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Fragmented customer journeys and rising expectations for personalization… A fintech marketer with the right kind of eyes will recognize these signals as a call for a more intentional approach.
In our recent conversation, Upside VP of Growth Rob Giannone suggests that modern fintech growth is based in smarter, more precise marketing that combines product, data, and experience into something that actually resonates.
Personalization is the foundation
There was a time when basic segmentation felt pretty sophisticated. Marketers could create a few broad audience personas, set up some basic lifecycle email flows, and maybe layer in simple behavioral triggers. Now, customers aren’t satisfied with being relegated to a bucket.
“Honestly, anything that isn’t hyper-personalized just doesn’t work anymore. The old ‘batch and blast’ or linear lifecycle journeys feel outdated when consumers expect experiences tailored to their exact needs.”
At Upside, personalization is embedded in the product itself. Their dynamic offers engine adjusts based on who a user is, where they are, and what’s available around them.
“Our biggest opportunity lies in orchestrating these hyper-personalized journeys across lifecycle channels, like email, push, in-app, and others, to ensure we’re always delivering the right message to the right person at the right time. That’s the new growth playbook.”
Personalization can’t live in silos. It has to be orchestrated across the entire journey, from acquisition to retention to reactivation. Anything less feels generic. And generic is how you get ignored.
AI powering scale and relevance
If hyper-personalization is the goal, AI is really the only way to achieve it at scale. But what’s notable in Upside’s approach is how practical and immediate the applications actually are.
“Right now, we’re leaning into AI primarily for content creation, which lets us produce high-quality assets efficiently and at scale,” says Rob. “We already have fully AI-generated radio and TV spots live in market, and we’re expanding into static and video creative next. On the lifecycle side, AI is helping us automate optimization, like subject lines, preview text, and creative elements that continuously self-test and improve without manual A/B work.”
This represents a big shift away from tedium and toward strategy. AI can generate, test, and refine faster than any team. But it still needs reliable guidance. The brands that win will be the ones that pair AI-driven execution with human-led insight.
“It’s about delivering the right message, offer, and incentive to the right person at the right time,” says Rob. “Which is something that’s nearly impossible to do at scale without AI.”
For more insight and a strategic approach to implementing AI in your creative, check out this marketer’s guide to the teen years of generative AI.
Clarity over innovation
Fintech adoption usually doesn’t fail because of a lack of interest. It fails because of friction. Users download the app. They poke around. And then… nothing clicks. Nothing sticks.
Upside’s strategy is to compress the time between download and value. That first experience needs to be functional, as well as emotional. This is where clarity of application becomes a growth lever.
“The faster we can get someone to that first cash-back moment, the better. It’s really about building trust early,” says Rob. “People want to know, ‘Is this real, and how does it work?’ The key is communicating clearly and quickly how it works and where the cash-back comes from.”
Too often, fintech brands overcomplicate their messaging in an effort to sound innovative. But innovation without clarity creates hesitation. And that hesitation can kill your momentum. The brands that win are the ones that make value (and how that value applies to the user’s daily life) immediately obvious.
“Once users see that first couple of dollars appear, the value clicks instantly.”
Habit formation is built on relevance
Getting users in the door is one challenge. Getting them to stay is another. Upside’s approach focuses on embedding the app into real-world behavior.
“Resonance, resonance, resonance, repeats Rob. “Resonance is everything. We’re working to make the app part of users’ everyday rhythm by connecting offers to real-life triggers. Things like local events, traffic, or even weather.”
Most lifecycle marketing relies on scheduled touchpoints (e.g., weekly emails, monthly nudges, generic reminders, etc.). But users don’t live their lives on marketing schedules. They respond to context. FInding that relevant content can be the difference between being another annoying notification and becoming part of a user’s routine.
“It’s about relevance, not noise. Timely, helpful nudges instead of generic reminders.”
Community as a growth channel
Trust is everything in fintech. Performance marketing can only take you so far.
That’s where community comes in.
“Word of mouth is everything,” says Rob. “People trust people they know.”
Upside is leaning into this through referrals, but also by expanding the concept into something bigger.
“We want to build a real sense of community through loyalty elements, like gamification, leaderboards, and groups that make sharing feel natural and fun,” Rob explains. “There’s real power in creators authentically sharing how the app fits into their lives, sharing tips like stacking rewards and detailing smarter saving habits in their own voice. Those stories resonate more deeply than brand messages alone.”
This reflects a broader shift in fintech marketing. Authority is built jointly by brands and networks of users, creators, and communities. If your growth strategy doesn’t include social proof, it’s just incomplete.
Check out why human influence still matters in the age of AI to see how you can empower your most passionate storytellers.
Reactivation is like a second first impression
Dormant users aren’t lost; they’ve just become disconnected. And the way you bring them back matters. A traditional reactivation campaign reminds users of what they already know. A re-onboarding experience shows them what’s new and why it matters now.
“We treat it less like a simple ‘win-back’ and more like a re-onboarding,” says Rob. “If someone hasn’t used the app in six months, a lot may have changed. There could be new merchants in their area, new offers, or new ways to earn. So, we focus on meeting them where they are and showing what’s new and relevant in their area. ”
This reframes reactivation as an opportunity to recover users by reintroducing the product in a more compelling, and more personalized way than before.
Product and marketing are not separate
Modern fintech growth requires breaking down traditional silos between teams. Marketing should not operate solely as an acquisition engine, and product should not be viewed as just the owner of the user experience. Instead, growth is most effective when these teams work together, aligning on shared goals and collaborating across the entire customer journey.
“User experience and design are everything for us. It’s what makes us stick,” says Rob. “We’re a product-led company at our core, and the strength of our app experience drives both engagement and retention. Marketing and product work hand in hand on this, constantly testing and optimizing the journey to reduce friction and guide users toward that first rewarding moment.”
When teams closely collaborate around the customer experience, the result is a more cohesive and intuitive product that users can easily trust and incorporate into their daily lives. Every interaction should reinforce value, drive engagement, and improve retention.
Sometimes growth comes from unexpected channels
In an industry obsessed with the next big thing, there’s still something to be said about keeping it traditional. A lot of brands will dismiss legacy channels, while others embrace them.
“One counterintuitive lesson has been the power of ‘old school’ channels like linear radio,” says Rob. “It’s become surprisingly CAC-efficient, even though radio hasn’t historically been a go-to in tech or app marketing. It’s a historically awareness-centric channel that’s turned into a real growth driver for us, proving that sometimes the channels everyone else abandons still work if you invest thoughtfully. Don’t just chase what’s trendy. Look for opportunities where others aren’t playing.”
The importance of clarity
Clarity in messaging. Clarity in value. Clarity in experience. It’s what accelerates that first moment of trust. It’s what makes personalization feel helpful instead of invasive. It’s what turns engagement into habit.
And when fintech options are endless and attention is limited, clarity becomes a competitive advantage. Because when users understand exactly what they’re getting (and why it matters) they convert. And stick.
Are your growth strategies built for how customers engage today, or are they still anchored in how marketing used to work? Let’s talk.
