Payments can make or break a business, especially for fast-growing startups where every transaction counts. From optimizing conversion rates to managing risk, payments aren’t just a back-office function, they directly impact revenue, customer experience, and expansion opportunities.
To explore the most pressing payment challenges startups face, we sat down with Gianluca Cassaro, VP of Revenue at Simple.Life, an app that helps clients lose weight and improve their health through its award-winning AI coach and personalized plans.
Gianluca brings deep expertise in payments, having previously built and scaled payment systems at Palta, Badoo, and Bumble. His experience spans everything from optimizing recurring payments to expanding into new markets while balancing fraud prevention and conversion.
Find out how 150 high-growth businesses are navigating payment challenges and how the smartest startups are starting to treat payments not as plumbing, but as a lever for growth. Get the report.
Interview
What are the most significant payment challenges fast-growing startups typically face in their early stages?
In the early stages, startups encounter several payment-related challenges, many of which can have long-term consequences if not addressed properly.
One of the most significant issues is understanding the initial investment in people and skill sets. Deciding which teams should be responsible for payments—whether product, operations, analytics, or engineering—can be tricky. These first people working on payments often shape the foundation for future decisions, and if they make the wrong choices, startups can end up with a legacy system that’s difficult to change later on.
Another key challenge is maximizing conversion. This isn’t just about improving acceptance rates, but also about ensuring that as many customers as possible successfully complete the payment process. Many startups focus solely on payment acceptance rates without considering the broader picture. Optimizing the entire funnel can make a massive difference in revenue.
The ability to experiment and pivot quickly is also crucial. Many startups evolve their monetization models as they grow, but rigid payment setups can slow them down. Whether they’re transitioning from a one-time purchase model to subscriptions, introducing new payment methods, or expanding into new markets, they require a payment infrastructure that enables flexibility.
Managing risk is another often overlooked challenge. Many early-stage companies don’t fully grasp the complexities of fraud and chargebacks until they become a significant issue. If left unchecked, fraud can lead to substantial financial losses, reputational damage, and even restrictions on payment providers.
Finally, payments don’t operate in a silo; they overlap with many different teams, including finance, product, customer support, marketing, analytics, engineering, and compliance. Navigating these cross-functional complexities can be difficult, especially as startups scale.
Payments must be seen as a strategic function, not just an operational one, to ensure smooth collaboration across departments.
At what point do payments become a blocker for growth, and what are the warning signs?
Payments become a blocker for growth when they negatively impact customer experience, operational efficiency, or expansion efforts.
One of the most apparent warning signs is a poor customer payment experience: high cart abandonment at checkout, increasing failed transactions, and declining renewal rates often indicate friction in the payment process.
Security and compliance risks also pose significant threats, as rising chargeback rates, negative reviews citing fraud concerns, or failure to meet regulatory standards can damage a company’s reputation and lead to financial penalties.
Operational inefficiencies are another red flag. It diverts focus from growth initiatives if finance teams are bogged down with manual payment reconciliations, financial reporting delays, or a growing backlog of unresolved payment issues.
Startups also often underestimate the extent to which their payment setup will need to evolve as they scale. A common mistake is choosing a payment provider based solely on immediate needs without considering long-term flexibility and scalability.
Delays in launching new features, difficulty integrating payments with key business tools, or inconsistent reporting data are strong indicators that payments act as a constraint rather than an enabler.
How should startups balance the need for quick market entry with long-term payment scalability?
The payment experience is a critical part of the overall customer journey; it can make or break a company. When launching quickly, startups must ensure that the payment system isn’t just a temporary fix but a robust foundation for future growth.
My approach is first to identify the key business-critical components from day one. These core elements should be non-negotiable and must align with a long-term vision of evolving the payment capabilities over time. For example, avoiding vendor lock-in is essential so that you aren’t constrained as your business scales or shifts into new markets.
Other critical elements are ensuring checkout form flexibility and seamless integration with your broader tech stack. These features allow you to adapt to changing customer expectations, introduce new payment methods, or integrate additional functionality without needing a complete overhaul.
