.

Right. And that it’s that lean startup methodology. How do I actually get, you know, create that scrappy, MVP, that minimum viable product or incorporates, we sometimes call it the, the proof of concept, but how do we create that minimum viable product, which is just enough to get you to the next phase? And I want to emphasize that last point actually, to get you to the next phase.

Because often we try to look at transformation as a big bang event that we have to just get to that perfected sort of end state for people to accept it. That’s not true in the same way, then startup with every time we pitch, it’s not a pitch for, you know, your series, a $5 million funding it’s just to get to the next stage.

What, what do you need to get to the next stage? And then that saves will take you to the next, the next kind of stepping stone until you get to the, you know, the $5 million pitch for the, for the series eight. Right? So in the same way in corporate taking that mentality, what, what do you need right now?

Just to get the next stage, the next stage in corporate, be the funding. It might be the people and the resources. it might be just the mandate to actually explore further. It’s not necessarily to get to that final perfected state of the transformed. In a service or product that you’re building.

Minwoo Yim (Host): [00:14:04] Yeah, I like that.

And I like how you mentioned, there’s a very tight marriage between getting to the next phase. And the second point you made earlier around that kind of change management aspect and getting, you know, vying for transformation and how to actually communicate what you’re trying to achieve within an organization.

Those things are very tightly coupled together because often people have a lot of, Doubt or skepticism about new initiatives that challenge the status quo. And so I can, you know, the conversations that we’ve had in industry has really been about starting small, starting scrappy, get that validation, get to the next phase.

And I

Evan Wong: [00:14:37] want to clarify, right? Cause the word scrappy might put a lot of people off. You know, there’s certain areas that you can be scrappy in and certain areas you can’t be. So, you know, you just to be, you just gotta apply your sense of judgment and know what can you get away with?

Like, what is, you know, what is the mustache, what a criticals and what is should haves and really phase out those projects. Because, you know, you don’t want to be scrappy on things. That’s going to completely destroy the project or, or ruin the reputation of the project and yourself, right? So you gotta be quite, quite smart in what you can be scrappy about, and how you build those phases.

Minwoo Yim (Host): [00:15:07] Absolutely one area. I think scrappiness might not be as valid is human connection, investing in human connection and spending time with people, getting them over the line has unanimously being the Mo the biggest–

Evan Wong: [00:15:19] Oh yeah.

Minwoo Yim (Host): [00:15:20] –buy-in method is to spend time with people that understand and practice that empathy to understand how transformation is affecting them across the board.

That’s been sort of like the main feed,

Evan Wong: [00:15:31] I think so. Cause it’s human psychologically. We don’t. Naturally like change change is a risk, it’s a threat. Right. but, but it allows us to grow. Right. And that’s why it’s important to, to, to actually go through transformation and change. Cause we grow, we become better.

but naturally as humans, we don’t like it. So it’s fundamentally a human challenge often. Right. And I think, yeah, I’m sure a lot of the episodes following this, we’ll have this name come up because we hear this all the time, in our conversations with our customers we’re change makers.

Minwoo Yim (Host): [00:15:57] Totally. And I think listeners, if you’re out there wondering how do I actually go about doing things like that state?

Yeah. put because we have so many more episodes coming along, that will, hopefully give you the practical tips on how to actually lead transformation, your organization. Evan closing question. if there was one piece of advice that you would give to your younger self or your team before you went through that journey of transformation,

what would it be?

Evan Wong: [00:16:21] I think the biggest thing for me, if I was to go back and give advice to myself is find someone who has done or gone down this path before. I feel like a lot of the challenges that I’ve faced, I try to take it head on myself without first looking for someone else who has done it before. And, and so therefore you just, you just end up going through the journey of making the same mistakes that other people have already made.

and it’d be so much more efficient to have, you know, that, that sort of, mentor to point you in the right direction. Easier said than done. I think in our context, because we’re building a very specific business, and it’s hard to find that sort of match. And, and that’s not to say I haven’t done that in the past.

I’ve had some incredible, incredible, sort of people who have helped me in the early days of the business. And, I think that’s the beautiful thing about startup, as an industry globally, it’s that founders help founders. and I try to pay it forward all the time now. And, and when people ask me, Evan, w what can I give back to you?

I don’t know how I can repay you for, for the advice I give. And I say to them, look, The only thing you need to do is just pay this forward. When you’re sitting in my seat, I want you to be mentoring the next person. And I think that’s a beautiful culture. And I wish I did that more in our space, I think.

And I think corporates can learn a lot from that as well. a simple, you know, reaching out to, to another company or PR in other organization, that’s, that’s done transformation space. You’ve already done. That’s going to take you a long way.

That’s beautiful. I love that collaboration. If listeners want to connect with you, where’s the best

place to do that?

well, you can just reach out to me directly on LinkedIn. just search up Evan Wong Checkbox. I’m sure. Come up. or you can email me as well. it’s [email protected]

Minwoo Yim (Host): [00:17:50] Fantastic. Thanks so much for coming out, Evan really appreciate it.

Evan Wong: [00:17:53] Thanks for having me, Min.

Subscribe for Upcoming Episodes