Forward Deployed Product Manager

Remote. Posted 7 months ago

The role

You will own customer relationships and drive the success of forward deployments end-to-end. You will embed with customers to understand workflows and lead the transformation of distribution operations using the platform.

What you will do

Own the customer relationship from kickoff through deployment and beyond.
Lead discovery and workflow mapping to identify automation and AI transformation opportunities.
Build end to end to deliver closed-loop customer value including migration scripts, data schema maps, feature extensions, and bug fixes.
Drive execution in partnership with engineering and design.
Test edge cases, debug issues, and push the product forward.
Run tight deployments by managing timelines and influencing customer stakeholders.
Identify repeatable patterns and surface opportunities for AI-native features.

Required qualifications

5+ years of experience in roles like product manager, technical product manager, founder, consultant, or engagement lead.
Have shipped a migration, cutover, or integration.
Communicate clearly written and verbal.
Align teams around a vision and drive execution without waiting for perfect inputs.
Adaptable in personal workflows and eager to re-adapt along with shifts in AI tooling landscape.
Relentlessly curious.

Nice to have

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
Take what you need vacation policy
Top notch health, dental, and vision insurance subsidized by us

About the company

Chestnut is building the AI-native operating system for insurance distribution. They are replacing legacy systems with a modern platform that allows carriers to automate workflows, optimize distribution spend, and unlock new growth.