The Buy & Build Evolution
13 October, 2025
Building FinTech Sales Success
In the latest episode of FinTech Focus TV, Toby welcomes James Dawson, CEO and Founder of Humble Technology, for a deep dive into the realities of sales leadership, growth culture, and commercial excellence across the FinTech industry. This conversation explores how the right mindset, structure, and hiring decisions can transform sales teams, and how humility and discipline are essential in scaling sustainably.
James’ story is one that many FinTech leaders will find both familiar and inspiring. From his early years in trading technology to becoming a sought-after fractional Chief Revenue Officer, James has seen every angle of the sales journey. His lessons in leadership and sales culture come not from theory, but from years of experience across major institutions like ICAP, OpenFin, and Adaptive, culminating in the creation of Humble Technology.
This episode is a masterclass in FinTech sales leadership, offering tangible insights for scale-up founders, CROs, and ambitious sales professionals across the sector.
From Trading Floors to FinTech Leadership
James began his career in South Africa before moving to the UK in 1997. His first role was with HSBC, and after spending two years in Paris setting up government bond businesses and risk platforms, he returned to London to work on front-office trading technology. His next move was to BrokerTec, where he designed European products and helped build operations before the company was sold to ICAP for $500 million.
At ICAP, James thrived in what he calls a “golden era” of trading technology. He launched numerous platforms, including a credit default swap product that went from zero to $500 million in revenue in just over three years. This success, however, also brought a sense of overconfidence, a trait he now reflects on as part of his journey toward humility.
When James joined OpenFin, his perception of sales was completely redefined. Selling enterprise SaaS into major banks was a different challenge altogether. Unlike his previous roles, this wasn’t about providing access to data or trading platforms, it was about navigating complex, multi-stakeholder sales cycles within financial institutions. It took him 13 months to close his first deal, and that experience became a pivotal moment in his career. “I was humbled,” James admits, and it’s this humility that later inspired the name of Humble Technology.
Learning from FinTech’s Best: The OpenFin and Adaptive Years
At OpenFin, James learned the art of enterprise SaaS sales through experience. The long cycles, multiple decision-makers, and intricate buying processes demanded a new level of discipline. Yet, with persistence and refinement, he began closing deals with leading banks and helping to cement OpenFin’s reputation as a market innovator.
His time there also led to an invaluable collaboration with Matt Barrett, CEO of Adaptive Financial Consulting. The two worked together to create compelling demos that helped win major trading platform contracts. As James recalls, “I was running around showing his demo to all my clients, I got him some really big deals, not even looking for commission.” That partnership evolved into a working relationship when James later joined Adaptive part-time, helping to secure further large-scale deals and scale commercial performance.
These experiences, across both sales and product-focused businesses, provided the foundation for what would become Humble Technology. When the pandemic disrupted his plans to focus on his hospitality ventures, James found himself advising FinTech CEOs on sales enablement and go-to-market strategy. He quickly realised that while he was a strong sales leader, teaching others required structure.
The Birth of Humble Technology and the Value of a Sales Framework
The creation of Humble Technology came from a simple but powerful observation: most FinTech founders are brilliant technologists or product experts, but they struggle with the commercial side of scaling. They often make the same mistakes, hiring the wrong people, scaling too fast, or mismanaging investor pressure, all of which can derail even the most promising businesses.
To tackle this, James spent the rest of 2020 immersed in research. He read every book and listened to every podcast he could find on sales methodology. Among the most influential was The Qualified Sales Leader by John McMahon and the Revenue Builders Podcast, which introduced him to the MEDDIC (later MEDDPICC) qualification framework.
James combined this structure with value-based selling principles, a modern approach that focuses on demonstrating customer success rather than chasing transactions. “It’s not about convincing people to buy stuff they don’t want,” he explains. “It’s about building relationships by relentlessly showing value over 12 to 24 months.”
That philosophy now defines Humble Technology. The firm partners with FinTech scale-ups that have achieved product-market fit and want to grow from £5 million to £20 million and beyond. Through sales audits, playbook creation, and coaching, James helps these businesses identify inefficiencies, build accountability, and accelerate revenue with integrity.
FinTech Sales Leadership and the Power of Culture
One of the central themes of this episode is sales culture, a subject James is deeply passionate about. He argues that culture often determines performance more than product or market conditions. “No one’s ever going to hire me to fix culture,” he laughs, “but one of the first things I do is look at it.”
James has seen both sides of the spectrum. In healthy sales cultures, teams are motivated, collaborative, and proud of their success. They celebrate wins, learn from losses, and support each other. In toxic ones, fear dominates. “I interviewed a salesperson once who said that before Monday morning meetings, he’d go to the bathroom to throw up,” James shares. “That’s how terrified he was.”
This type of culture, driven by pressure from investors or product-led CEOs who don’t understand sales, destroys performance. The role of the CRO or sales leader, therefore, is to shield their team from unnecessary pressure, coach them through deals, and protect their confidence. Sales is inherently tough, rejection is constant, and the best leaders help their teams develop resilience, focus, and pride.
