At the Sierra Ventures 20th Annual CXO Summit, Dmitry Shevelenko, Chief Business Officer at Perplexity, shared how AI is transforming the way knowledge workers interact with information.
From Search to Sidekick
For decades, AI served the supply side, optimizing ads, feeds, and recommendations for large platforms. The next chapter is about shifting that power toward the individual, giving knowledge workers intelligent tools that act as collaborators rather than intermediaries. The browser, where we spend most of our time, is becoming the new interface for this transformation.
The New Literacy: Asking Better Questions
Dmitry argued that the most valuable skill in the AI era is the ability to ask great questions. The companies that thrive will cultivate curiosity as a core capability. Building accurate AI means creating systems that show sources, prioritize transparency, and align with user intent rather than clicks or ads.
Culture Beats Committees
His advice to enterprises: cancel your AI steering groups. “Everyone’s job is to figure this out.” The most significant barrier to adoption is not access to tools but culture. The organizations that move fastest will reward employees who experiment, share what works, and help others learn.
How We Define “Real Work” in the AI Era
Dmitry challenged leaders to rethink what productivity means inside their organizations. At Perplexity, the team has eliminated internal decks and long documents. “If AI can generate it, it’s not the real work.”
Real work, he argued, is the thinking that happens before the output, the curiosity to ask sharper questions, the discipline to interpret data, and the creativity to form new hypotheses. Too often, AI is used to automate work rather than advance its purpose.
The next generation of AI-literate teams will focus less on producing artifacts and more on driving insight, alignment, and action.
The session left CXOs with a clear challenge: the future of work will depend on how well leaders empower their teams to move from links to answers, from search to curiosity, and from information consumption to insight creation.
