#222 - Closing the Knowledge Gap in Your Legacy Code with AI - Omer Rosenbaum

44 snips

Jun 30, 2025

Omer Rosenbaum, CTO and co-founder of Swimm, shares insights on closing the knowledge gap in legacy code using AI. He discusses the importance of human oversight when employing AI, highlighting its limitations in understanding complex systems. Omer emphasizes the critical role of documentation, especially for junior developers navigating the AI landscape, and warns against over-reliance on AI tools. He offers practical advice for conducting effective research in tech organizations, stressing the balance between leveraging AI and maintaining contextual knowledge.

Ask episode

AI Snips

Chapters

Books

Transcript

Episode notes

ANECDOTE

Early Tech Training Influenced Career

Omer trained in a special tech unit before university, gaining intense hands-on learning and interest in teaching.
This practical start gave him broad interdisciplinary university studies and teaching experience across locations, influencing his career.

ADVICE

Juniors Must Understand AI Code

Junior developers must learn to use AI effectively but avoid shipping code they don't fully understand.
They should explain tasks clearly and review AI outputs critically to grow and avoid critical bugs.

INSIGHT

AI's Impact on Critical Thinking

AI can either improve or reduce our critical thinking depending on our response to errors.
If users become more willing to verify AI outputs after failures, AI may enhance critical thinking.

Get the Snipd Podcast app to discover more snips from this episode

Get the app

What if your most critical systems run on code that no one fully understands?

In this episode, Omer Rosenbaum, CTO and co-founder of Swimm, explains how to use AI to close the knowledge gap in your legacy codebase. Discover the limitations of AI in understanding legacy code and learn novel approaches to automatically document complex systems, ensuring their critical business logic is preserved and understood within the organization. Beyond legacy systems, Omer also shares practical advice for how junior developers can thrive in the AI era and how teams and organizations can conduct more effective research.

Key topics discussed:

How junior developers can thrive in the age of AI
The danger of shipping code you don’t fully understand
Why AI can’t deduce everything from your code alone
How writing documentation becomes more critical now with AI
How to analyze code that even LLMs struggle to read, like COBOL
How to keep your organization’s knowledge base trustworthy and up to date
The real danger of letting AI agents run unchecked
A practical approach to conducting more effective research

Timestamps:

(00:00) Trailer & Intro
(02:10) Career Turning Points
(05:24) What Juniors Should Do in the Age of AI
(11:05) Junior Developer’s Responsbility When Using AI
(14:50) AI and Critical Thinking
(16:20) Understanding & Preserving Domain Knowledge
(18:11) The Importance of Written Knowledge for AI Usage
(21:51) Limitations of AI in Understanding Knowledge Base
(26:34) The Limitations of LLM in Navigating Legacy Codebases (e.g. COBOL)
(32:38) Effective Knowledge Sharing Culture in the Age of AI
(34:54) Keeping Knowledge Base Up-to-Date
(36:55) Keeping the Organization Knowledge Base Accurate
(39:08) Fact Checking and Preventing AI Hallucination
(41:24) The Potential of MCP
(43:24) The Danger of AI Agents Hallucinating with Each Other
(45:00) How to Get Better at Research
(53:41) The Importance of Investing in Research
(57:18) 3 Tech Lead Wisdom

_____

Omer Rosenbaum’s Bio
Omer Rosenbaum is the CTO and co-founder of Swimm, a platform reinventing the way engineering organizations manage internal knowledge about their code base. Omer founded the Check Point Security Academy and was the Cyber Security Lead at ITC, an educational organization that trains talented professionals to develop careers in technology. Omer has a MA in Linguistics from Tel Aviv University and is the creator behind the Brief YouTube Channel.

Follow Omer:

LinkedIn – linkedin.com/in/omer-rosenbaum-034a08b9
Twitter – x.com/Omer_Ros
Swimm – swimm.io
Email – omer@swimm.io
📚 Gitting Things Done – buymeacoffee.com/omerr/extras
▶️ Brief – youtube.com/@BriefVid

Like this episode?
Show notes & transcript: techleadjournal.dev/episodes/222.
Follow @techleadjournal on LinkedIn, Twitter, and Instagram.
Buy me a coffee or become a patron.