Arvind Jain couldn't find his own company's data at Rubrik. So in 2019 before ChatGPT, before the AI boom, he built Glean, the first enterprise generative AI company. Now they're doubling past $100M ARR with 1,100 employees and watching tech giants copy their playbook. But Jain admits his biggest mistake: being too conservative. "We should have gone much bigger, much faster," he says, crediting his Indian upbringing for the cautious approach. Still, Glean remains years ahead as competitors scramble to build "AI that knows your company's data." His contrarian take on AI? It won't shrink workforces, it'll just raise the bar for everyone. The real edge isn't the technology; it's execution. And despite the relentless pace keeping him up at night, Jain's never been more optimistic about building a multi-billion dollar business.
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