Every now and then, we come across a compelling fintech story that deserves more attention. Today, we are excited to introduce Checkbook, a company that was new to us as well, until we sat down with Co-CEO Aditya Raikar. Checkbook is a fintech company that provides an all-in-one push payments platform designed to simplify and modernize how businesses send outbound payments (disbursements).
Let us explain.
Aditya started at Citigroup on the trading floor, then pivoted to Citi Ventures (venture building/incubation side). He worked with Checkbook on a multi-party insurance initiative, helped them onboard, and later joined the company ~3.5 years ago at the founder’s invitation after leaving a spin-out project. He has held various roles and now serves as Co-CEO. Aditya was clearly energized by Checkbook’s growth prospects, and his responsibilities focus on customer-facing revenue, partnerships, and products; while his counterpart, Co-CEO, manages governance, finance, and risk.
What are Checkbook’s main functions?
The company enables an all-in-one push payments platform for B2C and B2B disbursements. It supports multiple rails: push-to-debit card (most popular, via Visa Direct partnership; ~30%+ of volume, favored for instant 24/7 use), ACH (second), RTP/FedNow, printed and mailed checks (yes, still used, though a smaller percentage of transactions but higher dollar value; includes a digital PDF “printed check” option for instant delivery), virtual cards, Venmo/PayPal, wires (least popular due to cost). There is more. They also offer a hosted, white-labeled payment portal or “box” solution for institutions choosing to manage B2C and B2B payments in house; a handful of large customers are live.
Which categories of businesses utilize Checkbook?
Checkbook primarily serves businesses in the United States, with some cross-border payment capabilities. The company targets organizations in three main customer buckets: (1) fintechs and embedded finance companies where payments are a core part of the product, such as earned wage access providers, ride-sharing platforms for driver payouts, rewards programs and insurance claims; (2) vertical software and ERP providers in industries like property management, construction, and hospitality that embed bill pay or disbursement features for their clients; and (3) established institutions, including insurance carriers, government programs, and class action administrators, that are actively digitizing their legacy paper check processes. Rather than focusing on company size, Checkbook emphasizes the importance of the use case, serving everyone from small teams overseeing high transaction volumes to large enterprises modernizing their disbursement systems.
How does the company differentiate itself?
Checkbook has built most of its platform in-house, maintaining direct connections to payment networks and banks wherever possible, with minimal reliance on third parties, including handling check printing and mailing internally. The company offers a simple and predictable pricing model: flat per-transaction fees, kept as close to cost as possible (under $1 for many payment rails), in contrast to the percentage-based fees common in the industry. Customers also pay a monthly platform subscription that varies based on the complexity of their use case, such as a combination of paper check, push debit, and virtual cards. Importantly, Checkbook imposes no minimum volume requirements or long-term commitments. On an operational level, Checkbook offers fast time-to-market, with customers typically moving from contract signing to full production in just days to a few weeks. What is more, Checkbook emphasizes reliable service, advisor style sales, and scalable infrastructure while prioritizing customer experience over aggressive growth.
How many customers and transactions does the company enable?
Checkbook processes millions of transactions per month across hundreds of customers, resulting in an annual dollar volume in the low tens of billions. The company is well positioned as a flexible, multi-rail solution for high-volume disbursement needs, including earned wage access, gig economy payouts, insurance claims, rewards programs, bill pay, and similar use cases. It stands out for its customer-centric approach: deeply understanding real money-movement needs, using an advisor-style sales process that avoids pushing unnecessary features, and delivering strong service with quick response times and problem-solving—even outside regular business hours. Growth has been driven primarily by customer referrals, supplemented by targeted outreach, industry conferences, and ongoing marketing experiments.
What do we think?
Checkbook simplifies a complex and often burdensome part of business operations by taking full responsibility for disbursements, allowing its customers to focus on growing their core business. In today’s environment, especially with the rise of AI, launching a new company or adding new features to an existing one has never been easier, as barriers to software development continue to fall. However, the regulatory, compliance, and technological demands of handling B2B payments are moving in the opposite direction, becoming significantly more complex and difficult. This growing divergence creates strong demand for specialized platforms like Checkbook and is a key driver of the company’s growth. Promising ideas that solve real, persistent problems tend to stand the test of time and Checkbook appears to be one of them.