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Have You Considered Online Billing Yet? Ryan Pfleger Tells Us How PayWhirl is Helping Businesses Find Success with Payment Flexibility during The COVID Pandemic

kokou adzo



Ryan Pfleger PayWhirl

First of all, how are you and your family doing in these COVID-19 times?

Ryan Pfleger: We are doing well, it’s been a bit of an adjustment having everyone home at times, but PayWhirl has been a distributed team for the past four years. All our employees work from home, and we use tools like Slack, Pivotal Tracker, Zoom, and GSuite to stay connected. 

Tell us about you, your career, how you founded PayWhirl.

Ryan Pfleger: Our company was founded in December 2013 by Brandon Swift and myself (Ryan Pfleger), but we were developing a different product. Our original product was a website builder similar to Shopify, but with a focus on social commerce. We helped businesses create websites without coding and had several features to help them market their products on social channels like Facebook, Pinterest, etc. As we were developing that product, we kept receiving requests for subscriptions and decided to build an internal app that helped businesses manage recurring payments online. 

We planned to launch it as an app in our website builder’s internal app store but pivoted at the last minute and launched PayWhirl as a stand-alone product. It was one of the best decisions we ever made. Since 2014 we’ve been working on PayWhirl. We have grown from two people in an office the size of a small closet to a team comprised of software engineers, support managers, sales, marketing, accounting, and the other roles you need to operate a business these days. 

It’s been a long road, with many sacrifices, but PayWhirl has grown into a successful SaaS company that helps thousands of businesses manage recurring payments online. 

How does PayWhirl innovate?

Ryan Pfleger: Before PayWhirl, subscriptions were a relatively new concept online. There were tools like PayPal that helped businesses manage recurring payments. Still, they all required extensive development when a company wanted to do anything other than the most basic monthly subscription. PayWhirl’s value proposition is that you can configure it, without coding, to bill or sell to customers, and it covers most use-cases. We support subscriptions, memberships, layaway payments, rentals, pre-orders, and many other billing models. The “do it yourself” entrepreneur of today can go far with the built-in tools we provide, and for developers, the sky is the limit.

Early on, we decided to partner with a few key partners like Stripe, Shopify, and BigCommerce, to reach businesses that needed billing services. We realized that many existing tools were limited and required constant development. Since then, we ended up rebuilding the app back in 2016 and have added many tools to help businesses interconnect with other apps. For example, our webhook engine has been a game-changer and allows companies to connect to thousands of other apps, with very little or no coding. Services like Zapier and IFTTT (If this then that) have made it even easier to manage complicated use-cases. Another focus of ours has been helping businesses automate the fulfillment of their products and services by integrating with order management systems like ShipStation. 

As we’ve grown, we’ve focused more on adding features to make businesses’ lives easier, managing online payments. Admin tools like bulk actions and our payment calendar have helped companies manage their payments effectively. PayWhirl has also utilized a weekly iteration and release schedule since we launched PayWhirl back in 2013. We’re continually listening to customer feedback, developing new features, and releasing changes. The agile development methodology has been a key to our success over the years. It’s easy to stay complacent, but we’re always pushing to make our app as capable as possible.

How the coronavirus pandemic affects your business, and how are you coping?

Ryan Pfleger: I know this is a trying time for most businesses, and while our company has been mostly unaffected by the virus, I know many others are struggling to adapt. 

We’ve been incredibly lucky because our business was nearly 100% digital before the pandemic hit. Our billing software helps businesses manage their payments online and provides tools for their customers to self-manage their accounts. Since the pandemic hit, we’ve seen a relatively large spike because businesses are being forced to consider online billing solutions they wouldn’t have otherwise considered. We’ve helped thousands of companies implement recurring payments since COVID started. 

PayWhirl is very flexible, so we’ve been able to help businesses from all industries adapt to new billing models and manage their payments in creative ways. If anyone reading this needs help with online billing, subscription management, or other billing needs, we’d love to help. 

Did you have to make difficult choices, and what are the lessons learned?

Ryan Pfleger: Fortunately, I haven’t had to make many tough calls, especially compared to other businesses. We did decide to put some development on the back burner and scale our support up a bit to help with the influx of new companies. Overall it’s been mostly positive as we’ve been able to help many brick-and-mortar businesses implement payment solutions. 

How do you deal with stress and anxiety? How do you project yourself and PayWhirl in the future?

Ryan Pfleger: At PayWhirl, we try to focus on being a team. We exchange support requests when someone is frustrated or if a team member is having a bad day. We implemented an unlimited vacation time policy this year, as well, to make sure everyone is getting some time off to decompress from stress associated with COVID and working from home full time. If someone needs time off, they can take it, and the team works to fill in any gaps. While we always strive for excellence, I believe in the saying, “perfection is the enemy of progress,” and I have to remind myself of this from time to time when I am pushing the team. It’s OK to find middle ground sometimes and ease the team’s overall stress, especially in the current environment.

As for the future, right now, we’re focused on mastering our current integrations, rather than adding new partnerships. Focusing on existing relationships has helped reduce stress overall because we’re already familiar with our current partners and can still add value by developing them further. 

An excellent example is our Shopify integration. We’ve been a partner since 2014, and our team knows their platform intimately. Still, it’s been a while since we have made any significant changes to our app, so we’re working on a new app, from scratch, with their team that will enable tons of new functionality. PayWhirl’s new Shopify app will integrate with their native checkout, internal product pages, and more, but it’s not something entirely new for our team. It’s an incremental step in the right direction and has been far less impactful than if we started working on something we had never used. 

Who are your competitors? And how do you plan to stay in the game?

Ryan Pfleger: There are several competitors in our space, but the industry in general, online and recurring payments, has experienced double-digit growth for the past fifteen years. There should be plenty of room for everyone as more and more businesses transition to online billing over the years ahead. We try our best to stay focused on our customers and products rather than worrying about what everyone else is doing. We’ve been around for a while now, so we’ve seen it all. We’ve had competitors copy our software features, market their app with screenshots of our app, undercut our pricing, break rules we follow set by partners, signup under fake names to demo our software, etc. However, if we focused on them, we wouldn’t be helping the businesses who rely on us. In my opinion, it’s always better to focus on what you’re doing rather than your competitors.

Your final thoughts?

Ryan Pfleger: Thanks for the interview and opportunity to share some of what we’ve been working on at PayWhirl. If any of this resonates with you or your business is affected by COVID, we’re happy to help. If you have any questions about online payments, billing, subscriptions, etc. we’ve helped thousands of businesses implement recurring payments and online billing services since the coronavirus hit. We can be reached via our website live chat at or via email at

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Kokou Adzo is the editor and author of He is passionate about business and tech, and brings you the latest Startup news and information. He graduated from university of Siena (Italy) and Rennes (France) in Communications and Political Science with a Master's Degree. He manages the editorial operations at

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