Chestnut · 5 months ago
Product & Commercial Lead
United States
Full-time
Remote
Senior Level
5+ years expChestnut is building an AI-native operating system for insurance distribution, aiming to transform the $1T+ insurance industry. As a Product & Commercial Lead, you will own customer relationships and drive the success of deployments, blending product thinking with execution to deliver measurable impact.
Financial ServicesSmall and Medium BusinessesSoftware
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
Qualification
Required
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
Preferred
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
Company
Chestnut
Purpose-made producer management and compensation system for insurance carriers and their distribution partners.
11-50 employees
H1B Sponsorship
Chestnut has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (1)
2023 (1)
Funding
Current Stage
Early StageTotal Funding
unknown2022-03-25Seed
Leadership Team
David Zhang
CEO & Co-Founder
Recent News
Andreessen Horowitz
2026-01-20
chestnutfi.com
2026-01-20
Company data provided by crunchbase