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ChestnutChestnutUnited States

Product & Commercial Lead

Leads customer relationships and deployments for AI-native insurance platform, mapping workflows, prototyping solutions with engineers/designers, and driving product improvements for measurable business impact. Requires 5+ years in product/consulting roles with technical acumen.

Salary not listed
Remote5+ YOESolutions Architecture

About the role

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

Skills

APIsSQLInternal ToolsEnterprise WorkflowsAI AutomationProduct FeaturesData Systems

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