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

10/26/25
Source: Lenny’s Newsletter by Lenny Rachitsky. Read the original article

TL;DR Summary of How Block CTO Dhanji Prasanna Transformed AI Productivity

Dhanji R. Prasanna, CTO of Block, spearheaded an AI-driven transformation that significantly boosted company productivity. The internal open-source agent Goose saves employees 8 to 10 hours weekly, impacting various teams beyond engineering. Leadership’s daily use of AI tools was critical for widespread adoption, while organizational changes also played a major role in enhancing output. Insights from past product failures informed Block’s AI and product strategies for success.

Optimixed’s Overview: Driving Business Impact Through AI Integration and Leadership at Block

Transforming a Tech Giant with AI-First Strategies

Dhanji R. Prasanna, as CTO of Block (formerly Square), has led a vast engineering team of over 4,000 people, turning the company into one of the most AI-native large enterprises globally. His vision began with an “AI manifesto” that convinced CEO Jack Dorsey to embrace an organization-wide AI transformation.

Key Innovations and Productivity Gains

  • Goose Agent: Block’s internal open-source AI assistant, Goose, has saved employees approximately 8 to 10 hours each week by automating routine tasks and streamlining workflows.
  • Cross-Functional AI Benefits: Contrary to common assumptions, AI productivity gains were realized most significantly in non-engineering teams, showing AI’s broad applicability across business functions.
  • Leadership Adoption: Daily usage of AI tools by company leaders was essential to foster adoption and trust throughout the organization, demonstrating a top-down commitment to innovation.

Beyond AI: Organizational Change and Product Insights

While AI tools delivered measurable productivity improvements, Prasanna highlighted that certain organizational changes had an even greater impact on team effectiveness. He also challenged the conventional wisdom that code quality directly correlates with product success, emphasizing the importance of user focus and market fit.

Learning from Failure to Fuel Success

Drawing on lessons from previous projects like Google Wave and Google+, Prasanna applies a pragmatic approach to product development and AI integration. This experience helps Block avoid common pitfalls and accelerate innovation.