Forward Deployed Engineer (Entry-Level / Early Career)
Job Description:
• Chestnut is building the first AI-native operating system for insurance distribution by transforming how the $1T+ insurance industry allocates its largest spend: sales and distribution.
• We’re replacing legacy systems with a modern, flexible platform that helps carriers automate complex workflows, optimize every distribution dollar, and unlock new growth.
• Recent advances in agentic AI make it possible to automate what was once manual and error-prone.
• We operate with the belief that small, high-context teams working with best-in-class tools can achieve outsized results.
• If you’re excited to modernize the infrastructure of one of America’s most essential industries, we’d love to meet you.
• We’re building the modern infrastructure for AI-driven insurance operations with well-structured data models, real-time event pipelines, clean APIs, and usable tools.
• As a Software Engineer at Chestnut, you’ll join a high-agency, cross-functional team focused on delivering impactful features fast.
Requirements:
• 0–2 years experience, with solid coding fundamentals (Python, Go, or TypeScript ideal)
• Curious, resourceful, and biased toward action—you’re not afraid to figure things out
• Interest in applied AI—whether it’s workflow automation, data enrichment, or retrieval-augmented generation
• Strong communicator who wants to understand both the tech and the business
• Comfortable with ambiguity, eager to learn from others, and motivated to own real problems
• Willingness to travel up to 25% for high-leverage, in-person work
• Bonus: experience with LLMs, open-source AI tools, or side projects that shipped
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
Apply tot his job
Apply To this Job
• Chestnut is building the first AI-native operating system for insurance distribution by transforming how the $1T+ insurance industry allocates its largest spend: sales and distribution.
• We’re replacing legacy systems with a modern, flexible platform that helps carriers automate complex workflows, optimize every distribution dollar, and unlock new growth.
• Recent advances in agentic AI make it possible to automate what was once manual and error-prone.
• We operate with the belief that small, high-context teams working with best-in-class tools can achieve outsized results.
• If you’re excited to modernize the infrastructure of one of America’s most essential industries, we’d love to meet you.
• We’re building the modern infrastructure for AI-driven insurance operations with well-structured data models, real-time event pipelines, clean APIs, and usable tools.
• As a Software Engineer at Chestnut, you’ll join a high-agency, cross-functional team focused on delivering impactful features fast.
Requirements:
• 0–2 years experience, with solid coding fundamentals (Python, Go, or TypeScript ideal)
• Curious, resourceful, and biased toward action—you’re not afraid to figure things out
• Interest in applied AI—whether it’s workflow automation, data enrichment, or retrieval-augmented generation
• Strong communicator who wants to understand both the tech and the business
• Comfortable with ambiguity, eager to learn from others, and motivated to own real problems
• Willingness to travel up to 25% for high-leverage, in-person work
• Bonus: experience with LLMs, open-source AI tools, or side projects that shipped
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
Apply tot his job
Apply To this Job