Product & Commercial Lead

Chestnut is building the first AI-native operating system for insurance distribution by transforming how the $1T+ insurance industry allocates its largest spend: sales and distribution.

Backed by a16z, we’re replacing legacy systems with a modern, flexible platform that helps carriers automate complex workflows, optimize every distribution dollar, and unlock new growth. We have major insurers under contract, and early adopters are expanding.

This is a generational platform shift. Recent advances in agentic AI make it possible to automate what was once manual and error-prone. We’ve spent years building the data model and context layer required to make this real, and now we’re scaling with urgency.

At Chestnut, we operate with the belief that small, high-context teams working with best-in-class tools and colleagues can achieve outsized results. We embody what it means to be AI-lean: chasing 10x productivity gains that allow us to scale impact beyond our headcount.

If you’re excited to modernize the infrastructure of one of America’s most essential industries, we’d love to meet you. Whether shaping core product experiences or laying the groundwork for intelligent automation, your work will accelerate a once-in-a-generation transformation.

As a Product & Commercial Lead, you are the tip of the spear, owning customer relationships and driving the success of Chestnut’s forward deployments end-to-end. You will embed with our customers, deeply understand their workflows, and lead the transformation of their distribution operations using Chestnut’s platform.

This role blends product thinking, execution, and customer partnership. You will identify gaps, prototype solutions, and work closely with forward deployed engineers and designers to turn customer-specific insights into scalable product outcomes. You’ll manage timelines, influence internal and external stakeholders, and surface opportunities for both core platform development and AI automation. Unlike a traditional PM role, you will drive key outcomes not only within the core platform, but also in commercial operations and more. Your mandate is to help us move faster, cut through complexity with clarity, and deliver measurable impact to our customers and business.

You are the founder of our customer’s success: curious, autonomous, relentless, and eager to move fast with imperfect information. You turn vague feedback into real product and help reshape how the insurance industry operates.

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  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.

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  Lead discovery and workflow mapping to understand org structures, pinpoint pain, and identify the highest-leverage opportunities for automation and AI transformation.

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  Drive execution in partnership with engineering and design - translating insights into high-impact product features and platform improvements.

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  Get in the weeds to ensure quality. Test edge cases, debug issues, and push the product forward with urgency and precision.

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  Run tight deployments by managing timelines, unblocking bottlenecks, and influencing customer stakeholders to ensure successful outcomes.

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  Bridge product and market by identifying repeatable patterns, surfacing opportunities for AI-native features, and shaping the evolution of our platform.

• 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.

• 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