Every five years, Brad Oddo sends an employee away. The destination is theirs to choose. Basys pays for the vacation and adds an extra week of leave that year. When the employee returns, Oddo wants to see the photographs. For a founder whose business involves moving other people’s money, this is a particularly agreeable transaction: a company buys a trip, a colleague brings back a memory.
He described the arrangement at a Kansas City small-business panel in 2023. His delight was in getting to share a little of the experience afterward. A retention benefit had become something people could point to, rather than another paragraph in an employee handbook. The photograph of a holiday has an advantage over a mission statement. Someone actually had to go somewhere.
Oddo founded the payments company Basys in 2002. His working life has since encompassed software, bank partnerships, apartment development and community service. Yet the vacation story offers a useful entrance to his thinking. He keeps returning to a practical question: what would make someone want to stay?
A lesson learned before the first sales call
One answer began with his father. As a middle-schooler accompanying him at work in building services, Oddo noticed the way he spoke to people. Employees received the same respect as the company president. Rank changed the job, but it did not change the courtesy. His father and grandfather supplied an example of work that he wanted to live up to.
His first sales job was working for his father. The routine involved 40 cold calls before lunch and another 40 afterward. That is a considerable number of opportunities to become less precious about rejection. It also taught him to enjoy meeting people. Years later, in a business full of technical language, the elementary act of starting a conversation would remain central to his account of how things get done.
His education took a detour. He left the University of Kansas three credit hours short of a degree, then returned years later to complete it. The diploma went into a black-and-gold frame, a concession to a childhood allegiance to Missouri. Academic closure, apparently, did not require surrendering the family colors.
“Everyone deserves to be treated with respect.”
Brad Oddo
He eventually put his business intentions into a 23-page plan. Taking care of employees and clients was part of the founding proposition. The interesting thing about that order of priorities is the obligation it creates. A founder can write whatever he likes in a notebook. The people who join him will discover whether the cover bears any resemblance to the contents.
Five people, one copier, plenty of applications
The early Basys office was small enough for everyone to do a little of everything. Long-serving colleagues Kim and Karen recalled a five-person operation, a copy machine and a large table covered with applications. They answered calls, brought merchants aboard and processed paperwork. There was no great distance between the people making promises and the people expected to keep them.
Their recollection contains a detail more revealing than the furniture: merchants became familiar by voice. People sometimes called simply to check in. For a payment processor, that familiarity was a commercial asset. A customer did not have to become a fresh case each time the telephone rang. Someone already understood the business on the other end.
By Basys’s March 2025 anniversary, Kim and Karen had been there for 20 years, having started on the same day. The company said it had doubled in size over the preceding three years. Those two timescales make an instructive pair. Growth brings new names to learn. Long service preserves the memory of why the old habits mattered.
Oddo’s company would go on to win a 2024 Excellence in Customer Service award from Business Intelligence Group. Basys also appeared at number 4,802 on the 2024 Inc. 5000. Such recognition records a moment. Keeping someone who remembers the application-covered table is a different sort of evidence: the organization has grown around people who can still remember its beginnings.
Coach Oddo has a hiring policy
Oddo prefers “coach” to CEO. His explanation is about shared outcomes: the coach’s result depends on the team’s result. He also describes a “no jerks” policy. It is a compact piece of organizational language, with rather less room for interpretation than the average corporate values poster. Different talents and temperaments are welcome; mutual respect is expected.
There is a temptation to hear that language as the easy optimism of a founder who enjoys his colleagues. He does seem to enjoy them. But the preference also establishes a standard for his own job. Coaching requires attention to other people’s performance, rather than merely having an impressive title while they work.
The emphasis has followed him into public conversations. In 2025, podcast host Alana Muller described her longtime friend’s disposition as upbeat and positive. Their conversation concerned culture and employee retention. Her familiarity with him gives the observation a personal scale: this was someone she knew, talking about the way he wanted other people to experience their working days.
The sales lesson gets another classroom
For someone whose own introduction to sales involved a formidable quota of cold calls, helping students enter the profession makes sense. Basys supported Kansas State University’s National Strategic Selling Institute and named a room in its office. In 2023-24, Oddo described the partnership in terms of future sales leaders and career opportunities for students.
The photographs offer a welcome interruption to the language of corporate partnerships. There is a group seated together, and another picture with sunglasses and hand gestures. The occasion is formal enough to name a room, informal enough for people to enjoy being in it. A relationship with a university also asks a company to explain its work to people who have yet to choose an employer.
Oddo did eventually finish his own degree. Here, the connection runs in the other direction: an established founder offering students access to a working business. For a young salesperson, the chance to see what happens after the sale can be as useful as learning how to make one.
A payments company learns to make the tools
Customer service becomes more consequential when a company builds more of the machinery customers use. A 2021 partnership with AACRO Computer Systems brought Basys payment collection to Print Shop Manager users. Estimating, accounting, invoicing and collecting could sit within a connected workflow. The practical appeal was straightforward: the printer had work to finish without giving payment administration a separate career.
That same year, City Wide Facility Solutions announced a partnership giving its clients access to Basys’s proprietary iQ Pro solution. Oddo’s public comments emphasized the service relationship. Across these arrangements, his audience was often another organization that would be putting its own reputation beside Basys’s work.
In September 2025, he joined Jim Marous on Banking Transformed to discuss merchant services and business banking loyalty. The episode, sponsored by Basys, concerned the opportunity for banks to build commercial relationships through payments. That is an important change of perspective for understanding his work. A processor helps collect a payment; a bank partner also has to consider what the merchant remembers about the experience.
By February 2026, Basys was announcing a QuickBooks integration through iQ Pro+, supporting both Online and Desktop users. Payment links could be placed directly in invoices. The company’s stated aim was to reduce the manual work around getting paid. Oddo’s concern, as he expressed it, was that business owners should be able to collect money inside tools they already used.
On October 13, 2026, Basys announced another iQ Pro+ release, bringing invoicing, recurring billing, customer management and payment options into a connected accounts receivable experience. The product story had moved well beyond a card terminal. Yet the recurring problem remained recognizably human: someone needs to know who has paid, who has not, and what to do next.
- 01 Send the invoice
- 02 Let the customer pay
- 03 Track what arrived
The neighborhood remains part of the job
Oddo’s interests extend beyond the payments business. He is president of Bobo Co. Development, which owns and operates apartments in the Kansas City area. He also serves on the board of the Police Athletic League of Kansas City, Kansas. Away from those roles, he enjoys tennis and coaching youth sports. He and his wife have three sons.
The community commitments have a place inside Basys as well. In 2022, the company described an annual $500 charitable contribution for each employee to direct to an organization of their choice. It planned to add a paid volunteer day in 2023. The employee gets a say in where help goes, instead of receiving a preselected cause with the company announcement.
Another partnership, described in 2020, involved sponsoring 11 children through the Kansas City nonprofit Unbound. The appeal for Oddo included the relationships that developed through the arrangement. Taken together, the programs suggest why his language about people recurs so often: his business, local commitments and preferred way of managing overlap in quite practical ways.
EY named him a Heartland Entrepreneur Of The Year finalist in both 2025 and 2026. Recognition provides a date and a title for a career whose more characteristic moments are smaller: a completed degree in rival colors, a familiar merchant’s voice, an employee returning with travel pictures. Those are the details that make his account of leadership feel inhabited.
The software will keep changing. The proposition Oddo asks colleagues and customers to judge is more durable, and more demanding: whether working with his company is an experience they would choose again. Every fifth year, at least one answer arrives with a suitcase.