Cross-Functional AI Adoption

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How Shutterstock Builds AI-Native Engineering Teams (starred)

Engineering Leadership Gregor·Aug 20, 2026

Deep-dive companion to the cross-company comparison: Shutterstock's ~350-engineer org, 2-pizza teams with 1 PM per 2 teams, one dedicated Tech Lead per team, and separate 6-week 'bet cycle' ML teams t…

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How Companies Build AI-Native Engineering Teams: OpenAI vs. Anthropic vs. Shutterstock vs. Others (starred)

Engineering Leadership Gregor·Jul 20, 2026

Side-by-side comparison of AI-native org structures: OpenAI's small 2-4 person teams with 1:30+ PM ratios and no ceremony, Anthropic's traditional 2-pizza teams where any engineer can be tech lead and…

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How Anthropic Builds AI-Native Engineering Teams: Inside Patterns from the Platform Engineering Lead

Engineering Leadership Gregor·Jul 1, 2026

Gregor interviews Katelyn Lesse, Head of Platform Engineering at Anthropic, on how Anthropic itself structures and operates AI-native engineering teams — the people who build the tools Neo's team uses…

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3 Myths of AI Transformation: Practitioner Learnings from Augment Code's VP of Engineering

Engineering Leadership Gregor·Jun 22, 2026

Gregor Ojstersek shares the full recording and insights from Vinay Perneti (VP of Engineering, Augment Code) speaking at Engineering Leadership LIVE in San Francisco. Topic: the 3 most common myths te…

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The Org Playbook for Engineering AI Transformation: Individual Gains Don't Automatically Scale

ByteByteGo·Jun 22, 2026

ByteByteGo's piece on how engineering orgs translate individual AI productivity gains into organizational-scale transformation. The framing — 'individual gains do not become organizational gains on th…

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Fiona Fung (Claude Code/Cowork Manager): Building Culture When Roles Blur and Agents Are Everywhere

Lennys Newsletter·Jun 21, 2026

Lenny's podcast episode with Fiona Fung, Manager of the Claude Code and Cowork teams at Anthropic. Topic: how to build and lead the most AI-native engineering team in the world, and how to maintain te…

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Community Thread: How AI Is Changing Product Operating Models

Lenny's Newsletter / Community Wisdom·Jun 13, 2026

The featured thread in the June 13 Community Wisdom digest is 'How AI is changing product operating models' — a Slack discussion among product leaders about how AI is restructuring the PM-engineering-…

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Building an iPhone App with Zero Technical Skills via AI — Cross-Functional Signal

Lenny's Newsletter / How I AI·Jun 1, 2026

A non-technical person builds a working iPhone app using Codex with no coding background. Documents the entire process including failure modes and recovery. Partly a signal about how AI tools are brea…

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Pinterest: #how-i-ai Slack Channel → 1,200+ Members → Company-Wide AI Coding Pathfinders

Engineering Leadership Gregor·Jun 7, 2026

Jordan Cutler (Staff Engineer at Pinterest) describes how he started a voluntary #how-i-ai Slack channel that organically grew to 1,200+ members across functions. This led to a formal company-wide 'AI…

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