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The Bottom-Up Adoption Journey: How AI Is Reshaping Our Roles, Org, Workflows & Culture

Posted Oct 01, 2025 | Views 8
# AI
# Change Management
# Workflows
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Randall Tombaugh
Engineering Leadership @ WorkOS

Randall is part of the engineering leadership at WorkOS, a modern platform that helps developers quickly build and ship enterprise-ready features. Beyond overseeing the company’s design system and UI surfaces, he focuses on hiring, growing culture, and mentoring leaders across all of engineering. His team also maintains the open-source Radix UI framework.

Previously, Randall was Head of Engineering at Droplet, a low-code solution for forms and workflow automation. He began his engineering career at Microsoft, contributing to the .NET platform and later Azure, and has been leading engineering teams since his time at Auth0 nearly a decade ago. Randall lives in Honolulu, Hawaii with his family, where he has been working remotely for nearly as long.

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SUMMARY

Slide deck available here: https://docs.google.com/presentation/d/1Y-FGLBs1K4F3nn21dn5kzEYzE_jnYcJYQ0uqMyT-ev0/preview?slide=id.g37c8a22c173_1_0

This session explores how AI is reshaping engineering organizations from the bottom up. Drawing on real examples from WorkOS, we’ll look at different engineering personas, how their motivations shape their response to AI, and the cultural and structural pressures that follow. You’ll leave with a practical framework for understanding AI’s impact on your teams and strategies for creating the conditions where bottom-up evolution can thrive.

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