It started as a college kid's fix for a boring problem: where do you put your files? Two decades later, Box holds the paperwork for most of the Fortune 500 - and is teaching that paperwork to think.

Conga, Twilio, Broadridge, Newgen, Hyland and Templafy now compete on the systems around a document - data, delivery, governance and AI. The right choice begins with the job, not the feature list.

ReadMe, KMS Lighthouse, MadCap Software and Microsoft are turning documentation from a reference shelf into a working layer for AI. The useful question is no longer which tool stores the most, but which kind of knowledge your business needs to move.

Two Denver software companies are attacking the same expensive problem from opposite ends: MadCap prepares governed content for machines, while Spekit puts approved answers inside the work itself.

Hiten Shah is a serial SaaS entrepreneur, angel investor, and startup advisor who co-founded KISSmetrics, Crazy Egg, Nira (acquired by Dropbox in 2024), and Product Habits. Over 20+ years, he has built and scaled multiple companies using a philosophy of radical customer obsession, clarity of communication, and deliberate execution. He advises 120+ startups, has invested in 25+ companies, and shares insights through his newsletter, The Startup Chat podcast, and a 272K+ following on X.