Lenny Distilled

How Block is becoming the most AI-native enterprise in the world

October 26, 2025

Featuring: Dhanji R. Prasanna (Chief Technology Officer, Block)

9 quotes · 6 insights

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Strategy and structure must dance together

Conway's Law can be really, really powerful. So it's the law that basically says you ship your org structure. So what you're organized as in terms of teams, in terms of collaborating groups and your operating model matters a lot to what you build.
Dhanji R. PrasannaChief Technology Officer, Block 00:12:13
All engineers report into one single team now, all designers report into one single team and there's single head of engineering, single head of design, et cetera. And so that was the big transformation that we made, and that meant we could really drive forward AI, we could drive forward platform and just technical depth generally.
Dhanji R. PrasannaChief Technology Officer, Block 00:10:32
We're being more thoughtful about it. In the GM structure, our incentives were always to think of engineering headcount as a commodity. And so we would just add more engineers if we wanted to build more features and the classic mythical man person month trap. Moving to a functional structure completely changes that.
Dhanji R. PrasannaChief Technology Officer, Block 44:34

AI dramatically shifts productivity baselines

We find engineering teams that are very, very AI forward are reporting about eight to 10 hours saved per week. Whenever I hear a stat like this, I think an important element is this is the worst it will ever be. This is now the baseline. The truth is the value is changing every day, so you need to ride that wave along with it.
Dhanji R. PrasannaChief Technology Officer, Block 00:00:07
The non-technical people using AI agents and programming tools to build things is really what's been surprising and really amazing. The people that are able to embrace it to optimize for their particular work day and their particular set of tasks are really who are showing the most impact from these tools.
Dhanji R. PrasannaChief Technology Officer, Block 00:00:47

Cut scope, not quality

Start small with everything. If you try to boil the ocean to make a cup of tea, you'll never get there. So if you're making a cup of tea, just make the cup of tea. You don't need to boil all the water that there is.
Dhanji R. PrasannaChief Technology Officer, Block 01:08:26

AI is reshaping everything - adapt urgently or become obsolete

"This notion" refers to the idea that AI isn't a cure-all solution, mentioned in the context of discussing AI productivity gains.

Companies that started just with AI startups mostly, but there is some truth to this notion that AI isn't a panacea and it's growing as well in capability. So you need to ride that wave along with it. A lot of companies aren't realizing this. They're like, 'Well, where's the value?' And the truth is the value is changing every day.
Dhanji R. PrasannaChief Technology Officer, Block 00:17:17

The job evolves but the why remains constant

I think there's a trap in getting away from your core purpose as a company. Our core purpose is economic empowerment. Anything that serves that purpose, we should encourage and we should invest in, but if we're just purely looking at dollars versus dollars, then that's pulling us off that purpose.
Dhanji R. PrasannaChief Technology Officer, Block 00:40:31

AI adoption starts with leadership doing the work

Goose is Block's AI programming tool and agent that can automate tasks and control computers using Apple Script and other extensions.

Really try and use these tools yourself. The way in which I think we've been able to drive most of the adoption is Jack uses Goose, I use Goose, our executive team all have used Goose and use it regularly and use other AI programming tools and assistance as well, and we do it every single day.
Dhanji R. PrasannaChief Technology Officer, Block 54:04

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