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The Director of Underwriting leads Thimble's underwriting operations, focusing on developing and implementing underwriting guidelines, ensuring compliance, assisting with claims, and monitoring underwriting risk. The role aims to enhance product offerings, grow the small-to-medium business market, and maintain acceptable underwriting profit while supporting the company's mission.

The VP of Product will lead Thimble's Product Team, responsible for developing and executing a roadmap for insurance solutions. This role involves managing product deliverables, guiding the team through strategic product decisions, and ensuring alignment with organizational objectives. Leadership, negotiation, and a proactive approach to decision-making are key aspects of this position.