In a significant strategic realignment, the US business payments platform Checkbook has announced an immediate transition to a co-CEO leadership model, appointing company insiders Pia Thompson and Aditya Raikar to the top executive positions. The move signals a new chapter for the fintech firm, which has spent the last nine years modernizing B2B payments away from traditional methods by championing digital solutions like ACH, real-time payments, and virtual cards. This carefully planned succession sees founder PJ Gupta stepping aside from the daily operational leadership he has held since the company’s inception in 2015. The appointment of two internal leaders, rather than an external hire, suggests a focus on continuity and an acceleration of existing strategies. This dual-leadership structure is poised to leverage the distinct yet complementary expertise of its new leaders, aiming to navigate the increasingly complex and competitive digital payments landscape with a multifaceted approach to growth, compliance, and innovation. The transition marks a pivotal moment for the company as it prepares for its next phase of expansion.
A Dual Approach to Leadership
The selection of Pia Thompson and Aditya Raikar as co-CEOs introduces a dynamic leadership paradigm built on their specialized and extensive backgrounds in the financial services sector. Thompson, who joined the company earlier this year, brings a crucial legal and compliance perspective shaped by her experience as general counsel for several fintech firms. Her continuation in the role of general counsel alongside her co-CEO duties ensures that regulatory diligence and corporate governance are embedded at the highest level of strategic decision-making. Complementing this is Aditya Raikar, who has been a key driver of the company’s expansion since his arrival in 2022. Having advanced from VP of growth and partnerships to chief revenue officer (CRO), a title he will also retain, Raikar offers deep expertise in market penetration and strategic alliances, honed during his tenure at Citi, including his time as a senior vice president for Citi Ventures D10X. This combined leadership, with over 35 years of collective experience, creates a powerful synergy that merges rigorous legal oversight with aggressive growth and revenue generation strategies under a unified vision.
The Founder’s Evolving Role
The leadership transition also redefines the role of Checkbook’s visionary founder, PJ Gupta, who has moved into the position of executive chairman. This shift is not a departure but a strategic evolution, allowing Gupta to step back from day-to-day operational demands while remaining deeply involved in the company’s long-term direction. His statement that he was “ready to build again” indicates a renewed focus on high-level innovation and strategic initiatives, leveraging his deep institutional knowledge to guide the new leadership. This move is widely interpreted as a sign of the company’s maturity, marking a successful transition from a founder-led startup to an institution with a robust and sustainable leadership structure. The appointment of Thompson and Raikar, coupled with Gupta’s continued strategic involvement, cements a foundation that balances operational excellence with a forward-thinking vision, positioning the company for its next stage of growth in the competitive fintech arena.
