Rupa Parameswaran, VP of Security & IT at Handshake, tackles AI security by starting with mapping happy paths: document every legitimate route for accessing, adding, moving, and removing your crown jewels, then flag everything outside those paths. When vendors like ChatGPT inadvertently get connected to an entire workspace instead of individual accounts (scope creep that she's witnessed firsthand), these baselines become your detection layer. She suggests building lightweight apps that crawl vendor sites for consent and control changes, addressing the reality that nobody reads those policy update emails.

Rupa also reflects on the data labeling bottlenecks that block AI adoption at scale. Most organizations can't safely connect AI tools to Google Drive or OneDrive because they lack visibility into what sensitive data exists across their corpus. Regulated industries handle this better, not because they're more sophisticated, but because compliance requirements force the discovery work. Her recommendation for organizations hitting this wall is self-hosted solutions contained within a single cloud provider rather than reverting to bare metal infrastructure. The shift treats security as quality engineering, making just-in-time access and audit trails the default path, not an impediment to velocity.

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