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§ Private Profile · 1850 Gateway Dr UNIT 125, San Mateo, CA 94404, USA
Digital payment platform for businesses to send and receive real-time push payments, including digital checks, ACH, and virtual cards.
Based in San Mateo, California, Checkbook operates a digital payment platform that enables businesses to send and receive real-time push payments, including digital checks, ACH transfers, and virtual cards. The SaaS platform facilitates instant fund transmission without requiring recipients to register or download an application, effectively replacing traditional paper checks with lower-cost online alternatives. Operating with fewer than 25 employees, the fintech company generates under $5 million in annual revenue by serving businesses that manage complex accounts payable and receivable workflows. Checkbook has raised a total of $13.05 million in funding, which includes a $10 million Series A round backed by institutional investors such as MassMutual Ventures, IA Capital, JPMorgan Chase, and Cross River Digital Ventures. Currently led by Co-CEOs Pia Thompson and Aditya Raikar, the organization was originally founded in 2015 by PJ Gupta.
Checkbook has raised $12.0M across 2 funding rounds.
Checkbook has raised $12.0M in total across 2 funding rounds.
# High-Level Overview
Checkbook is a financial technology company building a push payments platform designed to modernize how businesses disburse funds at scale.[2] The company's mission is to solve the challenges of push payments by creating a payouts platform for the digital age, addressing the inefficiencies of traditional payment methods like paper checks.[2] Checkbook serves businesses across multiple verticals—from marketplaces and gig economy platforms to accounting software providers and financial service companies—enabling them to send payments quickly, securely, and without hidden fees.[4]
The core problem Checkbook addresses is significant: according to the Federal Reserve Payments Report of 2018, more than 15 billion paper checks were sent within the US annually.[2] Checkbook's platform replaces this outdated infrastructure with real-time digital payment options, including digital checks, ACH payments, instant card transfers, and virtual cards.[5] The company operates with a straightforward pricing model—no percentages, no hidden fees—making it accessible to small and medium-sized enterprises (SMEs) that need to reduce manual errors, save time, and improve cash flow management.[3]
# Origin Story
The search results do not provide specific information about Checkbook's founding year, founders, or early traction milestones. However, the company is based in San Mateo, California, and operates as a lean organization with fewer than 25 employees.[3] The company has raised $10.2 million in total funding across two rounds, with the most recent funding round at $10 million, indicating investor confidence in the digital payments space.[3]
# Core Differentiators
Checkbook's competitive advantages center on simplicity, flexibility, and developer-first design:
# Role in the Broader Tech Landscape
Checkbook operates at the intersection of two powerful trends: the digitization of financial infrastructure and the rise of distributed work and marketplace economies. The shift away from paper checks represents a decades-overdue modernization of business payments—a market where incumbents have moved slowly. As gig economy platforms, freelance marketplaces, and accounting software providers proliferate, the need for efficient, scalable payment disbursement has become critical infrastructure.
Checkbook's positioning as a horizontal platform—serving marketplaces, accounting software, and financial services companies—gives it leverage across multiple high-growth segments. By embedding payment capabilities into other platforms via API and white-label solutions, Checkbook influences how payments flow through the broader fintech ecosystem. The company's focus on SMEs and mid-market businesses also addresses an underserved segment that lacks the resources to build custom payment infrastructure.
# Quick Take & Future Outlook
Checkbook is well-positioned to capture share in the multi-billion-dollar B2B payments market as businesses accelerate their shift away from legacy payment methods. The company's lean team, strong funding position, and developer-centric approach suggest it can scale efficiently. Future growth will likely depend on deepening integrations with accounting and marketplace platforms, expanding internationally, and potentially adding adjacent services like invoice financing or payment analytics.
The broader trend working in Checkbook's favor is the consolidation of financial operations into software platforms—businesses increasingly expect payments to be embedded, not bolted on. As this expectation becomes standard, Checkbook's role as a foundational payment layer could expand significantly, making it a critical piece of infrastructure for the next generation of business software.
Checkbook has raised $12.0M in total across 2 funding rounds.
Checkbook's investors include MassMutual Ventures, GPO Fund, Jonathan Wasserstrum, Cross River Digital Ventures, IA Capital Group, J.P. Morgan, August Capital, Citi Ventures, Founders Fund, Hubrix Ventures, Hyde Park Venture Partners, Lobby Capital.
Checkbook has raised $12.0M across 2 funding rounds. Most recently, it raised $10.0M Series A in October 2021.
| Date | Round | Lead Investors | Other Investors | Status |
|---|---|---|---|---|
| Oct 1, 2021 | $10M Series A | MassMutual Ventures | GPO Fund, Jonathan Wasserstrum, Cross River Digital Ventures, IA Capital Group, J.P. Morgan | Announced |
| Nov 1, 2016 | $2M Seed | — | August Capital, Citi Ventures, Founders Fund, Hubrix Ventures, Hyde Park Venture Partners, Lobby Capital, RRE Ventures, Marco Demeireles, Jonathan Korngold | Announced |