Checkbook, a leading innovator in digital payment solutions, has announced the appointment of Pia Thompson and Aditya Raikar as Co-Chief Executive Officers, effective immediately. The leadership transition marks a new chapter for the company as founder PJ Gupta steps aside from the CEO role to focus on guiding long-term strategy as Executive Chairman of Checkbook’s Board.
Gupta, who founded Checkbook in 2015, has been instrumental in building the company from an early-stage startup into a recognized leader in modern digital payments. As Executive Chairman, he will remain actively involved in shaping the company’s vision while also exploring new opportunities to innovate within the financial services ecosystem.
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Together, Thompson and Raikar bring more than 30 years of combined experience across fintech operations, product development, partnerships, revenue growth, and regulatory compliance. Their complementary backgrounds position them well to lead Checkbook through its next phase of growth as demand for scalable, compliant digital payment infrastructure continues to rise.
Scott Thompson, a Checkbook board member and CEO of Tuition.io, credited Gupta’s leadership with defining the company’s success to date. He noted that as Checkbook enters a new stage of expansion, the transition to new leadership creates an opportunity to build on a strong foundation. He added that Thompson and Raikar bring deep industry expertise, proven leadership, and a forward-looking vision to guide the company into its next chapter.
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Reflecting on the transition, PJ Gupta described the past decade as a meaningful and rewarding journey. He emphasized that Checkbook has remained committed to simplifying and modernizing payments for businesses of all sizes and expressed confidence that Thompson and Raikar are the right leaders to continue supporting employees, customers, and partners as the company evolves.
In a joint statement, Thompson and Raikar said they were proud to step into the Co-CEO roles and build on the culture of innovation that has defined Checkbook since its early days. They highlighted their focus on strengthening customer and partner relationships while continuing to demonstrate the value Checkbook delivers across industries as digital payments continue to transform how businesses operate.
Alongside their new responsibilities, Thompson will continue serving as General Counsel, and Raikar will remain Chief Revenue Officer, ensuring continuity across legal, compliance, and growth initiatives.
Before joining Checkbook, Thompson held senior legal leadership roles across fintech and consumer finance companies, where she oversaw capital markets activity, 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 earned her Juris Doctor from the University of Michigan Law School and holds a Bachelor of Arts from Wellesley College. She is licensed to practice law in Illinois.
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Raikar brings extensive experience from Citi, where he held senior leadership roles focused on growth and innovation. He previously led expansion efforts for Bridge, built by Citi, and worked within Citi Ventures D10X, helping launch multiple ventures across Citi’s institutional businesses. Earlier in his career, he worked in markets trading special situations and emerging market foreign exchange. Raikar is a graduate of Northwestern University.
With new leadership in place and its founder continuing to provide strategic guidance, Checkbook is positioning itself to accelerate growth while remaining focused on innovation, trust, and the future of digital payments.
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