When two worlds collide: How Aspire’s Product Lead uses his improv skills to better understand a new generation of entrepreneurs

Can you briefly share your background prior to joining Aspire?

I studied at the National University of Singapore (NUS) where I built a robo advisor for my final year project (FYP). I found finance so fascinating. I decided to go to Deutsche Bank after graduation. I also worked in a big data startup for a while before Aspire.

By March 2020, fintech firms were disrupting traditional finance bit by bit. I landed in Aspire in a role where I could be a part of this movement, namely the Senior Product Manager. Since I joined, I’ve been behind a number of launches such as our Singapore-based all-in-one finance OS, Aspire account, Aspire card, and Aspire integrations with Wise and Xero.  

How did you find out about Aspire? What made you decide to join the team?

It all started with a LinkedIn message from Gio. We then spent 5 months in discussion as we were figuring out what was the best fit for me at Aspire.

What really sealed the deal for me was Aspire’s culture. Gio was super transparent with me about both the good and the imperfections of the company. Aspire was made up of a small team at the time which means you could work directly with the CTO and CEO. Coming from a company with hundreds of thousands of employees, this was a refreshing change as well as a challenge that I knew I needed in the next chapter of my career. To top it off, I had always wanted to be in fintech as it’s a cool space to be in.

In layman terms, what do Product Managers (PM) in a fintech do?

PMs everywhere help to figure out what the company should build (strategy) and then help build it (execution). The first part is done by collecting feedback from different channels ranging from our customers as well as customer service, marketing, sales, engineering, senior management, compliance, legal and so on.

From this feedback, you get both short-term and long-term priorities一a hundred different things that may solve a problem for your customers and add value for them. A PM’s job is to make recommendations on which of the hundred things we should prioritize and align it with the organization’s goals.

At a fintech, the number of stakeholders is a lot more compared to other industries. We’re dealing with people’s money in which the tolerance for error is close to zero.

One of the things we do to ensure that our products are secure enough is a mental exercise that places us in our customer’s shoes. How would I feel if I transfer my entire life savings to my mother and the money fails to reach her in time? Treating every situation like this keeps us grounded and shows us the seriousness of what we help our customers do.

How did your background prepare you for this role? What is your journey like leading up to Aspire?

Admittedly, my background did not prepare me for this role. The only thing I knew was that I knew nothing about the industry or the role I was getting into. That realisation helped me unlearn the working style of a big company, and learn a new style of working very quickly.

My biggest challenge at Aspire is the lack of precedence in the industry for what we’re doing. Fintech, especially Payments, is evolving fast as an industry. We have to move even faster to stay at the forefront. I find the best way to do that is by thinking logically using First Principles.

In short, the First Principles way of thinking believes that to know a subject better is to break it down to its most fundamental elements, before putting them back together. In fact, Tesla’s Elon Musk is known for adopting this philosophy. When I answered the call to join Aspire, I knew that I was going into a completely different company and mentally prepared myself to be moulded.

What’s your life like now in Aspire? Do you have a vision or roadmap of what you’re trying to build?

My life now in Aspire has not changed too much since I started. I joined right before lockdown and unfortunately because of that, I had not met more than half of the people in the Singapore team.

Fortunately, here in Product we have monthly bonding sessions where we religiously attempt to do interesting activities together like muay thai and even an axe throwing session. Recently, we went to one of our PM’s houses and made korean BBQ and vegetarian rendang for everyone. I also go to the office once a week mostly because I get to play table tennis with whoever is up for a match.

Our vision for the Payments team is to enable SMEs to do any and all sorts of payments and to actually do less and get more done. They shouldn’t have to worry about using yet another software, everything should happen at the click of a button. We are pretty gung-ho about user experience. Everything we do at Aspire, we start thinking about it from a user’s point of view (POV). That really sets us apart in terms of culture. It shows in our product that it’s been thought thoroughly from a user’s POV.

One example would be integrations with accounting softwares like Xero, the entire customer experience is in 3 to 4 clicks to connect your Aspire Xero account. Once you do this, you just forget about it. Things just happen and you don’t have to spend any more mental energy on worrying about how it works as it has been automated.

