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Bret Taylor’s Sierra reaches $100M ARR in under two years; also, Phictly’s new app brings people together over their favorite books and TV shows

Nov 24, 2025
Sierra achieves an astonishing $100 million ARR in under two years, showcasing the swift adoption of AI customer service solutions by enterprises. Meanwhile, Phictly is revolutionizing fan communities with its app, creating cozy spaces for book and TV show enthusiasts. The app boasts features like capped club sizes and spoiler-free environments, perfect for those who crave thoughtful discussions without interruptions. Nalina Aiken's personal journey inspired Phictly, aiming to simplify scheduling for intimate group engagements.
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INSIGHT

Enterprise Embrace Of AI Agents

  • Sierra reached $100M ARR in under two years, signaling rapid enterprise adoption of AI agents.
  • The company charges per completed work and achieved a 100x revenue multiple on fast growth.
ANECDOTE

Founders Surprised By Customer Mix

  • Bret Taylor and Clay Baver said they were surprised by Sierra's growth speed.
  • They expected tech firms to adopt agents first but were astounded older businesses also became customers.
INSIGHT

Automation Of Complex Customer Tasks

  • Sierra automates tasks like patient authentication, returns, and mortgage help, replacing many human customer service tasks.
  • Outcomes-based pricing ties revenue to completed work rather than flat subscriptions.
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