The fintech boom: A PE-backed tax journey
Executive summary In this Future of Tax conversation, Ken Chan, Global Head of Tax at Fina...
In this Future of Tax conversation, Ken Chan, Global Head of Tax at Finastra, shares a candid perspective on navigating pace, ambiguity and scale in fintech and financial software businesses. Drawing on his experience building tax functions through periods of hypergrowth and maturity, Ken explores how mission focus, execution and commercial understanding shape effective tax strategy in product‑led organisations. The discussion offers practical insight for senior tax professionals thinking about operating in fintech, scaling teams globally, and aligning tax more closely with business outcomes.
Ken reflects on the differences between early‑stage growth and maturity, the skills needed to thrive in these environments, and why mission focus, execution, and commercial understanding matter more than ever. The result is a practical, first‑hand perspective on how tax teams can deliver impact in one of the most dynamic sectors in the market.
What was particularly interesting, was how clearly he articulated the differences between operating in high‑growth fintech environments and more mature, scaled organisations – and how adaptable tax needs to be in each. Rather than focusing on abstract trends, Ken spoke candidly about pace, ambiguity, execution and the very real trade‑offs tax leaders face when supporting product‑led, mission‑driven businesses.
Ken’s career has been shaped by building tax functions inside fast‑growing fintech and financial software businesses as they scale globally, spending the past five years at Finastra overseeing tax across a complex, international group trusted by financial institutions worldwide.
How do the tax challenges differ between a PE‑backed software group like Finastra and a high‑growth, cross‑border payments fintech like Wise?
During my time at Wise, the organisation was still very much in its relative infancy and experiencing a period of hyper growth. We were trying to fit an evolving set of innovative products into an outdated tax framework. As we continued to launch into new markets, we had to work very closely with the product, engineering, and banking teams as well as frequently engaging and lobbying with finance ministers and tax authorities around the world.
At Finastra, the tax challenges are different and more demanding in its pace and complexity. As a mature business that is trusted by thousands of financial institutions worldwide, there is a significant volume of cross-border considerations, structural tax planning, and value creation initiatives. The challenge here is therefore less about interpretation and more around the efficient management of an complex group at scale and at pace.
Whether it’s delivering speed and convenience at Wise or reliability and security for our customers at Finastra, what brings the two experiences together is the common need to be truly mission focussed.
What aspects of fintech – particularly cross‑border payments and digital platforms – create the most complexity for tax teams and how do you strike the right balance?
Fintech often creates tax complexity because it usually involves constant change, multiple developing revenue streams, digital delivery, and rapid product evolution. Cross‑border payments specifically then trigger the usual questions around VAT recovery and place of supply, withholding taxes, permanent establishments, transfer pricing considerations.
Going back to the previous point – the key to success here is to ensure the purpose of the tax team is seamlessly aligned with the wider organisation’s core mission. This is then the starting point for ruthless prioritisation, ensuring everyone in the team is moving in the same direction at pace, investing (rather than spending) time on the highest impact activities.
What are the biggest challenges you’ve faced scaling the tax function in a global organisation like Finastra?
The velocity of change can be incredibly tough, particularly for passionate tax teams who can’t help but get involved in solving problems. In the past 12 months alone, we have completed an opportunistic refinancing, streamlined our business through the sale of a business unit to Apax as well as our student lending business in Canada, and are now kicking off our tax technology initiative.
Expectations are high and the only direction they are going is up, so my biggest challenge (and reward) right now is trying to continue preserving the tax team’s culture of being able to bring their whole selves to work so that we can focus on just getting things done – all while moving at breakneck speed.
What type of tax professional thrives in a fast‑moving fintech or financial software business?
Anyone who wants to have an opportunity have 10X impact should give it go. I love having a diverse range of people into the team – bringing their unique experiences and insights into how we solve problems for our customers. But what I’ve noticed is that, the folks that have thrived – really thrived – are those that are naturally:
More than anything else, they connect their work to the mission. These are the ones that get why the business exists, the impact we’re having on customers, and why it’s therefore so critical that we execute well and at pace.
How important is commercial and product understanding in companies with models like payments or SaaS?
You could probably get by for a few months without a deep understanding, but gaps and mistakes will soon appear as it becomes apparent that the tax strategy is completely misaligned with the commercial reality.
Similar to the importance of being fully aligned to the mission, it’s critical for the tax team to be fully embedded into the business so that they can understand how and where IP is developed, what truly drives value, the various methods of delivery of the service or product, and the labyrinth within which you must navigate to deliver an exceptional tax strategy.
