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  1. Lenny's Podcast: Product | Career | Growth
  2. How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna
How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna

How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna

Lenny's Podcast: Product | Career | Growth · Oct 26, 2025

Block CTO reveals how their open-source AI agent, Goose, saves engineers 8-10 hrs/week & why org structure trumps AI for productivity.

Block’s Shift to a Functional Org Structure Was More Impactful Than Any AI Tool

Block's CTO reveals a counterintuitive lesson: reorganizing from a GM-based structure to a functional one (where all engineers report to one org) was the key to their AI transformation. This structural change had a greater productivity impact than any specific AI tool they implemented.

How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna thumbnail

How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna

Lenny's Podcast: Product | Career | Growth·4 months ago

Block's AI-Forward Teams Save 8-10 Hours Per Week, Setting a New Productivity Baseline

Block's CTO quantifies the impact of their internal AI agent, Goose. AI-forward engineering teams save 8-10 hours weekly, a figure he considers the absolute baseline. He notes, "this is the worst it will ever be," suggesting exponential gains are coming.

How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna thumbnail

How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna

Lenny's Podcast: Product | Career | Growth·4 months ago

YouTube's Success Proves Code Quality and Product Success Are Uncorrelated

Block's CTO argues that engineers mistakenly equate code quality with product success. He uses the example of early YouTube, which had a famously poor architecture but became wildly successful, while the technically superior Google Video failed. The focus should be on solving a user problem, not on perfect code.

How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna thumbnail

How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna

Lenny's Podcast: Product | Career | Growth·4 months ago

Non-Technical Teams See AI's Biggest Productivity Gains by Building Their Own Tools

At Block, the most surprising impact of AI hasn't been on engineers, but on non-technical staff. Teams like enterprise risk management now use AI agents to build their own software tools, compressing weeks of work into hours and bypassing the need to wait for internal engineering teams.

How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna thumbnail

How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna

Lenny's Podcast: Product | Career | Growth·4 months ago

Block's CEO and CTO Drive AI Adoption by Using Their 'Goose' Agent Daily

The key to driving AI adoption at Block was leadership by example. CEO Jack Dorsey and CTO Danji Prasana use their internal AI tool, Goose, daily. They argue this hands-on approach provides more insight into organizational workflow changes than any top-down mandate or analysis of industry reports.

How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna thumbnail

How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna

Lenny's Podcast: Product | Career | Growth·4 months ago

Idle LLMs Should Work 24/7 Building Anticipatory Features and Running Experiments

Block's CTO argues that LLMs are a wasted resource when they sit idle overnight and on weekends. He envisions a future where AI agents work continuously, proactively building features, running multiple experiments in parallel, and anticipating the needs of the human team so that new options are ready for review in the morning.

How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna thumbnail

How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna

Lenny's Podcast: Product | Career | Growth·4 months ago

AI Will Soon Enable Full Product Rewrites for Every Major Release

Contrary to the classic engineering rule to "never rewrite," Block's CTO believes AI will make this the new standard. He is pushing his teams to imagine a world where for every release, they delete the entire app (`rm -rf`) and rebuild it from scratch, with AI respecting all incremental improvements from the previous version.

How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna thumbnail

How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna

Lenny's Podcast: Product | Career | Growth·4 months ago

The Most and Least Senior Engineers Are the Eagerest Adopters of AI Tools

Block's CTO observes a U-shaped curve in AI adoption among engineers. The most junior engineers embrace it naturally, like digital natives. The most senior engineers are also highly eager, as they recognize the potential to automate tedious tasks they've performed countless times, freeing them up for high-level architectural work.

How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna thumbnail

How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna

Lenny's Podcast: Product | Career | Growth·4 months ago