In the early days, you were hailed as the ‘execution machine’. What was the backstory behind that?

I joined Aspire at an amazing point for any PM to be. Aspire was going to launch debit products. Launching anything from 0 to 1 involves a lot of relentless execution. We knew the building blocks that we had to build. On top of that, we had many new customers joining everyday and giving us valuable feedback. My job was to listen to this feedback and move things as fast as possible.

What does it take to be a PM on your team? Aside from ping pong prowess, what are some key qualities/skills you look out for?

The number one quality I look for in a PM is the ability to learn fast.

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The industry is changing so fast and what we’re doing is so new. Regardless of the years of experience you’ve had, you need to learn fast to be able to not just keep up but stay ahead. Besides that, you should be able to step in the shoes of someone else and think from a user’s POV. If you can do that, you’ve done 70% of the job.

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In your years as Product Manager, what are some effective ways to bring out the best in your team?

#1 Start with no constraints in your mind. Think of the best experience you can give to someone to have them love the product. Your imagination should be the only thing stopping you. Once you have defined the best possible experience, work with everyone to make it happen. You’ll often hear “It’s not possible”. Challenge it ruthlessly. Usually, it evolves to “it’s never been done. I’m not sure if it’s possible” → “Could work, we could try it” → “It works!”  

#2 Customer feedback is key. If you work with engineers and designers, they tend to be far removed from customers as they don’t hear customer feedback directly. One of the value-adds you can do as PM is to make sure that everyone around you gets to hear feedback directly.

#3 Constantly think about how to do more with less. Always ask yourself, “What’s the most direct way you can get from Point A to Point B?” Figure out the twists and turns that can delay you and just avoid them at all costs. Most importantly, don’t do anything twice. While this advice is more for PMs, it can still be applied to anyone. More often than not, you can do a 10-minute version, a 1-hour version and a 1-day version of the same thing. Make a conscious choice of which version you’re doing.

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Your role has since evolved to Product Lead since joining Aspire. What are some tips for those looking to take on more responsibilities in Product?

The evolution of my role is probably the hardest transition as there was no formal training for this. I was quite lucky that my manager guided me through this transition. I even tried googling but there’s very few articles on what it’s like to go from being the PM to Product Lead. My tip is to not be afraid to ask for help by clearly informing your manager that you need guidance. That and to not take things too hard as you may not do everything correctly the first time.

You were the Lead Product Manager when we partnered with Wise to launch Aspire’s FX transfers. Take us through that experience. What were some of the highlights and challenges you faced?

There’s been plenty of highlights from my time at Aspire. One of my key takeaways from the FX transfer project is that the world of payments is extremely complicated, especially when it comes to different countries. Wise has done a good job of consolidating all of it. Working with them was a wonderful experience as the team was very professional.

The biggest challenge was to build while wearing multiple hats. I had to think from the user’s POV, engineer it based on how certain things work and at the same time, channel different mindsets and coordinate between the different functions within Aspire as well as externally with the Wise team. I also had to make sure that I was on top of my business-as-usual responsibilities.

But that’s the thrill of a PM as you can never plan your day. Feedback can come in at any time with varying urgency that can potentially disrupt your schedule.

Give us a peek of what you’re like outside of work!

I spend a lot of time doing improv. My improv group does performances at the National Gallery once every couple of months and we’ve even gone to perform at the Singapore and Manila Improv Festivals.

While I enjoy improv, I also find that it helps me at work. Think about it: it’s a bunch of people getting together and making up a scene on the spot based on an audience member’s suggestion. It’s all about letting go of your idea when needed and building on someone else’s idea. I think the role of a PM is pretty similar ;) I don’t cling on to ideas too hard and for that, it has helped me to work better in a team.

If you weren’t a Product Lead, what would you be doing instead?

I’ll probably be spending a lot of time in the mountains in India. I’ve done a mountaineering course and would love to spend my days up there just doing yoga and meditation一everything hippie.