Fintechs are pulling ahead with faster execution, stronger brands and better customer experiences. In the fintech vs. legacy battle, incumbents need to rethink how they operate and show up—across every touchpoint.
The “David vs. Goliath” trope is a fine, inspiring tale of the little guy persevering against all odds. But in financial services today, the story feels far less romantic—especially if you’re the incumbent.
Traditional financial institutions are under mounting pressure to modernize as fintech challengers continue to reset customer expectations. Across retail banking, insurance, lending and payments, fintechs have set a new bar for speed, seamless UX, hyper-personalization and product innovation. What once differentiated legacy institutions—scale, stability and history—no longer guarantees loyalty.
Nowhere is this more apparent than in financial services. Seemingly overnight, legacy banks and insurance providers found their century-plus of industry dominance challenged by upstart fintechs. Now, simply being established isn’t enough. While challenger banks generated $20.4 billion in 2019 (compared to Sunlife Financial’s $30 billion alone), they’re predicted to reach nearly half a trillion dollars by 2027. Disruptors like KOHO, Simplii and EQ are eliminating brick & mortar, launching user-friendly apps and cutting costs to win younger generations.
But this shift isn’t just technological—it’s cultural. Fintechs aren’t only building better products; they’re building more compelling brands. They speak like humans, not institutions. They take creative risks. They show up consistently across digital, social and even out-of-home channels with bold, recognizable identities. In short, they feel closer, more relevant—and, increasingly, more appealing—to modern consumers.
So what can legacy Goliaths do about it?
Get creative that moves at challenger speed
See how Superside helps legacy institutions modernize, and helps challengers scale creative without slowing down.
Two different playbooks: Fintechs vs. legacy institutions
The tension between legacy institutions and fintech challengers isn’t just operational—it’s deeply structural.
Fintech companies are typically built for speed. Their organizations prioritize rapid iteration, growth and experimentation, allowing them to launch new features quickly and constantly refine the customer experience. Product teams are tightly integrated with design and engineering, and often closely aligned with brand and marketing, allowing decisions to move from concept to deployment—and into market-facing creative—in weeks rather than months.
Legacy financial institutions operate under a very different set of priorities—both operationally and from a brand perspective. Their competitive advantage has historically been built on trust, stability and regulatory rigor. Large banks and insurers must maintain global brand consistency, navigate complex compliance frameworks and manage risk across enormous customer bases. As a result, every change—from marketing campaigns to product launches—often requires multiple layers of review and coordination.
Neither model is inherently better. Fintechs win attention because they feel modern, intuitive and frictionless—not just in their products, but in their tone, visual identity and cultural relevance. Legacy institutions represent safety, credibility and long-term reliability.
The real challenge for today’s financial institutions is balancing both: adopting the agility and customer-centric innovation of fintechs while preserving the trust and stability that customers expect from established financial brands—and translating that balance into a brand that feels both credible and contemporary across every touchpoint.
Why are challengers so effective at stealing market share?
It’s pretty simple, really – they’re more innovative and much, much quicker to respond to changing customer demands.
Legacy corporations are hampered by their enormous scale, and decades of stagnant processes. Making any minor change at a major bank can feel like steering a cruise ship – turn the wheel and in about an hour the boat will be pointed in the direction you want.
On the other hand you have the challenger banks, who operate less like a classic financial service company and more like the swift-moving tech companies that define places like Silicon Valley. These companies not only are able to offer a highly personalized experience, gorgeous, glitzy branding, and extremely targeted ads, they also leverage performance marketing tactics such as motion design in their ads, user-generated content, and using the channels where their audience hangs out.
The advantage of a better brand
The branding is, of course, a major part of the equation. The FinTech Times even deigned to ask “Is Challenger Bank Success All Down to Branding?” And there’s no denying the bright oranges and pinks that define challenger banks stand out amidst the solemn blues and greys of their legacy competitors. For example, check out this work we did for SALT, a crypto-backed loan company:
But it goes beyond the colour palette – the personalized, more human interaction offered by user-experience-first challenger banks, unhampered by dated core technology is just that much more appealing to the newer generations.
