Stripe Sessions 2025 Review

In May 2025, I travelled to Stripe's product conference, Sessions, in San Francisco. We in Square1 are long-term Stripe partners, and have regularly attended the European-based events, but this was my first time making the trip Stateside.

The Future - Coming Soon

At Sessions, Stripe have a relentless slate of product announcements - mixing new products with upgrades to existing functionality. Some of the highlights for me were:

Workflows and Scripts

Workflows are programmable flow state machines. Through a user-friendly GUI, rules can be built to fire automatically within Stripe, e.g. "If we get a payment from a new customer AND the amount is over $10,000, THEN set the member_status metadata to VIP THEN email my loyalty team with customer details".

This tool popped up in quite a few different demos - Stripe's multi-processor orchestration also made use of this, e.g. "If payment is >$X AND customer country is UK, route to Adyen, ELSE route to Stripe". This looks like being an incredibly powerful feature - I can already think of half a dozen projects where we've a collection of lambdas and one-off scripts to handle these kind of simple actions, which can all be replaced by this native workflow builder. It's another interesting step in the [LINK] no-code direction, enabling deeper facility within the Stripe platform for non-technical users.

Scripts are another very interesting area of customisation for core Stripe functionality. Again the idea is to move customisations that currently live in our apps back into the Stripe core. The example shown is around calculation of a discount amount. Depending on different customer attributes, maybe we offer a 10% discount, maybe 20%, maybe 0. Small scripts can be written to override this calculation behaviour, and pushed to Stripe from the CLI. The function then will run natively inside Stripe. This one is very interesting, and is a little further from prime-time launch readiness than workflows. It'll be very interesting to see what sort of visibility there is within the Stripe platform once they're deployed (how can I tell what scripts my team have deployed to run on my account?), whether there's versioning, and how the running of scripts shows in things like payment detail reports, but it's a release I'll be keeping a close eye on!

Stablecoins

Stablecoins, and cross-border transfers in general, seem set for "a moment". A refreshed dashboard showing simplified management of multiple currencies looks exciting. In an AMA Patrick Collison mentioned "the assumption that one customer will only every one currency" as one of the things he'd do differently if he could start Stripe again, and these updates look like going a long way to solving that pain point. With the acquisition of Bridge, Stripe are going all-in on stablecoins as the backbone of cross-border commerce. When combined with stablecoin credit cards offered via Ramp, and improved payout options, it looks like a lot of existing barriers to cross-border commerce are going to come tumbling down.

AI

AI of course got plenty of mentions. We've moved past the point of AI being a discussion point in and of itself - it was woven into every talk, every product launch, and into John Collison's own vibe coded work on the conference app. The step-change in detection of card testing networks thanks to Stripe's own AI model was particularly impressive (59% detection rate to ~97%). Cursor founder Michael Truell also had a great talk on the challenges of building AI tools for developers, the benefit of dogfooding, and the need to quickly kill features that don't work.

Agentic Commerce

There was a lot of conversation around agentic commerce too - potentially a huge market, but lots of challenges too. The idea here is that you can give an AI agent a restricted credit card, tell it "I need the best vacuum cleaner and some dishwasher detergent", and it works away in the backend to buy them from the best suppliers. How "the best" is defined here is a big TBC, but there's also a big question around merchant support for this kind of headless commerce. Plenty of merchants make serious money from in-checkout upsells. Think about Amazon and the "other customers also purchased.."-type units. If retailers no longer control the checkout experience, their ability to influence overall cart size will be fairly limited.

There was an excellent panel on this, with Stripe's Jeff Weinstein leading a conversation between Tracy Young (Rye), David Singleton (former Stripe CTO), and Paul Klein (Browserbase). Paul made a really intereating point about the possible parallels with "dark kitchens" that sprang up in the wake of food delivery apps - will we see "dark commerce" stores that can price more competitively if they have no web presence beyond the APIs called by AI? During this discussion, Jeff had a fascinating anecdote about Stripe's internal testing of MCPs. They had a server which could be called by an AI agent to generate emojis. At one point they enabled payment. On the next request, they asked the AI to get a cat emoji. The AI checked with the MCP, found that there was now a price, and, as expected, returned to the user for confirmation. "The cat emoji will now cost 10c. Would you like me to purchase it?" However, the AI then added ".. or would you like me to go ahead and generate one for you myself?", which was an unexpected curveball. Lots of interesting learnings ahead, when dealing with this sort of non-deterministic agent!

Updated payouts

A particularly-interesting new release is around the ability to do payouts directly from a Stripe account to an arbitrary third party. Think of something like a freelancer you want to pay from your Stripe balance. It'll soon be possible to enter an email address, an amount of money to send, and an email with link will be sent to the recipient. Once they enter their bank account details, the funds get transferred. This is something that at the moment is a lot trickier to do - there are a lot of hoops to jump through with Connect setup, KYC verification and the like, so this is a product launch I'm very much looking forward to. It'll be US and UK first, so it'll be interesting to see how quickly it can run the EU regulatory gauntlet and get live in EMEA.

