Braintree
The payments company that chose enterprises over developers - and proved there's more than one way to win in fintech.
The payments company that chose enterprises over developers - and proved there's more than one way to win in fintech.
Founded in 2007, Braintree zigged where Stripe would later zag. Instead of seducing developers with beautiful APIs, Braintree targeted enterprises with high-touch sales, compliance expertise, and white-glove service. The company optimized for CFO priorities - reliability, security, audit trails, SLAs - not developer experience. This was the anti-Stripe strategy before Stripe existed.
When PayPal acquired Braintree for $800 million in 2013, the deal solved PayPal's existential problem: escaping eBay's gravity. PayPal was trapped serving eBay's marketplace; Braintree processed payments for the next generation of platforms - Uber, Airbnb, GitHub. Braintree's enterprise-grade infrastructure gave PayPal credibility with companies that would never touch basic PayPal integration. The acquisition was calving in reverse: the parent absorbed the offspring's capabilities to evolve into new markets.
The lesson: in nascent markets, multiple strategies can succeed simultaneously if they target genuinely different selection pressures. Developer experience (Stripe) and enterprise reliability (Braintree) aren't competing strategies - they're different adaptations to different customer needs. The mistake is trying to serve both; the insight is choosing one and dominating it.
Braintree Appears in 2 Chapters
Acquired by PayPal in 2013 for $800M, enabling PayPal's expansion beyond eBay's marketplace to serve broader merchant base including Uber, Airbnb, and GitHub.
Read about calving strategies →Took enterprise-first approach to payment processing, contrasting with Stripe's developer experience focus, proving multiple growth strategies can succeed in nascent markets.
Read about early growth strategies →