“A more ‘human’ brand identity matters most to digital natives, who have likely never considered a bricks and mortar bank premise as a primary point of contact”
Your business’ brand is a bit like its soul – and people are searching for their proverbial soulmate, for brands who share their values. While large legacy banks have coasted on their air of authority for decades, people are increasingly looking for something, well, a little less cold.
The power of brand-led performance marketing
While “digital marketing” may be used to describe 99% of campaigns these days, the truth is there are individual, nuanced streams of marketing that fast-moving, tech-driven brands are leaning on, often overlooked by the legacy players who still prefer old-school radio and television – channels increasingly less popular among the up-and-coming generations. One of these is performance marketing.
Performance marketing specifically refers to campaigns that only pay service providers after specific, trackable goals have been achieved. A great example of this is Cost Per Click (CPC) ads, where you only pay for clicks on your ad. But performance marketing also drills down to Cost Per Sale (also called affiliate marketing), or scales up to Cost Per Impression (CPM) ads. The idea is that you literally get what you pay for – and you’re paying to engage potential customers.
But it’s not only a channel dilemma, but a messaging one. The most effective brands today aren’t just choosing the right channels—they’re creating ideas that travel across them. Take Ramp, for example. While it’s a B2B fintech brand, its recent Super Bowl and New York OOH campaign didn’t operate like traditional advertising. It tapped directly into pop culture, sparked conversation on platforms like TikTok and extended far beyond the placements themselves. The result wasn’t just visibility—it was participation. Instead of forcing attention through isolated channels, Ramp became part of an ongoing cultural moment.
This is a huge advantage for challengers looking to upset legacy dominance. With leaner budgets, spearfishing becomes more cost-effective than casting a wide net. While tossing up a billboard may have been an effective way to put as many eyeballs on your ad as possible, it was expensive – with no guarantee those eyeballs were attached to people who fit the profile of your customers.
The personalized experience edge
Sign into Netflix, receive 30 movie recommendations based on your preferences. Log on to Spotify, and enjoy a custom playlist designed to delight based on your favourite songs. And Amazon? Expect to be referred to highly specific products customers just like you bought. This is the experience your customers are coming to expect across industries.
Legacy industries, like banking and insurance, are no different. People are increasingly willing to sacrifice the comfort and tradition of the old-school for the custom, personalized, tech-first experience offered by challengers. Whether it’s hybrid bank accounts with special features such as sub accounts or better earn rates because there's no brick and mortar costs, or money saving solutions like auto-budgeting tools, investment round-ups, and zero-fee services. Insurance that is activated as soon as you're done filling out the online form or credit cards that round up your change to invest it and help you budget better, the offers from challenger banks are getting more and more tantalizing.
The role of compliance in leveling the playing field
If speed were the only factor, fintechs would win outright.
But financial services have a built-in equalizer: compliance.
Regulatory requirements slow everyone down—legacy institutions and fintech challengers alike. Legal reviews, risk approvals, data governance, cross-border regulations—these are universal friction points.
Compliance is often framed as a constraint. But the most successful challengers treat it differently.
They:
- Build compliance into workflows early
- Design systems that anticipate regulatory review
- Turn limitations into UX clarity
- Use constraints to sharpen messaging
For legacy institutions, compliance can feel like a brake pedal. For modern fintechs, it’s increasingly becoming part of the engine.
The goal? Shift from seeing compliance as an obstruction to seeing it as a creative opportunity.
When done right, compliance doesn’t dilute creativity—it strengthens it.
Changing legacy mindsets for long-term success
- Ask yourself: “What do our customers want?” And I don’t mean “lower interest rates.” Consider the holistic, human experience. They want content that educates and informs, while being engaging enough to read. They want delightful branding, and a connection to their core values. They want a personalized experience, not a one-size-fits-all solution. For example, a customer who has just started a new job might receive tailored guidance on budgeting, saving and setting up retirement contributions—delivered through in-app tips, short-form content or even personalized email journeys. Someone preparing to buy their first home might see mortgage options framed around their price range, along with educational content that breaks down the process step by step. It’s not just about recommending the right product—it’s about delivering the right message, in the right tone, at the right moment. Ultimately, customers aren’t just choosing financial products. They’re choosing experiences, identities and relationships. And the institutions that understand this—deeply and creatively—are the ones that will earn both attention and loyalty.
