Stripe Hires AWS' Mike Clayville as Chief Revenue Officer

We're excited to hire Mike in part because AWS has been one of the very best examples ever of simultaneously selling to the largest companies in the world while not giving up on a strong self-serve product. So many B2B companies end up with homepages for which the only CTAs are annoying variants of "read case study", "download whitepaper", and "request a call". All stock photography; no product imagery.

Stripe's growth thus far has been fueled by individual developers and founders signing up and growing with us to billions of revenue. As we scale, the "impatient developer" will remain the focus of our product development.

Over time, however, we've been increasingly finding that large organizations (like Zoom/Atlassian/Maersk) want to adopt Stripe -- Stripe now has a lot of functionality that they can't get elsewhere. So, we're very eager to continue to grow this side of our business with Mike.

Congrats, Patrick. The VMware + AWS experience is certainly a big plus for a company like Stripe.

I would dare to disagree on, or at least to challenge, the "simultaneously" that you mention, though - in my experience (ex AWS, ex VMware) these two are completely different sales motions, made possible simply by the product itself and how it's discovered and consumed... Despite (yes, despite) what enterprise sales wanted to do. In a way, it's as if AWS self-serve were one entity, and AWS enterprise sales were another one.

In many cases, sales teams were completely not aware of certain things happening, or certain accounts becoming huge overnight, or certain developer behaviors. Some salespeople were handsomely rewarded for having been randomly selected as the sales rep for accounts like, say, Dropbox or AirBnB.

It's hard to describe properly, I know, but it's not as harmonious as one might say at first glance. And I think that the sales team still hasn't a good idea of the other side of the coin.

In a way, AWS' merit is to not have let Enterprise Sales screw up the self-serve part, and I think that's mainly because AWS was, and still is, so much more metric-driven than any other business I'm aware of. Enterprise Sales happened gradually, without interrupting a very addictive self-serve machine.

Anyway, this could be a long conversation with lots of platitudes, so I'll stop here and try to think of better ways to explain what I have in mind.

The number of companies (big ones, public ones!) where I can't for the life of me figure out what they sell from their website is truly astonishing. I understand that 1) if I can't understand it I'm not in their market, and 2) they probably want to be vague so they can sell their prospects whatever they ask for [1] but I still feel that they could gain a lot in the long term through brand awareness and people like becoming or meeting their target customer (but not having had any idea what that company did) by making a clear articulation of what the hell they do.

[1] Funny story, I was at a market in India and asked a guy selling toys and things if he had any fireworks. He asked me a lot of questions about what I wanted, but I couldn't see any evidence of him having such a wide variety of stuff. Then he sprinted off and asked his neighbor vendor to watch his stall. He came back 5 minutes later with a ton of fireworks to my liking, I bought what I wanted and then he went back to the fireworks guy with his leftovers. I assume that in a split second he negotiated a deal with that guy where he borrowed the fireworks, sold me what he could, and took the rest back. I don't know what he marked me up but I hope it was a lot.

Often not, but it's considered rude to point out examples thereof.

I think that the infrastructure market naturally breeds a lot of products for pretty specific/narrow use cases, whereas our strategy is more about marrying financial capabilities with very broad/flexible APIs. Given that, we've always valued very cohesive and composable functionality between the different facets of Stripe, having a straightforward and tightly integrated Dashboard, and so on. (That's no criticism of AWS -- we haven't launched 100+ different products and we aren't going to have a product suite as extensive as theirs any time soon.)

I do think that software complexity lifecycle management (and how that pertains to organizational considerations) is one of the tough problems in our industry. AWS has done an amazing job in terms of their pace of development and innovation, but, yes, it's also become a pretty complicated suite. I think we all currently face some kind of "fast development", "cohesive integration", "broad functionality" trilemma and how best to surmount it seems a big open question to me.