Checkbook Names Pia Thompson and Aditya Raikar as Co-CEOs

Founder PJ Gupta to transition to role as Executive Chairman

Checkbook, a leading innovator in digital payment solutions, announced the appointment of Pia Thompson and Aditya Raikar as Co-Chief Executive Officers (CEOs), effective today. Thompson and Raikar succeed founder PJ Gupta, who has decided to transition the role of CEO to new leadership to set the foundation for the Company’s next stage of growth. Gupta will continue to serve as Executive Chairman of Checkbook’s Board while pursuing new opportunities to innovate financial services. Collectively, Thompson and Raikar bring more than three decades of complementary experience in optimizing operations, product and partnership development, and regulatory compliance for financial technology companies looking to scale.

“PJ has played a pivotal role in building Checkbook from an early-stage startup into a category-defining leader in digital payments. As the company enters its next phase of growth, it is the right moment for a new generation of leadership to drive Checkbook forward,” said Scott Thompson, Checkbook Board Member and CEO of Tuition.io. “Pia and Aditya bring deep industry expertise, proven leadership, and a bold vision that will propel the company into its next chapter.”

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“It has been a long and rewarding journey and an honor to partner with the most incredible team at Checkbook since we first launched in 2015,” said PJ Gupta, Checkbook Founder and Executive Chairman. “Over the past decade, we have stayed true to our mission of simplifying and modernizing payments for businesses of all sizes with products and solutions that help our customers thrive. I am confident that Pia and Aditya are the right leaders to guide Checkbook’s evolution as a Company and support our incredible colleagues, customers and partners.”

“We are proud to step into the role of Co-CEOs,” said Thompson and Raikar. “Checkbook has always been a dedicated group of trailblazers passionate about innovation in payments, no matter the industry or sector. We look forward to building on our work, strengthening our relationships with our valued customers and partners, and continuing to showcase the value Checkbook brings to the future of digital payments.”

In addition to their roles as Co-CEOs, Thompson and Raikar will continue to serve as General Counsel and Chief Revenue Officer, respectively.

Prior to joining Checkbook, Thompson served as General Counsel and Secretary for multiple fintech and consumer finance companies, where she led capital market transactions, regulatory strategy, enterprise compliance and board governance. She currently serves on the Advisory Board of CompliSun and the Governing Board of the Conference on Consumer Finance Law. Thompson holds a Juris Doctor from the University of Michigan Law School and a Bachelor of Arts from Wellesley College. She is licensed to practice law in Illinois.

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Before Checkbook, Raikar was a senior leader at Citi, leading growth efforts for Bridge built by Citi. Prior to that, he was at Citi Ventures D10X, an internal venture building unit within Citi. There, he helped take multiple ventures from ideation to launch across all of Citi’s institutional client businesses. He started his career in the markets business, trading special situations as well as emerging markets FX. Raikar graduated from Northwestern University.

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