Attending Money 20/20 Las Vegas this year validated an important hypothesis: onboarding remains one of the greatest challenges for fintech, especially within the payments and B2B space. The event brought together a vibrant mix of founders, investors, product leads, and innovators, all united by a shared goal to enhance fintech workflows and customer experience.

Fintech Onboarding: The Hidden Bottleneck

The conference reconfirmed that inefficient onboarding workflows are still a significant pain point for major payment platforms. Despite massive growth and scale, many platforms onboarding thousands of merchants still wrestle with complex, manual migration processes that slow down go-lives and frustrate customers. Through deep-dive conversations and follow-ups with product owners, it became obvious that automation and intelligent workflow design in onboarding can fundamentally change how quickly and smoothly these platforms move merchants from legacy processors.

With the right approach, there’s a clear path to both operational efficiency and higher satisfaction scores.

Money 20/20 spotlighted how solving this onboarding problem at scale can unlock value for all players in the ecosystem: platforms, merchants, partners, and investors alike. The push to improve this area isn’t simply incremental, it’s a potential game-changer that can drive widespread adoption and deepen relationships up and down the payments stack.

Integrations & Customization: Less Hype, Real Value

Another ongoing trend is the demand for seamless integrations. While custom integrations will always be necessary as platforms expand into new markets and verticals, the most transformative wins right now are being driven by smarter onboarding flows rather than integration alone. This subtle shift in focus stood out during founder roundtables and in talks with product and engineering leaders at the show.

From Investor Conversations to Founders’ Insights

Money 20/20 isn’t just a gathering of industry titans, it’s also an unmatched opportunity for genuine dialogue. From roundtables organized by leading venture firms to lively breakfasts and serendipitous hallway chats, the event delivered a wealth of perspective on the challenges, opportunities, and emerging trends in fintech innovation. High-caliber investor interest and the ability to connect with other founders proved invaluable for exchanging ideas on customer acquisition, funding, and international go-to-market strategies.

Wrapping Up: Momentum, and Opportunity

Beyond the sessions and networking, the diversity of experiences—from PR shoots to offsite breakfasts, made Money 20/20 Las Vegas a powerhouse for inspiration and action. The conference underscored the urgency and opportunity in reimagining fintech onboarding, confirmed market appetite for automated solutions, and fostered connections that will fuel meaningful change in the months ahead.

As LINK continues to push the boundaries of onboarding automation and merchant migration, the event reaffirmed our commitment to solving these challenges at scale and collaborating with industry leaders driving the next wave of fintech innovation.

Whether you’re a fintech founder, investor, or payments innovator, the key takeaway from Money 20/20 is clear: the future will be shaped by those who simplify onboarding and migration, making it as seamless and scalable as the products themselves.

Building a startup isn’t a straight line. It’s a series of experiments, pivots, and bets—some that work, and some that teach you the hard way.

Over the last few years of building Link, I’ve learned that success isn’t just about having a great product. It’s about how you sell it, how you keep innovating, and how you choose to fund your journey.

Here are three lessons that have shaped the way I run Link and that might spark ideas for your own entrepreneurial path.

1. Sales and marketing: Find the most efficient path to market

As a tech entrepreneur, pushing the boundaries on product innovation is key. But it’s equally important to be nimble with sales and marketing.

When we started, we sold directly to merchants—retailers and restaurants. Selling and scaling into this segment is challenging due to its fragmentation. You either need deep venture capital pockets or an incredibly efficient way to reach them.

That efficiency came when we discovered a better route: selling through the tech platforms that already serve these merchants. Instead of building a large sales team, we made the platforms and their sales teams our customers. They, in turn, connect us to their merchants, our end users.

Once we validated this model with one point-of-sale system, one accounting platform, and so on, scaling became much faster. We now work with multiple platforms across retail and food, and their channels effectively serve as our sales force while LINK delivers value for both the platform and the merchant.

Takeaway: Look for distribution channels where someone else already has the audience you want. It can be the difference between slow, expensive growth and fast, scalable traction.

2. Innovation: Keep research alive while serving your core

Every startup wrestles with the same challenge: how do you push into new ideas without losing focus on your bread and butter?

AI is the latest wave where this question comes up. LLMs and agent-centric models are everywhere in the conversation, but figuring out how to actually use them meaningfully is another matter.

At LINK, accurate and dynamic mapping between systems is mission-critical. So we put two engineers into “lab mode” for months to hammer away at LLM capabilities. Eventually, they cracked it. When we demoed the solution to one of the largest point-of-sale and payment companies in North America, they immediately saw the value. We’re now taking it through the next stages of market rollout.

Takeaway: Even when it’s hard to justify in the short term, consistent R&D pays off. Your prospects and customers are exploring these same technologies—if you’re not, you risk becoming irrelevant.

3. Funding: Take only what you need; keep control where it counts

“How much should I raise?” is a question every founder faces. One thing I’ve learned is that it’s not just about the number—it’s about control and flexibility.

It’s tempting to think you need to raise $50M or more to have a shot at a billion-dollar exit. But in many cases, you might only need $7M to reach profitability and still execute well beyond that. That can often be done with angels and smaller funds, without giving up too much board control or company rights.

Why does this matter? Markets fluctuate, obstacles arise, and founders require the ability to make flexible decisions. Once you give that away, it’s difficult to get it back.

Takeaway: Raise in smaller chunks, choose your investors carefully, and keep the door open for future funding by nurturing long-term relationships.

What is iPaaS?

iPaaS is a cloud-based integration solution that helps businesses connect all their applications, data, and services without needing complex coding. Think of iPaaS as a bridge that allows different systems to “talk” to each other and share data automatically.

The best part? iPaaS comes with prebuilt connectors and ready-to-use templates. This means instead of building integrations from scratch, your IT team can quickly set up connections using a simple, user-friendly interface.

How does iPaaS work?

Imagine this scenario. You use Salesforce to manage customer relationships and QuickBooks for accounting. Without integration, your team would need to manually transfer customer and order details between these two systems, which is time-consuming and prone to errors.

With iPaaS, you can connect Salesforce and QuickBooks in minutes. The data flows seamlessly between the two platforms without any extra work.

But iPaaS doesn’t just connect apps. It also takes care of:

• Data mapping and transformation: so information is formatted correctly between systems.
• Workflow automation to manage processes that involve multiple apps.
• Monitoring and alerts :so you know your integrations are running smoothly.

Why should businesses care about iPaaS?

iPaaS offers much more than convenience. It brings real, measurable benefits.

It saves time. Your developers no longer need to write endless lines of code to keep systems in sync.

It ensures real-time data sync. Updates happen instantly across all connected platforms, reducing mistakes and delays.

It grows with you. As your business adds new tools, iPaaS makes it simple to expand integrations without starting from scratch.

It cuts costs. By automating workflows and reducing manual tasks, iPaaS helps teams work smarter, not harder.

The bottom line

If you’re still relying on manual processes to move data between your systems, it’s time to rethink your approach. iPaaS eliminates integration headaches by enabling real-time connectivity and automation, which means fewer errors, faster workflows, and happier teams.

As businesses continue to adopt more cloud applications, having a reliable integration platform is no longer optional. Whether you’re a growing startup or a large enterprise, iPaaS can be the solution that connects all your tools and data in one seamless flow.

Ready to explore iPaaS solutions? Start by identifying the apps you already use and where data silos are slowing you down. From there, look for an iPaaS platform that offers the right connectors, automation features, and scalability.

Not all POS systems are created equal

The system that works for a small boutique may not suit a bustling café, and a multi-location retail chain will have different needs entirely.
For example:

• A cloud-based, no-frills POS might work perfectly for a small pop-up store.
• A full-featured system with advanced inventory tracking and reporting could be essential for a growing restaurant group.

6 tips for finding the perfect POS for your business

1. Define your must-have features – Make a checklist. Do you need mobile payments? Inventory management? Loyalty programs? Decide what’s essential before you start shopping.

2. Look at all the costs – Hosted (cloud) systems may be cheaper upfront compared to installed setups, but check for monthly fees. Add in hardware costs, too.

3. Check integrations – Your POS should sync smoothly with your accounting, CRM, and e-commerce tools.

4. Pick a vendor with great support – Even the best POS will have hiccups. Reliable, responsive customer service is a must.

5. Do your research – Don’t rely solely on the sales pitch. Read online reviews from real users.

6. Test before you commit – Many POS providers offer free trials. Use them to see if the system actually works for your business.

Your POS is the foundation for growth

The right system will help you manage sales, inventory, and reporting with ease, giving you a platform to grow your business.

Have any tips of your own for choosing a POS? Share them in the comments!