For me, Stripe’s annual letter is a moment that I’m waiting for. There are so many leadership and business lessons in each letter. Here are the most important insights for me:
1/ Stripe is no longer just a payments company, it’s an economic engine.
With $1.4 trillion in total payment volume in 2024, Stripe now processes the equivalent of 1.3% of global GDP. That’s a staggering number for a company that started as an API for developers to accept credit cards. But more importantly, it highlights that Stripe is building the financial infrastructure of the internet economy and that economy is growing much faster than traditional industries. Unlike legacy financial institutions, Stripe operates as a programmable platform, which allows its customers to move, transact, and monetize faster than their competitors.
2/ Profitability matters now, but reinvestment still defines Stripe’s strategy.
Stripe was profitable in 2024 and expects to remain so in 2025. This is a big shift from the growth-at-all-costs mentality of the last decade, but it also reflects the new reality of tech: profitability is power. However, instead of hoarding cash or distributing dividends, Stripe is doubling down on reinvestment into R&D at an industry-leading rate. This is particularly relevant given the emerging trends in stablecoins, AI and financial automation, all areas where Stripe wants to dominate before others catch up.
3/ Billing is becoming a core part of Stripe’s future.
While Stripe started with payments, subscription billing is becoming its next major revenue driver. Stripe Billing is now a $500 million business, used by over 300,000 companies, and managing 200 million active subscriptions. The real significance? Billing isn’t just about collecting recurring payments, it’s about automating revenue operations for the AI era. Companies are increasingly embedding machine commerce, and Stripe is positioning itself as the default financial infrastructure for this transition.
4/ Legacy companies are modernizing with Stripe, and that’s a huge deal.
It’s easy to think of Stripe as a platform for startups, but half of the Fortune 100 are now customers. The company highlights organizations that have been around for centuries, like Oxford University, the Church of England, and PepsiCo, now running digital payments through Stripe. This shift reflects a broader truth: every company, regardless of age, must now operate like a software company. Stripe it’s giving legacy enterprises a way to reinvent themselves before they get disrupted.
5/ AI-native businesses are growing at an unprecedented pace.
Stripe’s letter is filled with AI-related stats, but one stands out: more than 700 AI agent startups launched on Stripe last year. Companies like OpenAI, Perplexity, and ElevenLabs aren’t just using Stripe to process payments, they’re building AI-native business models that depend on instant, automated transactions. The broader implication? AI is fundamentally changing how businesses interact with money, and Stripe is making sure it owns the financial layer of this transformation.
6/ Vertical SaaS is the hidden force behind small business growth.
Traditional SMEs are thriving again, not because they’re going digital, but because software is being built specifically for them. Stripe’s letter cites platforms like Slice (for pizzerias), Traxero (for tow truck operators), and Clio (for law firms), all examples of vertical SaaS businesses that act as financial platforms for their industries. This is a fundamental shift: Stripe it’s enabling software-driven economies at every level, including small businesses that previously couldn’t access this kind of technology.
7/ Stablecoins are Stripe’s next big bet, because money itself is changing.
Stripe’s acquisition of Bridge, the leading stablecoin orchestration platform, signals a massive shift in financial infrastructure. Stablecoins make money movement cheaper, faster, and programmable, and Stripe is betting that they will become a core part of business transactions worldwide. While stablecoins have been largely a crypto-native phenomenon, Stripe’s push into the space suggests that they’re about to become mainstream for corporate treasury, global payroll, and real-world commerce, all of which Stripe is already positioned to handle. LINK