What mindset shifts are needed for someone moving from a traditional tax role into fintech?
Tax professionals coming from traditional tax backgrounds will need to very quickly shift from “find the rule, apply the rule, document the rule” to a mindset that embraces ambiguity, rapid iteration, and a laser focus on executing well. Here are few key shifts to be aware of and be ready for.
There’s lots of money involved – how do you build credibility with senior leadership and investors early on?
It’s all about really understanding the mission and what truly matters, and then figuring out how you can deliver 10x impact with the limited resources you have – whether that’s protecting the business, creating value, or making it easier to get things done. There’s no silver bullet. Ultimately it’s all about showing up, getting things done, and constantly thinking about how to do it faster and better next time.
How do you approach structuring a tax team in a business that is scaling globally?
It depends on what the tax team wants to deliver for the mission – whether it’s international expansion, product development, or scaling revenue. This will drive the size and make up of the team.
Broadly I like to first start with versatile and curious individuals that are incredibly passionate about the mission and therefore willing to do whatever it takes to get things done. They tend to be excellent at building relationships across the business. As the organisation grows and matures, there will come a time when specialists are needed such as VAT, transfer pricing, and so on.
What capabilities do you prioritise early on when supporting international growth and new product lines?
Genuine passion and resilience for getting things done are absolutely critical early on. This is because the team will inevitably come across overwhelming uncertainty, dive into products to a whole new level of detail, and take strides into unknown areas of tax that they may have never touched before.
Behind all of this is the support of a group of trusted advisors that should and need to be an extension of your tax team. Without this, scaling internationally becomes incredibly difficult and full of unmitigated risks.
How do you decide what to build in‑house versus outsource as complexity increases?
One guiding principle is to keep in house what creates impact that others cannot replicate, and consider outsourcing routine tasks that are repetitive in nature or which requires an unmanageably broad number of jurisdictions. It’s about who can do it better, taking into account cost and efficiency.
For example, compliance tasks can often be outsourced – not because it’s not important, but because I’d rather the team pivot their attention to a different aspect of compliance such as data analytics and insights.
What should tax professionals understand about fintech business models – such as payments platforms like Wise – before making the move?
You need to believe in the mission; in what the group is trying to solve for its customers and the wider world. And beyond the business model itself, making sure they do your diligence on what it’s like to work there – the pace, the competing priorities, the expectations.
Even within fintech business models, each one will have a wildly different working culture. We all spend so much time at work, we might as well find something we love with mature decent human beings – so in that respect I’m incredibly lucky here at Finastra.
Which skills are most valuable for succeeding in a fintech tax role today and what differentiates candidates who succeed from those who struggle?
Looking at some of the current superstars in my team, one of key traits that differentiates them from others is their ability to think and act not as an employee but as a true owner-leader. They simply want to get things done irrespective of their position or what stands in their way.
This is important in all industries, but much more so within a fast moving fintech environment in which you need to genuinely care about the customers and helping other teams get things right even if it’s well beyond their “remit”.
This reframing of leadership and ownership as an attitude rather than a position means that it’s there for the taking for anyone who is hungry enough to succeed – combined with the other two traits mentioned earlier around willingness to roll up your sleeves and a massive dose of humility.
For anyone able to do this, then being a tax professional in the fintech industry can be one of the most exhilarating and rewarding chapters of your professional life.
How are fintech’s modernising tax and using AI for efficiency?
As the industry matures, tax teams will increasingly combine AI, automation, and in-house expertise to navigate complexity, while maintaining flexibility to adapt to new markets and regulations. The future points to tax teams that are faster, smarter, and more integrated, creating both operational efficiency and meaningful business impact.
At Finastra, we’re about to kick off our tax technology journey and I’m excited to be bringing the whole team along over the next 12 months or so to explore the art of the possible with AI, OCR tools, tax provisioning, as well as more basic opportunities to allow us to solve problems faster, easier, and dare I say in a slightly more enjoyable way.
Despite this automation, the personal touch remains critical. AI doesn’t replace the need for judgement, business understanding, and really solid relationships with colleagues across the business. Tax professionals still need to understand how the business operates, the product nuances, and the commercial objectives. So let’s not get too carried away – tax teams are here to stay, and technology will only supercharge the exceptional impact that tax professionals can deliver.
If you would like to take part in the Future of Tax discussion series, get in touch and let’s explore a conversation from your perspective.
