Over the past few months, founders and pricing leaders joined us at Stripe Sessions in San Francisco and Stripe Tour stops in London, Paris, and Berlin to discuss how AI is transforming the economics of software. Across these conversations, a common theme kept surfacing: the revenue playbook that built the last generation of successful companies is breaking down. 

Leaders are already adapting by speeding up pricing iteration and preparing for the rise of the nonhuman buyer. Here are five shifts we’re seeing. 

Always-on pricing iteration requires new ways of working

In her first year at Lovable, Head of Growth Elena Verna made 10 pricing changes. That pace would have been unusual just a few years ago. But for AI-native companies, pricing has quickly become something they need to revisit more than once a year, or even once a quarter. Products change too quickly for pricing to stay fixed for long, and companies are still learning what resonates with customers. 

Across our conversations in San Francisco, Paris, London, and Berlin, leaders made it clear that internal processes must change in order to achieve the necessary pace of pricing iteration. They found traditional pricing committees too slow and unwieldy to keep up. At Stripe Tour London, Aisling O’Reilly, Fin’s head of pricing, described the “chaos” of the team’s previous large pricing committee meetings. With 20 people weighing in, there were too many stakeholders and too few decisions made. She and other AI leaders described how they moved to more streamlined processes—or even a single pricing owner.

Having a designated person prevents a dilution of responsibility; it ensures that whether there’s good news or bad news, everyone knows who to talk to.

The stakes of getting pricing right are high: leaders agreed that the risk of standing still is often greater than the risk of being wrong. If a competitor moves more quickly and launches a pricing model that resonates, slower firms miss their opportunity to connect with customers.

As an AI-native company, I would say the window of opportunity collapsed from years to weeks or sometimes months. So you need to be really fast.

The focus on ARR is holding software companies back from more flexible monetization

For companies with seat-based or subscription revenue, introducing usage-based pricing can feel risky: there’s concern around “cannibalizing” predictable ARR by moving existing subscription customers to metered billing. 

But the greater threat is losing customers altogether. If customers want more flexible, usage-based access, they might not stay with a rigid subscription model—especially if an AI-native competitor is offering the pricing structure they expect. 

We’re seeing some early indications that usage-based pricing might not undermine ARR as much as many teams expect. Verna described Lovable’s decision to introduce credit top-ups alongside a subscription model—a move that might have been perceived as disruptive to predictable revenue. Instead, the company found that top-ups started to behave a lot like recurring revenue:

The fascinating part about this is that it did not reduce our ARR… Top-ups started acting like recurring revenue. Repurchase rate of top-ups was just as high, if not higher, than subscription renewal rates.

Active, recurring usage also offers a strong indication of alignment between the price charged and the value derived by customers. And unlike with a subscription, there’s no ceiling on revenue per customer for a company’s most active users.

The agent customer is arriving, and pricing and payments need to be redesigned for it

Both AI-native companies and traditional enterprises are wrestling with the same question: what happens when the buyer isn’t a person? For AI-native companies, the shift means designing for agent-led discovery, evaluation, and purchase from the start. Vercel CEO Guillermo Rauch described how he’s now “sweating the details” of error messages, with the agent as the customer.

For more established businesses, the challenge is similar, but often harder to act on, since new agent-facing experiences need to work with existing infrastructure.

What if everything that is being done is getting orchestrated through these sort of AI agents, then what?… Can we actually execute a registration, log in to FOX One, payment, and then surface that content all under the hood back to the interface?

The businesses best positioned for what comes next will be those investing now in payments and pricing infrastructure that can handle agentic transactions as seamlessly as it handles human ones.

The move from product-led to sales-led growth motions is compressing from years to months

The top 100 AI companies by revenue on Stripe grew 120% on average in 2025. The same cohort is on pace to grow 175% in 2026. At that speed, companies are moving upmarket and building enterprise sales motions much earlier than previous generations of software companies, sometimes in their first year of operation. 

Part of the reason is direct demand from large enterprises, which require the kind of commercial engagement—like negotiating for volume discounts—that only a sales-led motion can support. At the same time, developers who discovered AI tools through self-serve, product-led channels are bringing them into their organizations as internal champions. This creates enterprise opportunities that AI companies don’t have to initiate themselves:

I have champions within enterprises that tell me, ‘Well, I was using Claude Code over the holiday break. I now want to bring the power of Claude plus Vercel to my enterprise.’ And so I think this world is continuing to converge.

Revenue infrastructure should support multiple ways of selling from the beginning, so the business doesn’t need a complete rebuild when enterprise demand arrives earlier than expected.

Rigid revenue infrastructure is becoming a ceiling on growth and experimentation

Underlying all four of the trends above is a shared operational constraint: revenue infrastructure built for a world of static, predictable pricing isn’t equipped to support AI-era monetization. But leaders also recognize that the future is too uncertain, and circumstances are changing too quickly, to optimize for any single model. Instead, Anthropic Engineering Manager Shaa Alagumuthu argued that platforms need to be flexible enough to absorb constant change, even when teams can’t predict what’s coming next.  

Leaders are also realizing that they can no longer compensate for clunky infrastructure by throwing people at the problem. At ElevenLabs, three product lines—ElevenCreative, ElevenAgents, and ElevenAPI—each have fundamentally different pricing structures, all iterating independently as customer expectations shift. Even the most dedicated team can’t brute force this pace of change:

You need to have the right instruments in place, both from a data infrastructure perspective, commercial infrastructure perspective… You have to [lean on technology], otherwise there’s really not enough people to manage it.

The right revenue infrastructure can become an engine of growth, but only if it’s flexible enough to amplify rather than limit a team’s monetization experiments. 

How Stripe can help product and finance leaders build for what’s next

At Sessions and Stripe Tour, we introduced major upgrades to our Revenue suite for both AI-native and enterprise businesses. 

For subscription businesses, Stripe Billing now supports a broader range of hybrid pricing models. At Sessions, we previewed the ability to create custom logic around invoice item routing, proration calculations, and customer balance settlement. We also previewed a new sales-led contract object, payment plans for automated installment collection, and subscription invoice revisioning. 

With Metronome, Stripe’s usage-based billing product, companies can now manage commits, multidimensional pricing structures, and bespoke contracts with real-time revenue visibility down to the account, contract, and product levels. They can access and update Metronome contracts, customers, and data directly in the Stripe Dashboard through the new Metronome app. And teams using complex, credit-based models can now track credit balances at industry-leading rates, receive instant low-balance alerts, and configure automatic top-ups.

We’re looking forward to continuing the pricing and revenue conversation. Join us at Monetize, an exclusive gathering for leaders shaping the future of pricing, billing, and monetization.