This focus on mindset links back to James’ belief that humility, coachability, and accountability are non-negotiable traits in sales leadership. “A great sales leader is someone who’s always learning,” he says. “They’re humble, they’re coachable, and they create an environment where people can grow.”
Scaling FinTech Sales Teams the Right Way
When it comes to scaling, James believes many FinTechs make the same mistake: hiring too fast. Often, product-focused founders raise capital, hire dozens of salespeople, and assume growth will follow. But without structure, training, or a proven playbook, the result is chaos.
“The first thing I do when I work with a company is a sales audit,” James explains. “I check what’s working, what’s not, what qualification methodologies they’re using, and whether the right people are in the right roles.”
From there, he helps teams develop a sales playbook that defines who they’re selling to, how they sell, and what value they deliver. “If your software costs £500,000 a year, it has to deliver at least £5 million worth of value,” he says. That clarity ensures every salesperson understands not just the product, but the business impact it creates.
James also challenges one of the most common misconceptions in FinTech sales hiring, that experience at a big-name company automatically translates into success. “Hiring someone because they’ve got a big logo on their CV doesn’t mean they’ll thrive in a start-up,” he warns. “They might be used to selling with huge resources behind them. Selling for a scale-up is a completely different job.”
Hiring FinTech Sales Talent with the Right Mindset
James’ hiring philosophy mirrors Harrington Starr’s own experience in FinTech recruitment, that mindset and adaptability are more important than brand names on a CV.
For him, the ideal salesperson demonstrates what he calls “extreme ownership”. These are people who take full responsibility for learning the product, understanding the market, and driving deals forward. “If I see someone making excuses, saying marketing hasn’t sent them collateral, or tech hasn’t sent an architecture diagram, that’s a red flag,” he says. “Go sit next to the tech guy until you get what you need. Make your own PDF if you have to.”
He contrasts this with the “weak mindset” that plagues many underperforming teams. Successful salespeople, by contrast, are relentless, proactive, and dissatisfied with the status quo. They display urgency, intensity, and what he calls “healthy paranoia”.
From a recruitment perspective, James’ process is highly structured. He uses ten objective criteria to assess every salesperson, from mindset and coachability to activity levels and cultural fit. Within three months, if they’re not meeting those expectations, he advises parting ways. “It’s not about waiting for results, it’s about measuring the behaviours that lead to them,” he notes.
Lessons in FinTech Hiring and Retention
The discussion naturally turned to one of Toby’s favourite topics: FinTech hiring. Both he and James agreed that sales recruitment is one of the hardest areas to get right. Interviews can be misleading, especially when candidates know how to “sell” themselves. Many leaders, eager for results, project their hopes onto candidates and overlook potential red flags.
James’ approach to fixing this is refreshingly methodical. “Don’t interview someone around their CV,” he says. “Interview them around your spec, the kind of salesperson who will be awesome at selling your stuff.” That means defining the ideal profile in advance and evaluating candidates against it, not their past employers.
He also warns against over-reliance on inbound candidates. “If you’re hiring through job ads, 90% of applicants will be people who are out of work or about to be fired,” he explains. “If you want great people, you need to go find them, the ones who are happy, successful, and have pipelines full of deals.”
This is where FinTech recruitment partners like Harrington Starr can play a critical role, identifying, engaging, and securing high-performing sales professionals who might not be actively looking but are open to the right opportunity.
Creating an Environment Where Success Is Inevitable
As the conversation drew to a close, James shared one of his favourite concepts: customer centricity. In his view, every FinTech has two customers, the external clients and the internal sales team. “The whole company’s purpose should be to please both,” he says. “If your business is built around enabling your salespeople and making them happy, they’ll look after your clients.”
He also referenced the book The Customer Catalyst and a concept from sports psychology that Toby echoed, the idea of “creating an environment where success is inevitable.” Whether in elite sports or FinTech, the principle is the same: people perform best when given the structure, trust, and support to do their best work.
For James, that’s what Humble Technology represents. It’s not just about improving sales metrics, it’s about helping FinTech businesses grow with integrity, discipline, and purpose.
FinTech Sales, Leadership, and Recruitment: A Unified Message
Throughout this episode, one theme stood out above all others: great sales performance starts with great people. From hiring and coaching to culture and process, the human element remains at the core of success in FinTech.
At Harrington Starr, this belief echoes across our own work in FinTech recruitment. We see daily how the right sales leaders and commercial teams can transform a company’s trajectory. As James Dawson and Toby emphasise in this episode, hiring for mindset, structure, and humility isn’t just good practice, it’s essential for long-term success.
Whether you’re scaling your first FinTech or rethinking your commercial strategy, the lessons shared by Humble Technology's founder offer invaluable guidance: focus on value, culture, and continuous improvement, and you’ll create an environment where success truly becomes inevitable.
