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Building Cursor: A Fireside Chat with VP Solutions Ricky Doar

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Nov 27, 2025
Ricky Doar, VP of Solutions at Cursor, brings a wealth of experience from leading AI developer tool implementations. He discusses AI as a learnable engineering skill and emphasizes the importance of understanding model capabilities. Ricky warns against over-reliance on AI for strategic decisions and highlights best practices for working with existing codebases. He also shares insights on managing context windows and when to trust AI suggestions, ultimately guiding engineers to make informed decisions while harnessing AI's potential.
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INSIGHT

Think Alongside The Model

  • Working with AI is a new, adjacent skill to engineering that requires learning how to think alongside models.
  • Top users break big problems into bite-sized tasks that match model capabilities to reduce hallucination.
ADVICE

Build A Model Barometer

  • Get familiar with each model's strengths, weaknesses, and personality before trusting it with big tasks.
  • Iteratively test tasks to build an internal barometer of what size problems the model can reliably solve.
ADVICE

Stay Responsible For Architecture

  • Stay in the driver's seat and don't offload strategic or architectural decisions to the AI.
  • Use Cursor to ramp up on a codebase, but always validate and understand AI-generated choices.
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