Meet the Team

Over 25 Years of payment processing leadership and industry innovation.

Leadership Team
Scott Okrasinski
Chief Revenue Officer

About

Scott brings more than 30 years of leadership, business development, and revenue growth experience to his role as Chief Revenue Officer at PenChecks. Since joining the company in 2015, he has helped shape PenChecks’ growth strategy, strengthen industry partnerships, expand market presence, and drive the development of innovative retirement distribution solutions that deliver meaningful value to clients and their customers.

As Chief Revenue Officer, Scott leads the company’s revenue strategy across sales, business development, strategic partnerships, and customer-focused growth initiatives. His collaborative leadership style and deep understanding of the retirement services industry have helped position PenChecks as a trusted provider of retirement distribution, automatic rollover, advisor IRA strategy, and custody solutions.

Before joining PenChecks, Scott served in several executive leadership roles across diverse industries, including positions as President of The IndusTRI Group, Vice President of Sales for Creative Communications / Motorola, and Vice President and Partner of Queen City Reprographics / Resource Imaging Supply. These experiences provided him with a broad business foundation in organizational leadership, revenue optimization, operational management, and customer engagement.

Scott earned a Bachelor of Science degree in Criminal Justice from the University of South Carolina and remains committed to continuous learning, leadership development, and mentoring future business leaders.

Executive Profile

While attending the University of South Carolina, Scott initially envisioned a career in law enforcement or the FBI. However, an early opportunity in technology sales revealed a passion for helping organizations solve problems, build relationships, and achieve meaningful business outcomes. That discovery launched a career spanning more than three decades of sales leadership, executive management, and strategic growth.

Throughout his career, Scott has believed that lasting success begins with trust. His leadership philosophy centers on building strong relationships, understanding customer challenges, and developing solutions that create long-term value. Since joining PenChecks in 2015, he has championed a customer-first approach that aligns sales, product, operations, and service teams around a common goal: helping organizations simplify retirement distribution processes while delivering exceptional customer experiences.

As a member of the executive leadership team, Scott plays an active role in shaping the company’s strategic direction. He works closely with industry partners, clients, and internal teams to identify emerging market opportunities, guide product innovation, and ensure PenChecks continues to evolve alongside the needs of the retirement industry.

“People don’t buy products, they buy confidence and trust,” says Scott. “Our responsibility is to understand our clients’ challenges, help them navigate complexity, and deliver solutions that make their jobs easier while creating better outcomes for participants.”

One of the most rewarding aspects of Scott’s role is engaging directly with clients and industry partners. These conversations provide valuable insight into evolving market needs and help guide the company’s ongoing investments in products, services, and technology. His ability to connect customer feedback with strategic business initiatives has been instrumental in helping PenChecks remain responsive and innovative.

Scott is especially proud of PenChecks’ mission of reuniting people with their retirement savings and helping participants achieve better financial outcomes. He believes the company’s success is measured not only by growth and innovation, but by the positive impact it makes on the individuals and families it serves.

Hands-On Coaching

Scott considers getting out in the field and interacting with PenChecks clients and the sales team as the best part of his job. Consequently, he spends a lot of time on the road, crisscrossing the country to conduct joint sales calls with PenChecks’ Regional Territory Directors. Afterwards, he conducts feedback sessions to review what they did well and coach them on how to get better at identifying and understanding client needs and presenting the best solution for their situation.

Keeping in close contact with PenChecks clients enables Scott to have an important voice on the management team and make a real impact on the company’s ongoing efforts to improve client service. He also strongly supports the PenChecks mission of reuniting people with their retirement money and doing the right things for clients.

“What I really like about working at PenChecks is we pay people,” he says. “Other financial institutions talk about how much money they manage. We measure success in terms of how much we pay out each year. I also like the fact that our company president is a serial entrepreneur. He continually pushes the envelope to develop new products and services that address problems he hears within the industry, and he’s been doing it since PenChecks first opened its doors. It’s exciting working for a company that is constantly evolving and creating new solutions.”

When not on the road, Scott spends as much time as possible with his two children, ages six and five. An endurance sport enthusiast, he enjoys swimming, biking and running, and has completed two Ironman triathlons and numerous marathons. As a testament to the value of hard work and training, Scott improved his Ironman time by four hours in his second try!

Quick Links:

Life is too short to just have a job.

Calling All Career Seekers.

We’re looking for team players. Browse our current opportunities: