Chestnut is hiring a Product & Commercial Lead to be the tip of the spear, owning customer relationships and driving the success of our forward deployments end-to-end. This role blends product thinking, execution, and customer partnership to transform customer distribution operations using our platform.
What You'll Do
- Own the customer relationship from kickoff through deployment and beyond, acting as the point of accountability and a trusted partner.
- Lead discovery and workflow mapping to understand org structures, pinpoint pain, and identify high-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 by testing edge cases, debugging issues, and pushing the product forward with urgency.
- Run tight deployments by managing timelines, unblocking bottlenecks, and influencing customer stakeholders.
- Bridge product and market by identifying repeatable patterns, surfacing opportunities for AI-native features, and shaping platform evolution.
What We're Looking For
- 5+ years of experience in roles like product manager, consultant, investor, founder, or engagement lead.
- Strong technical acumen and ability to reason through complex systems and data.
- Ability to communicate clearly and build trust across technical and non-technical stakeholders.
- Ability to align teams around a vision and drive execution without waiting for perfect inputs.
- Relentless curiosity, learning fast, asking thoughtful questions, and diving deep.
- Care about solving real business problems and turning customer pain into product features.
Nice to Have
- 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 & Compensation
- Competitive salary and equity, with a 10-year exercise window for stock options.
- Remote-first culture built on trust, autonomy, and high performance.
- Team offsites for bonding.
- Take what you need vacation policy.
- Top notch health, dental, and vision insurance subsidized by the company.
Work Mode
This is a remote-first position.
Chestnut operates 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 scaling impact beyond headcount.