Ultimately, balancing quick entry with long-term scalability is about identifying and investing in the non-negotiable elements that guarantee a smooth payment experience. This strategic focus allows startups to capture market share rapidly while building a payments infrastructure that supports sustainable growth over time.
What factors do you consider when deciding between a single payment provider and a multi-provider strategy?
This is a no-brainer. Why would you put all your eggs in one basket, all your gold in a single safe, or all your investments in a single stock? The same logic applies to payments.
Relying on just one provider exposes a business to operational, financial, and strategic risks. You're at risk if the provider experiences an outage, changes its pricing, or stops supporting a key market. A multi-provider approach ensures redundancy, better cost control, and improved performance through optimized payment routing.
That said, the transition to multiple providers should be planned carefully. Businesses must ensure their infrastructure supports multiple integrations without introducing unnecessary complexity. The goal isn’t just to have various providers but to have a setup that allows for seamless switching, cost efficiency, and adaptability as the business scales.
What are the key signals that indicate it’s time for a startup to invest in optimizing its payment infrastructure?
Payments are crucial to your company's success when customers arrive at your checkout and express interest in your product. Payments directly impact key economic metrics, such as Return on Ad Spend (ROAS), Average Revenue Per User (ARPU), and Customer Lifetime Value (LTV). If your payment setup isn’t optimized, you leave money on the table.
What metrics should startups use to calculate the ROI of improving payments—what metrics matter most?
The right metrics depend on the industry, monetization model, and margins; however, there are key commonalities that every startup should track. Payments directly influence conversion, revenue, and risk management, so measuring ROI means examining how well payments enable business growth rather than restricting it.
Payments set the ceiling for a company’s revenue potential. If a business can generate $100 million but has a flawed payment system, it might only capture $50 million, or even less. The cost of running the payment architecture, as well as the risks of fraud or non-compliance, further impact the bottom line.
Ultimately, payments should be seen as a strategic investment, not just a cost center. Leadership teams and boards require individuals who can analyze and effectively communicate the impact of payments on growth, profitability, and expansion, ensuring the optimal level of investment in payment infrastructure.
Why should businesses consider using something like Primer? How can payment optimization impact revenue, customer experience, operational efficiency, and expansion opportunities?
In my previous roles at global companies, we built and managed most of our payment stack in-house. While this approach worked at scale, it required a massive investment, which is not realistic for a startup or mid-sized company. What makes sense for a giant like Microsoft could be a terrible investment for a growing business.
When we built our payments strategy, we mapped out:
- The payment capabilities we needed from the very beginning.
- The capabilities we’d need in the near future, based on our growth plans.
- Which of these required an in-house investment, and which needed a partner?
For most of the capabilities that required a partner, we chose Primer.
Primer is a flexible, enterprise-grade platform that meets our current needs, enabling us to scale efficiently without requiring extensive internal development. It provides access to a wide range of payment services through a single API integration, making it easy to add and switch providers as needed.
Beyond integrations, Primer’s workflow automation enables us to optimize conversions and minimize friction without requiring complex engineering work. We can:
- Establish rules for different transaction types (customer-initiated vs. merchant-initiated) to enhance authorization rates.
- Manage risk by blocking high-risk transactions based on markets or BINs.
- Automate key optimizations, such as Adaptive 3DS, Fallbacks, and Network Tokenization, to further enhance payment performance.
Since using Primer, we’ve realized:
- Higher revenue: More successful transactions result in higher authorization rates and reduced revenue loss due to failed payments.
- Better customer experience: Frictionless checkout and intelligent authentication improve conversion and retention.
- Greater operational efficiency: Automation and smart routing reduce manual work for payment teams.
- Easier expansion: With Primer, we can quickly enable new payment methods and markets without requiring infrastructure overhauls.
In addition to all this, Primer’s analytics suite provides in-depth insights into payment performance, enabling us to continually refine our approach. The combination of flexibility, automation, and optimization makes Primer a strategic partner that allows us to focus on growth without being hindered by payment complexity.
What to learn more about what Primer can do for you? Get in touch.
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