About Chestnut

Chestnut is building the 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 platform that allows carriers to automate workflows, optimize distribution spend, and unlock new growth. We have major fortune 500 insurers live and under contract. They’re already expanding.

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 team size.

This is especially true in this builder function, where team members are running data migration scripts and shipping production PRs. We are building an AI-driven deployment engine, bringing down the time-to-value from the industry standard of quarters to that of weeks.

If you’re excited to realize the true impact of AI in one of America’s most essential industries, we’d love to meet you. Your work will accelerate a once-in-a-generation transformation.

Product & Commercial Lead at Chestnut

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 find gaps, identify opportunities, and directly ship value to our customers. You will also turn customer insights into scalable platform products or AI workflows with engineering partners.

You’ll manage timelines, influence internal and external stakeholders. 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 and cut through complexity with clarity.

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 code changes and help reshape how the insurance industry operates.

What You’ll Do

• 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.

• Build end to end to deliver closed-loop customer value including migration scripts, data schema maps, feature extensions, bug fixes and more.

• Drive execution in partnership with engineering and design - translating insights into 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.

You Could Be a Great Fit If You...

• Have 5+ years of experience in roles like product manager, technical product manager, founder, consultant, engagement lead.

• Have shipped a migration, cutover, or integration and can tell us what broke.

• Communicate clearly written and verbal, and build trust across stakeholders.

• Align teams around a vision and drive execution without waiting for perfect inputs.

• Adaptable in your personal workflows and eager to re-adapt along with shifts in AI tooling landscape.

• Are relentlessly curious – you learn a new domain fast, ask thoughtful questions, and dive deep when it matters.

Bonus

• Background in insurance, finance, or regulated industries

• Experience with APIs, integrations and complex enterprise workflows

• Ability to understand SQL and work with large datasets

• Experience managing AI agents and automations

• Open to customer travel: 10-20%

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