Fidji Simo, OpenAI’s No. 2 executive, is stepping down from her full-time role due to an extended medical leave for a neuroimmune condition relapse, creating a leadership void right as the company eyes a potential IPO and struggles to close the enterprise gap with Anthropic. Simo had been widely seen as a future CEO candidate once OpenAI went public, making this a critical gap for Sam Altman to fill. The departure compounds recent exits: CMO Kate Rouch left for cancer recovery, CPO Kevin Weil also departed, and COO Brad Lightcap moved into a special projects role earlier this year.

Google is rolling out a new consumer-facing feature in My Ad Center that will indicate when an ad has been created or edited with AI. The disclosure is automatic for ads made using Google's own generative AI tools, but for other ads, advertisers must self-report and Google will not perform its own check. This extends AI ad transparency beyond election ads, revealing both progress and the limitations of voluntary enforcement.

Lovable is reportedly doubling its valuation to $13.2 billion with a $300 million raise led by Menlo Ventures, riding the hottest trend in AI: vibe coding. The article provides a useful snapshot of a market where startups like Replit and Cursor are seeing massive valuations, suggesting the category is consolidating fast but also testing the limits of investor faith in unproven business models.