iPMI Global Speaks with Rob Orgel, President and COO, Flywire
- Written by: iPMI Global

In this exclusive iPMI Global interview, Christopher Knight, CEO, iPMI Global, met with Rob Orgel, President and COO at Flywire. They discussed in detail the issues that international health, medical and travel insurance companies face, when collecting global premium payments.
Flywire (Nasdaq: FLYW) is a global payments enablement and software company. Flywire combines its proprietary global payments network, next-gen payments platform and vertical-specific software to deliver the most important and complex payments for clients and their customers.
Please introduce yourself and your background in the payments industry.
I’m the President and Chief Operating Officer of Flywire, a publicly-traded, global payments enablement and software company. We help businesses, institutions and organisations globally simplify the process of accepting complex, high value payments across all of their distribution channels. I lead Flywire’s global payment network, business operations, finance, legal, compliance, and corporate strategy functions. I oversee the business vertical we’ll talk more about here.
I came to Flywire from Apple in 2019, where I was part of the leadership team that developed, launched and grew the Apple Pay business. I was with Apple for 10 years. I joined with its acquisition of Quattro Wireless, which was an early innovator in the mobile advertising space. I have been in the payments industry for more than two decades.
Collecting insurance premium payments across a global customer base isn’t easy. How does Flywire assist the international private medical insurance (iPMI) market?
Flywire isn’t only a payment processor. We also provide the banking network to move the funds globally, and software experiences that make high value transactions appear as simple as making ecommerce ones. Payers see their total policy cost up front, can pay securely in their preferred currency and method, and have confidence their payment went through. Insurers and brokers receive payment in their currency of choice, can track those payments in Flywire’s user interface and see payments data in their system of record if Flywire is integrated.
That solves a lot of issues for the IPMI space – because carriers know exactly when they’ll be paid, how they’ll be paid and what that payment is for.
We’re positioned to serve this market because of our experience with the IPMI industry and our track record in solving these issues for global education institutions and healthcare organisations.
How do international wire transfers, hidden bank fees and high exchange rates present challenges to the international insurance market?
Paying premiums via a manual wire transfer is a massive inconvenience not only for the policyholder, but for the accounts receivable department tracking, receiving and reconciling the payment.
Take a policyholder in Brazil. In order to pay a global health insurance premium that is underwritten in USD, they have to go to their local bank, manually fill out several forms and pay high fees to convert their BRL to the USD Premium, then send those funds internationally. The whole process can take weeks, which for the insurance carrier means delayed payment, and for the policyholder means a time-consuming, poor experience and, worse, potentially being uninsured while abroad. Alternatively, if the individual has a credit or debit card (which is far less common than many may expect), they will pay multiple different fees to the card network and issuing bank on top of what is being charged directly to the insurance company. Foreign transaction and FX fees in particular can mean that the individual is ultimately paying as much as 4-6% on top of what they thought their premium cost would be when they signed up for the policy. All the while, they lack real-time visibility into payment status, which leads to a high number of customer service tickets for the insurer and a less than ideal experience for the member.
Flywire enables businesses to provide local payment options to payers – without taking on FX risk.
What are the other big challenges that international insurers face when dealing with cross-border premium payments?
Two of the biggest reasons global insurers lose customers is that customer payments fail and policies lapse, and the insured seek other, less expensive options. Global insurers often can’t scale to provide expert payment support to customers in their local language and time zones – making it hard to be truly customer-centric in the way the insurance industry is moving. Many companies, including even the most advanced insurance carriers globally, often still rely on manual PDF form fills and phone calls for payment via some distribution channels. On top of that, policyholders generally have to reach out directly to the insurer when there are payment failures and they have questions. The insurer has to check multiple systems in order to find the right information and provide guidance on what to do next. It’s all a lot of back and forth that ultimately results in a poor customer experience, and that can even delay coverage or drive customers to look elsewhere for it.
Can you talk us through how Flywire can modernise legacy payment systems for insurers, without a big-ticket project?
Today’s global insurers find themselves in a tough spot technologically – they’ve either inherited multiple systems through M & A, are collecting payments with different systems in different geographies, and in both cases are weeding through technical debt. On top of that, if an insurance company wants to offer local payment options, they have to have a local entity in-country to offer local card acquiring. They are patching together payment gateways, payment processors and ultimately taking all the risk and responsibility to build this themselves. A true payment partner should remove complexity – not add to it. Flywire integrates with front-end quote to buy systems as well as the CRM and policy administration systems of record through a simple API or existing connectors – ensuring not only that you’re able to maintain a single source of data, but have control over what the payment experience looks like to your users. And we can have all this functionality live within weeks.
How can domestic and international insurers localise and streamline premium collection processes, increase customer retention, and realise significant cost savings?
Providing a way for payers to seamlessly make payments online, in their local currency and payment method of choice – along with conveniences such as support for recurring payments and direct debit – presents a massive opportunity for insurers for both customer acquisition and retention. The best way to tell if you’ve made a quote-to-buy experience easy is when the point of actually making the payment is uneventful for the payer.
The most important part of that is providing users with a familiar solution they trust. Since many payments are made on a recurring schedule, carriers should be incorporating technology such as smart retries, card account updater, tokenization and 3D Secure 2.0 (3DS2) authentication. It is difficult to apply these technologies to all payments when insurers are patching together multiple vendors. This is where Flywire’s turnkey solution really differentiates and solves for the inherent complexities in the IPMI space. One benefit of processing local and domestic payments on the same platform is that insurers can more effectively ensure compliance with global industry standards such as PCI DSS, and regulatory requirements, such as HIPAA.
In a world of compliance, how does Flywire deal with GDPR, HIPAA, and PCI DSS?
Our CTO David King was one of the original architects of PCI DSS – and Flywire now sits on the PCI Board of Advisors, taking a leadership role in shaping the future of payment security. Flywire as a company regularly undergoes the highest levels of security and compliance testing – including SOC 2 Type II. Because of our background in healthcare, education and travel payments, we have always taken very seriously our job to ensure that our clients and their payers can rely on the highest levels of security possible – and are protected against risk.
How complicated is it for insurance companies to integrate Flywire into their premium payment workflows?
Even our most complex clients who have multiple bank accounts across several entities and systems are able to be fully implemented and live within weeks. We pride ourselves on the white-glove level of service we provide throughout implementation and after go-live. Instead of patching together multiple gateways, processors and bank accounts, Flywire gives global insurers a single integrated and embedded solution for all payment types. Instead of needing to build custom fields and different checkout experiences for multiple payment types and workflows, Flywire enables clients to embed all of these options into one single frame through one connection point.
Does Flywire support multiple payment methods, and if so which ones? (Credit cards, debit cards, ACH payments, Apple Pay, Google Pay, Venmo and others.)
Flywire supports 140+ currencies across 240 countries, and multiple payment methods, including cards, online bank transfers, e-wallets, direct debit schemes, alternative payment methods like Boleto, Paypal, and international wire transfers. We are also constantly listening to feedback from our clients and their customers, then incorporating new payment methods into our solution. The key point to note here is that when Flywire does add new payment methods, it does not require any development work on our client’s end, and clients have full control over what payment options they want to offer.