The challenge
Tax Traders needed to shift from financial services to fintech, which required adopting new ways of working and accelerating software development. The Taylors wanted to preserve the close-knit culture of their 12-person team while scaling product capability.
What we did
- Facilitated team retreat sessions exploring new mindsets and identifying speed blockers
- Delivered a comprehensive Culture Report highlighting internal and external factors affecting speed
- Designed 'Grey Street', a hyper-focused distraction-free product development environment
- Shaped the three-year strategy and advised on the dual-speed operating model
- Established team collaboration strategies balancing startup agility with fintech precision
What changed
- Team grew from 12 to 35 employees, nearly 3x in headcount
- Successful transition from financial services to agile fintech
- Tax Traders established as an industry leader in tax technology
February 2, 2023
In 2012, Nicola and Josh Taylor founded Tax Traders at their kitchen table, launching a financial services company. However, as their business matured, it became clear that their future lay in financial technology. Shifting from financial services to fintech - with a focus on building software - presented two significant challenges: adopting new ways of working and accelerating software development. To address these, Tax Traders turned to Five.
Preserving Company DNA During Change
At the time, Tax Traders was a close-knit team of 12 with a strong company culture. As the Taylors navigated this pivotal shift, they wanted to ensure their culture - a key component of their identity - remained intact.
Nicola Taylor, one of Tax Traders’ three CEOs, noted Five’s collaborative and empathetic approach: “Nick took the time to deeply understand our company - our values, culture, and aspirations - before making recommendations. His genuine curiosity and humility made a lasting impression.”
This understanding laid the groundwork for a partnership built on trust. Five’s initial contributions included facilitating sessions at the company’s team retreat, exploring new mindsets, and identifying strategies to address key questions: Why so slow? and How can we work faster?
Unlocking Agility for Faster Product Development
Tax Traders’ shift to fintech required more than just cultural alignment-it demanded tangible action to accelerate product development. Despite their efforts, progress on a key product stalled, prompting Nicola to challenge her leadership team with a thought experiment: What if all we did was build this product? This exercise sparked valuable conversations but left one key question unanswered: Why couldn’t they achieve this focus within Tax Traders?
Turning to Five, Nicola posed vulnerable yet vital questions:
- Why aren’t we working faster?
- Is our culture or leadership style impeding progress?
- Are we too risk-averse?
Five’s response was a comprehensive Culture Report, which highlighted internal and external factors affecting speed. These insights prompted Tax Traders to embrace innovative solutions, including simulating startup conditions. The product team adopted a hyper-focused, distraction-free environment - gubbed ‘Grey Street’ - where they worked exclusively on the product, away from typical operational demands.
Nicola described the results: “The team’s energy was electric. They collaborated with startup-level intensity, which led to significant breakthroughs.”
The Challenge of Dual-Speed Organisations
Tax Traders’ journey underscored a unique tension: how to balance startup-like agility with the precision required in a risk-sensitive industry. Tax pooling demands perfection, but innovation thrives on experimentation. Five’s support helped Tax Traders navigate this paradox, enabling them to operate effectively at two speeds. Read more about dual-speed organisations.
Outcomes and Ongoing Partnership
Tax Traders successfully transitioned to an agile fintech company. With 35 team members today, up from 12, they’ve established team collaboration strategies and workflows that enhance both speed and precision. Nicola credits Five’s partnership as instrumental: “Nick’s insights shaped our three-year strategy and continue to guide our growth. His commitment to understanding and amplifying our strengths has been invaluable.”
Tax Traders’ evolution from financial services to fintech is a testament to bold leadership, cultural alignment, and strategic collaboration. With Five’s expertise, they overcame significant challenges to become an agile, innovative leader in their industry. Today, Tax Traders stands as proof that with the right mindset and partnership, even the most complex transformations are achievable.
