Growing Software: Using AI for Digital Cultivation by Dylan Isaac

Presentation Description

What if building software with AI wasn’t about commanding a tool, but cultivating a living system? In this talk, Dylan Isaac shares how developing with AI mirrors the ancient art of bonsai—requiring vision, constraints, and gentle guidance rather than rigid control.

You’ll discover how to:
– Set “constraints” (tech stack, frameworks, tests) that guide AI growth like a bonsai pot
– Use prompts as “stakes and wires” to shape development while letting the AI express what it knows best
– Balance your mind’s eye vision with the AI’s organic capabilities
– Iterate through feedback loops like a gardener tending their craft

Through practical examples of team automation, documentation generation, and progressive AI systems, you’ll learn to work with AI’s probabilistic nature rather than fighting it.

Presentation Details

Date:
11/09/2025
Time:
10:00 AM
Location:
Downstairs Classroom

Presenter Biography

Dylan Isaac
Dylan Isaac (he/they) is an engineer, designer, and accessibility advocate who combines technical rigor with a human-centered ethos. After years advancing web accessibility at Deque Systems, Dylan founded Enablement Engineering, a consultancy dedicated to building “ladders, not walls” through open-source AI systems and transparent design. Currently serving as a Digital Accessibility AI Engineer with the University of Illinois Chicago, Dylan leads development of an AI-driven PDF-to-accessible-HTML pipeline—integrating multi-agent workflows, semantic caches, and educator oversight to reimagine how academic content becomes accessible. Their work spans LLM-powered remediation, intention-driven automation, and design systems that adapt technology to people—not the other way around. Dylan is known for weaving together philosophy, accessibility, and AI with humor and clarity.
Dylan Isaac (white male with a beard) smiling outdoors in front of a sunlit mountain landscape, wearing a dark hoodie.