Product & Commercial Lead

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 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.

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.

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.

You Could Be a Great Fit If You...

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.

Bonus

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