- Encourage evangelists. When the experience is incredible, people will want to recommend your business, legacy or otherwise. The thing that makes challenger banks so sexy and easy to refer friends to is the fact that their customers actually believe they made an incredible choice switching their primary account there, and want to spread the love to their community. Foster a mindset where it’s easy to imagine your customers as brand champions.
- Insist on innovation. Without experimentation, your legacy company is going to go the way of the dinosaurs. Unless you want your legacy to be remembered only in business class case-studies of “what went wrong?” you’re going to need to change the way you do business, and pick up the pace. Making smart partnerships (like with Superside) can give you the boost you need to keep pace with leaner challengers.
"Radical innovation requires radical changes in processes, skill sets, technology, culture, and mind-sets—all of which can be daunting and require time, significant investment, and focused commitment."
- Leverage your strengths. The benefit of being a big company is, well, you’re a BIG company! Throw some weight around, leverage a budget that would frighten the average challenger CFO. Internally, you’re going to have to work on shifting the mindset of stakeholders to embrace experimentation and prepare to open the purse strings a bit. But when that mindset does eventually shift, it will allow your legacy company to go toe-to-toe with challengers.
AI governance and the next competitive divide
AI is rapidly becoming the next frontier in financial services—but adoption paths differ.
Legacy financial institutions tend to adopt AI cautiously. Governance, model validation, explainability and regulatory compliance are top priorities. Risk teams need transparency. Legal needs guardrails.
Fintech challengers adopt AI faster—leveraging it for personalization, underwriting, marketing optimization and customer service automation. But even they must implement governance frameworks as regulators sharpen scrutiny.
The future isn’t about who adopts AI first.
It’s about who operationalizes it responsibly.
AI governance—clear policies, documented workflows, human oversight and auditability—will determine which organizations can scale innovation safely.
Creative operations modernization plays a key role here:
- Centralized asset management
- Pre-approved templates
- Modular creative systems
- AI-enabled production workflows with compliance checkpoints
AI without governance creates risk. Governance without innovation creates stagnation.
Winning institutions will combine both.
3 steps legacy companies can take to challenge the challengers
Once you’ve changed your mindset, it’s time to hop in your ship and blast off. Here are 3 to get you challenging the challengers:
- Upgrade your tech stack: The technology your up-start competitors are using is almost certainly more cutting edge than yours. And while it is a bad habit of tech companies to overdo it with hip tools, modernizing your current stack is an essential first step. Take a look at what your challengers are using (we like this site). Subscribe to their newsletters, check out their social media – it becomes pretty obvious the advantage a robust modern tech stack can offer. From a personalized content journey, to accurately targeted advertisements, making a case to modernize can be tough internal conversation to have. But when it comes to evolving or dying, even the most stingy stakeholder can be convinced, especially when it’s a tool the challengers are using to get a leg up.
- Find an opportunity to refresh (or rebrand): This is a big, and probably very expensive ask, that will need to ultimately be decided by committee. But if you’re committed to keeping up with the nimble competitors, it’s a major one you can be a champion of. The best part? You don’t need to pitch this out of the blue. Plenty of big finserves (like Santander) have met with success following a rebrand that went deeper than just a deeper hue of red in their logo. They saw value in a refreshed perception, and have subsequently reaped the benefits – your company can too.
- Make smart partnerships: Hey, if you can’t beat ‘em join ‘em. Plenty of tech companies are partnering with legacy businesses to give them the pep they need to modernize. For finserves, this means looking for a fintech that plugs a gap in their core system, or a design services company (like us!) that can update your brand without blowing up your budget. By working with external partners, you don’t need to build everything in-house, saving internal resources for other projects, and probably decreasing the amount of time it takes to deliver projects. This lets you take a more targeted approach to innovation without attempting to boil the ocean – a much easier sell to relevant decision makers.
How Superside helps legacy brands move at challenger speed
You know those nimble, tech-enabled companies causing waves in your industry? We’re making some waves of our own, elevating the accessibility and quality of design by leveraging global talent.
Whether it’s designing an engaging performance marketing campaign or refreshing your brand to connect more deeply with your customers, Superside works with legacy companies to offer them the design advantages they need to keep pace with challengers.
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