More where that came from

A comment I heard from many of the Stripe folks at the event was that they'd had a lot of difficulty in trimming the product keynote down to just the big hitters. This year has apparently seem the cumulation of a number of multi-year bets coming together at once, which has led to a lot of new products finally seeing the light of day around the same time. There's a deeper write-up from a dev perspective on the Stripe dev blog.

Keynotes

The keynote guests were an interesting selection of contrasts - Mark Zuckerberg and Jony Ive are two captivating figures, with pretty much diametrically opposed energy levels. Zuckerberg had a lot to say about Facebook's investment in new technologies, and the challenges of being distributed on platforms controlled by your rivals ("Sundar is cool. Tim... He's had a bad week, I don't want to pile on" when asked about the two CEOs who control his distribution - think he has a favourite there..) His discussion with John Collison was pretty wide-ranging, though came back again and again to investment decisions. Facebook has made some big bets on "the next big thing", from VR/metaverse, to AR, and AI via Llama, so hearing Zuckerberg talk through his reasoning for continued high investment was interesting.

Jony Ive brought a radically different energy in his discussion with Patrick Collison. Dressed all in white, with the calm energy of a Zen Buddhist, he spoke at length about the importance of finding meaning in what we build, and remembering the human at the heart of what we do. He felt it key to obsess over small things, like the paper cord wrapper on the iPhone cable, so whenever it is opened up, the end user has a subtle "someone gave a shit about this" moment. He mentioned the importance of designing for others, and his design team at Apple regularly having meetings in each other's homes, rather than stuffy conference rooms. The theory is that everyone is on their best behaviour, but also comes to appreciate the human behind the decisions and discussions. It was a fascinating conversation, with some interesting detours into Victorian architecture. For all of human history, streets had been littered with running sewage. In Victorian London, they put a sewer in place, so effectively from one day to the next, the streets went from filthy to clean, and opened up a host of other benefits for citizens of London. The machines that enabled this were the pumping stations, which were housed in grandiose buildings, befitting of their status and achievement.

Dwarkesh Patel has written what John Collison called a definitive history on how AI has gotten to where it is today, and had a lot to say on the impact of AI on GDP ("imagine we've added a few billion extra workers - what impact should that have?"). The mayor of San Francisco, Daniel Lurie, talked about housing challenges, and the "a lot done, more to do" approach to improving crime levels and life overall in San Francisco since his tenure began.

Partnering up

One thing Stripe does very well is the Partner ecosystem. As long-standing Stripe partners here at Square1, there was a full slate of events to network with other partners, sharing various battle stories from around the globe! Terry Wise's session walked through the growth of the partner ecosystem, and how Stripe is working to make it easier for partners to build on top of Stripe. As part of this, it was an honour to be named a Stripe Advocate, among a very impressive group of partners.

Expo

The expo attached to the event was pretty cool. There was a mix of Stripe-hosted and exhibitor booths, covering pretty much every aspect of the ecosystem. There was a stablecoin demo to pay for coffee, and across the floor "revenue recapture" seemed to definitely be a hot topic for a lot of exhibitors. There was also a booth to get free professional headshots, which was a fun touch.

Downtime

It was my first time in San Francisco, so I had to fit in some sightseeing! My father worked for years in a job which allowed him to travel the globe to various meetings, but unfortunately to see very little of it directly. "How was Istanbul?" "Well, the hotel at the airport was fine. The train to the conference venue was ok. And the airport was ok. Beyond that... 🤷". So when I'm trevalling to events, I try to fit in a little bit of downtime, and to see the area I'm in. I managed to squeeze in a trip to Alcatraz, which was fascinating. The audio tour was really well done, and it was interesting to see how the prison has changed over the years. I took a run out to the Golden Gate Bridge, which was great to see up-close. Less great was the number of hills around the city - much hillier than even it looks in the movies!

San Francisco as a city is very interesting. There's a lovely area down by the harbour, very tourist-friendly. And there's a real tangible energy to the place. It's fascinating to come from home, where all the on-street billboards are for food, beer, TV shows 9Lot of FMCG, essentially), to an area where the billboards are almost universally for some SAAS or other. Some I'd heard of, some I'd never come across in my life. But a definite palpable energy to the place, which even my hardened euro-pessimist self found infectious pretty quickly.

The flip side of that is that there are still areas where you can understand San Francisco's recent bad reputation. Walking down one long street, you pass fancy shops and retail outlets, with well-to-do people going about their business, then 50 yards down the same street, cross a set of lights, and there are people out of their minds in a zombie-like state trudging back and forth across the pavement. Every city has areas to avoid after dark, what surprised me in SF was that these were less discrete areas, and more short portions of specific streets, easy to stumble into if you weren't watching where you were going. From speaking to some of the locals, this has apparently improved a lot in the last year, but it's still quite jarring to go into a convenience store and find that literally everything is behind "please call attendant" glass.

Overall, it was a great event. The energy was high, and the Stripe team were on top form. It was great to see so many familiar faces, and to meet some new ones too. The food was excellent, and the venue was perfect for the event. I can't wait to see what Stripe has in store for us next year!