Remote Software Engineer (Staff-Level)

Description:

• Chestnut is building the first AI-native operating system for insurance distribution, transforming how the $1T+ insurance industry allocates its largest spend: sales and distribution.
• The company is backed by a16z and aims to replace legacy systems with a modern, flexible platform that helps carriers automate complex workflows, optimize distribution spending, and unlock new growth.
• Chestnut has major insurers under contract and is experiencing expansion with early adopters.
• The company believes in small, high-context teams using best-in-class tools to achieve significant results and aims for 10x productivity gains.
• The role of Software Engineer involves modernizing the infrastructure of the insurance industry, contributing to core product experiences, and laying the groundwork for intelligent automation.
• The engineering team is focused on building modern infrastructure for AI-driven insurance operations, including well-structured data models, real-time event pipelines, clean APIs, and usable tools.
• As a Software Engineer, you will join a cross-functional team to deliver impactful features quickly, work across the stack, contribute to system design, and help shape the technical culture.

Requirements:

• You should have 8+ years of experience building and scaling complex software systems.
• You must have led architecture or technical strategy for a product or platform team.
• You should be comfortable working across backend, data, and infrastructure layers, and be willing to dive into frontend when necessary.
• You need to think in systems and excel at finding pragmatic solutions to complex problems.
• You should be excited to shape the technical direction of a growing company.
• Strong communication skills and the ability to work across disciplines are essential.
• You should be energized by ambiguity, real-world data, and building for scale.

Benefits:

• The position offers a competitive salary and equity, with a 10-year exercise window for stock options.
• Chestnut promotes a remote-first culture built on trust, autonomy, and high performance.
• The company organizes team offsites to foster bonding among employees.
• There is a "take what you need" vacation policy to support work-life balance.
• Employees receive top-notch health, dental, and vision insurance, which is subsidized by the company.