Sierra

Brett Taylor has spent his career building category-defining products—from Google Maps to the social features that became hallmarks of modern social media. After stints as CTO of Facebook and co-CEO of Salesforce, he found himself at OpenAI as chairman of the board, watching the evolution of AI capabilities firsthand. The conviction crystallized: the entire software market is shifting toward AI agents and outcome-based pricing. "The whole market is going to go towards agents," Brett said in a recent podcast appearance. "I think the whole market is going to go towards outcomes based pricing. It's just so obviously the correct way to build and sell software."

With that thesis in mind, he launched Sierra to build agents that can handle customer service, sales, and other enterprise functions. It's a natural extension of his product philosophy: identify where technology can create fundamentally new experiences, not just digitize what came before.

The details on Sierra's early development remain sparse in available sources, but Taylor's approach is informed by hard-won lessons from decades of building. At FriendFeed, his early startup, he learned that polishing a product in isolation isn't enough—distribution and market timing matter as much as features. That company, which invented the like button and real-time news feeds, was ultimately outmaneuvered by Twitter not because the product was worse, but because Twitter focused relentlessly on celebrity adoption while FriendFeed stayed focused on product perfection.

Taylor has also internalized the importance of challenging your own assumptions. Early in his career at Google, he built Google Local—a me-too version of Yahoo Yellow Pages grafted onto search results. Despite a link on the Google homepage, it flopped. The product was fine, but it wasn't differentiated. That failure led to a reframing: instead of digitizing Yellow Pages, what if you made the map the canvas? That insight eventually became Google Maps, which got 10 million users on day one and 90 million users the day satellite imagery launched.

Taylor's operating philosophy—"What is the most impactful thing I could do today?"—informs how he thinks about building and scaling. This mindset, crystallized through a conversation with Sheryl Sandberg when he was CTO at Facebook, helped him understand that your natural strengths can become blinders. Engineers default to engineering solutions. Product people default to redesigns. Founders often pursue solutions that play to their superpower rather than the company's actual need.

For Sierra, the thesis is clear: AI agents represent a new computing paradigm, and the companies that build the best agents will define the next era of software. Taylor also believes the industry is sleeping on how transformative agents will be for business operations, particularly in high-touch functions like customer service and sales.

Sierra is positioned as Brett Taylor's latest venture, combining his product acumen with his conviction about AI's trajectory. While specific traction metrics aren't publicly available, the company has the advantage of a founder who has repeatedly built category-defining products, navigated acquisitions, and scaled teams at the highest levels of the tech industry. Taylor's board seat at OpenAI gives him visibility into frontier AI capabilities and helps inform Sierra's product direction. In a market flooded with AI startup noise, Sierra stands out as the vehicle of a builder who has proven he can identify which technologies will actually reshape how people work.