Product & Commercial Lead

Summary

Join Chestnut, a company building an AI-native operating system for insurance distribution, as their Product & Commercial Lead. In this role, you will own customer relationships and drive the success of Chestnut’s forward deployments. You will embed with customers, understand their workflows, and lead the transformation of their distribution operations using Chestnut’s platform. This position blends product thinking, execution, and customer partnership, requiring you to identify gaps, prototype solutions, and collaborate with engineers and designers. You will manage timelines, influence stakeholders, and identify opportunities for platform development and AI automation. You will be responsible for driving key outcomes in commercial operations and helping the company move faster and deliver measurable impact. The ideal candidate is curious, autonomous, relentless, and eager to work with imperfect information.

Requirements

• Have 5+ years of experience in roles like product manager, consultant, investor, founder, or engagement lead
• Bring strong technical acumen and can reason through complex systems and data
• Communicate clearly and build trust across technical and non-technical stakeholders
• Know how to align teams around a vision and drive execution without waiting for perfect inputs
• Are relentlessly curious – you learn fast, ask thoughtful questions, and dive deep when it matters
• Care about solving real business problems and turning customer pain into product features

Responsibilities

• Own the customer relationship from kickoff through deployment and beyond. Act as the point of accountability and a trusted partner in delivering measurable business value
• Lead discovery and workflow mapping to understand org structures, pinpoint pain, and identify the highest-leverage opportunities for automation and AI transformation
• Drive execution in partnership with engineering and design - translating insights into high-impact product features and platform improvements
• Get in the weeds to ensure quality. Test edge cases, debug issues, and push the product forward with urgency and precision
• Run tight deployments by managing timelines, unblocking bottlenecks, and influencing customer stakeholders to ensure successful outcomes
• Bridge product and market by identifying repeatable patterns, surfacing opportunities for AI-native features, and shaping the evolution of our platform

Preferred Qualifications

• Experience with APIs, internal tools, or complex enterprise workflows
• Background in insurance, finance, or regulated industries
• Ability to write SQL or work with large datasets

Benefits

• Competitive salary and equity, with 10 year exercise window for stock options
• Remote-first culture built on trust, autonomy, and high performance
• Team offsites for all of us to bond
• Take what you need vacation policy
• Top notch health, dental, and vision insurance subsidized by us