Technical.ly is a free news resource thanks to financial supporters like Perpay, a Technical.ly client, which sponsored this article. It was reviewed before publication. Learn more about Perpay.
When Perpay first launched in 2017, every team member and every department at the Philadelphia-based fintech firm participated in customer support. That drove insights that informed product ideas and marketing, with new hires rapidly scaling into new roles as the company grew.
Job titles were fluid, but one throughline emerged: Team members accelerated their development by interacting directly with the customer and engaging with different departments.
“[The pattern] existed informally almost since the beginning of the company,” said senior director of operations Michael Kassak, one of Perpay’s early hires and early leaders. “I came in, I did customer service, wore a lot of hats, learned about what the business did and my curiosity and desire to have an impact led me through a variety of roles and departments.”
What began as an “all hands on deck” necessity in a fast-paced startup quickly evolved into a competitive advantage and unparalleled internal career development program. As Perpay, one of Philadelphia’s fastest-growing companies, continues to rapidly scale and evolve, the once-informal approach has become a formal rotational program, and in turn has become a foundational tenet of the company’s approach to talent and culture.
“We have an unlimited appetite for wanting to grow the company with internal, young, hungry talent versus having to go and externally hire,” Kassak said.
From ad hoc practice to a structured program
The formal program was a solution to a good problem: growth. A few years in, the demand for cross-functional support had multiplied significantly.
The company decided to build a more intentional structure: new team members would spend their first quarter in Business Operations, grounding themselves in customer needs, workflows and product behaviors. After that, they’d complete 10-week rotations with teams across Product, Marketing, Merchandising, Compliance, Acquisition, Credit Card and more.
“We have about six or seven teams that always participate quarterly,” Kassak said, “and team members dedicate roughly a third to half of their time each quarter working with that team.”
Each rotation combines “always-on” work, such as supporting team workflows or responding to operational insights, with an impactful project where the team member can meaningfully contribute. Team members are encouraged to “be curious” and pursue interests that allow them to discover their ideal trajectory with each rotation.
For early-career hires, it’s a chance to learn about how to be a part of a workplace and find a role where they can maximize their impact.
“It really is a promote-from-within mindset,” said Kylie Young, Perpay’s customer acquisition manager, who started as an intern in 2019. “I can’t underscore the opportunity enough.”
In her first year, Young was engaging with senior-level leaders across several departments, experiences that helped her understand not just what she could do, but what she wanted to do.
“In a year’s time, I was navigating conversations with some of our most important partners and that responsibility helped me realize that this is what I actually want to focus on,” she said.
Learning by doing
Titus Clark, who joined Perpay in 2024 as a recent graduate, said the rotation experience was one of the main reasons he wanted to work there. He was initially drawn to the company’s mission of providing accessible financial products and wanted to be in a role where he had the ability to contribute in a meaningful way.
“Being able to make an impact fresh out of college really drew me to the program,” Clark said.
The Operations-first approach grounds team members in customer needs and gives an immediate window into how Perpay works. “There’s really no better way to learn about the product than hearing all the customers’ questions,” said Kyle Castagna, who joined in 2022 and now serves as a product manager.
By the time team members begin rotating, they already understand customer needs in a way many product or marketing hires don’t encounter until years into their careers. That context shapes and maximizes the impact they are able to have across the rest of their rotation assignments.
For Clark, that meant blending his newfound understanding of the customer experience with his interest in product design. “I had the opportunity to help with the redesign of our e-commerce storefront and product widgets,” he said, a hands-on design project that gave him visibility into workflows across Product, Design and Engineering.
Castagna had a similar experience during his credit card rotation. “One big project I worked on was our credit line increase program,” he said. “That was a major responsibility and I could see that it had a direct impact on our customers’ purchasing power.”
Even with a more structured program, each team member’s journey is unique. “One of our core values is being curious, so I really tried to carry that with me,” Clark said. “You weren’t pigeonholed into one specific area. I loved having the opportunity of choice.” The program is designed to give both the team member and the individual departments the opportunity to find alignment between passion, skill, and the needs of the company.
By the time Castagna joined the Product team full-time, he wasn’t a novice. “I was already the subject matter expert,” he said, a direct result of time spent in Operations and rotations that served as an accelerated master class in the credit card industry.
After rotations in Product, Design and Merchandising, Clark assumed he’d pursue a product role. But something pulled him back toward a leadership role within Operations.
“It wasn’t intentional, I actually wanted to join Product after my rotation,” he said. “But I saw an opportunity to bridge the gap between Operations and Product that could improve the customer experience.”
He worked with leadership to carve out a new position that blended his passion, skill set, and ability to maximize impact. “I was able to curate a role for myself, which is super unique.” Today, that role has become a crucial connector between teams. The hybrid position he once imagined has grown into a foundational part of how teams collaborate with Operations.
Accelerated context building
“Every department speaks a different language,” Clark said. “Doing rotations lets you learn how to communicate with each team.”
That familiarity accelerates cross-functional work, especially as team members grow into leadership roles.
“All the time, I’m working on projects where the lead is someone who used to be in Operations,” Kassak said. “They understand the full life-cycle of the product and how it connects to the customer experience intricately.”
Young, who now manages Perpay’s customer acquisition strategy, said that cross-functional experience helps early-career team members determine their direction.
Perpay’s in-person culture acts as an accelerant to building important institutional knowledge.
“Being five days a week in person is honestly a game changer,” Clark said. “Our collaboration and ability to be in constant proximity are invaluable. This continuous exposure helps early-career team members gain a deeper understanding of the entire organization and the network of people at their disposal.”
Growth fueling growth
To support Perpay’s rapid growth, the team is super-sizing recruitment efforts through Super Day, an accelerated, invite-only hiring event on January 7, 2026 at the company’s Center City headquarters.
“We’re looking to find and hire as many top entry-level candidates as we can,” Kassak said. “If you are aligned with our mission, and demonstrate the ability to scale, there’s no better program in the country for accelerating early in your career and making an impact.”
Super Day is intended to give candidates a fast, in-depth look at Perpay’s team and culture, and for the company to quickly identify great fits.
“Our commitment is to give qualified candidates an offer within 48 hours,” Kassak said.
Perpay’s Business Operations Rotational Program has quietly established itself as a unique and effective career launchpad that is building the foundation for the company’s future growth.
