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October 4, 2025
On October 3, we hosted a live workshop with Nivedha Venkatesh, CEO and co-founder of Pageloop, on how startups can design knowledge bases that evolve alongside their products. Our conversation explored why documentation is no longer just an afterthought, but the connective tissue between teams, customers, and increasingly, AI systems.
Nivedha emphasized that even in the earliest stages of a company, documentation prevents silos and reduces repetitive questions. At Pageloop, engineers are expected to update docs every time they ship: not only to keep teammates aligned, but also to build empathy for customers who rely on those docs to understand new features.
A recurring theme was the balance between human readability and AI usability. Documentation today isn’t just read by customers or teammates, it’s ingested by LLMs powering support chatbots and search. That means headings, subheadings, and alt text aren’t just nice-to-haves, they’re essential for both accessibility and machine parsing.
While screenshots are increasingly well-handled by multimodal models, GIFs and videos remain problematic. Nivedha cautioned that relying solely on visuals without accompanying text risks losing meaning for AI systems. The best approach is to pair visuals with good alt-text captions and clear explanations. That way, humans can skim the images, but LLMs still have structured context to pull from.
Audience questions sparked discussion about AI-generated docs. While LLMs can accelerate drafting, Nivedha stressed the need for human review. Just as developers use plan mode in Cursor or Claude Code to check code before execution, documentation teams must validate AI-written content to ensure accuracy and trust.
Good documentation isn’t just external-facing. It’s also a cornerstone for onboarding and training. Instead of bogging down senior employees with repetitive Slack questions, teams can invest in knowledge bases that scale culture and processes. With LLM-assisted tools like voice-to-doc workflows, internal documentation is easier to produce than ever.
One challenge is ownership. Historically, docs have floated between product, support, and growth. Nivedha noted a shift: support teams and CEOs are increasingly taking the lead, driven by two forces:
Looking forward, Nivedha highlighted three big shifts:
A huge thank you to Nivedha for sharing her insights, and to everyone who joined us live.