6 days ago
A Fintech Go-To-Market Shift: Preparing For Enterprise Sales
Jayant Walia is Head of Business Development and GTM at Gainbridge, an insurtech revolutionizing the insurance & retirement industry.
At some point in their journey, every ambitious B2B fintech company has to wrestle with this question: Do we keep selling to other tech-forward startups, or do we go after the whales—the banks, insurers and legacy platforms with the biggest budgets and deepest moats?
I've seen this play out countless times. Teams start by selling to fellow builders—fast-moving companies that love APIs, skip SOC 2 on day one and are eager to co-create. Why? Because selling to other startups is faster, cleaner and way more gratifying when you're chasing early momentum and trying to prove something.
But here's the pattern: Those same companies—if they survive long enough—eventually start inching toward banks and large financial institutions. It doesn't happen all at once, but it always happens because that's where the real money is. And that's also when the pain starts.
Why It's Hard To Sell To Legacy Financial Institutions
Banks and large insurers are some of the toughest customers you'll ever chase. They move slowly, scrutinize everything and are not impressed by your slick user interface or recent funding. They've been burned before by outages, compliance failures and integrations gone sideways, and they don't forget.
They also carry tech debt, meaning decades of layered systems patched over rather than rebuilt, making integration risky and complex. When something breaks, it can become a board-level crisis.
But once you're in, you become core infrastructure rather than an experiment. Yet that's the market that keeps so many fintechs up at night—because once you're in, you're in. These aren't transactional customers. You become part of the foundation. You're no longer the experimental layer—you're the infrastructure.
Startups Love Startups (Until They Don't)
It makes total sense that early fintechs target other startups. The sales cycles are shorter. The buyers are more technical. The value proposition is clearer. You can show up with a working demo and close in a few weeks. This approach builds momentum and excites investors. You get to show logos, annual recurring revenue growth and product adoption in a short time.
But there's a ceiling to this model. Your customers are often burning venture capitalist money. Their own stability is shaky. You might spend months onboarding someone just to see them pivot or fold. And before you know it, 80% of your revenue is tied to companies with the same Series B pressure you have.
Enterprise Sales Are A Different Beast
This is where things get real. The shift to selling to banks, insurance carriers or institutional platforms doesn't just require patience. It requires a full reset on how your company operates.
Let's start with the sales team. If your account executives have been closing fast deals with founders and product leads, they're probably not going to enjoy a nine-month sales cycle filled with procurement hurdles, security reviews and six-person buying committees. They may get frustrated or worse, churn.
To avoid this, you need to guide your sales teams into an enterprise mindset. Providing enterprise sales training, bringing in mentors with large financial institution experience and re-evaluating which representatives can adapt to longer cycles are all essential steps. Adding respected advisors or former bank executives further signals credibility and opens doors. As trust builds with large clients, testimonials will naturally follow and accelerate future deals.
Then there is compensation. You cannot keep using a pure SaaS quota system. These deals are whale hunts. You might close one or two a year, but they can transform your business. You'll need to shift incentives toward relationship depth and pipeline quality. You'll need higher base salaries, slower variable payouts and quotas built for fewer but larger wins.
Even your product road map has to mature. It's no longer about just shipping the next feature. It's about proving you won't break under pressure, and that you're scalable, supportable and audit-friendly. It's about proving that you're not just a startup but a strategic partner. You demonstrate this by earning enterprise-level certifications, building real disaster recovery plans, publishing clear uptime commitments and undergoing independent security assessments.
What You Get In Return
Once you successfully reset, it's game-changing:
• Your revenue stabilizes.
• Churn drops dramatically.
• Your margins improve, especially on fee-based models.
• You stop obsessing over month-to-month cash flow swings.
• VCs see a more predictable, defensible business model.
• Most importantly, you're in the room with decision makers who manage billions, not millions.
Now AI Enters The Chat
We're seeing this all over again with the rise of AI in fintech startups. Many are building powerful tools—fraud detection, risk scoring, agent-based onboarding—and again, selling to other startups because it's easier. But we know where this ends: The real opportunity is with the legacy players.
The problem? It's hard to flip the switch later. Selling to large financial institutions isn't an easy pivot; it should be a foundational strategy you bake in early, even if you don't activate it on day one. That means aligning hiring, go-to-market strategy and product development with the long-term vision of serving enterprises so you don't have to scramble for credibility later.
Final Thought
Selling to legacy financial institutions is not for the faint of heart. It's slow, political and demands the long game. But if you want something that survives cycles and builds true enterprise value, it's a move worth making.
Don't wait until you're desperate. The sooner you align your team, your road map and your strategy in that direction, the more likely it is that you'll make it and stay there.
Opinions expressed here belong solely to the author and do not necessarily reflect the views of their employer.
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