Chestnut

Lead QA strategy, build automation frameworks, integrate QA into SDLC, and manage quality metrics and defect tracking. | 5+ years QA experience with 2+ years in lead role, proficiency in modern test frameworks and scripting, strong communication, and experience building automation from scratch. | About Chestnut 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. Backed by a16z, we're replacing legacy systems with a modern, flexible platform that helps carriers automate complex workflows, optimize every distribution dollar, and unlock new growth. We have major insurers under contract, and early adopters are expanding. This is a generational platform shift. Recent advances in agentic AI make it possible to automate what was once manual and error-prone. We've spent years building the data model and context layer required to make this real, and now we're scaling with urgency. At Chestnut, we operate with the belief that small, high-context teams working with best-in-class tools and colleagues can achieve outsized results. We embody what it means to be AI-lean: chasing 10x productivity gains that allow us to scale impact beyond our headcount. If you're excited to modernize the infrastructure of one of America's most essential industries, we'd love to meet you. Whether shaping core product experiences or laying the groundwork for intelligent automation, your work will accelerate a once-in-a-generation transformation. Job Description We're looking for a QA Lead Software Engineer to be our first QA hire and lay the foundation for quality engineering across the company. This is a hands-on, high-impact role where you'll define what QA looks like at Chestnut - from strategy to tooling to team growth. You'll build our first test automation framework, champion quality across the stack, and play a key role in scaling our platform. What You'll Do • Build Chestnut's QA strategy, tools, and processes from the ground up • Design and implement an automated test framework (we use Playwright + TypeScript) • Define what should be automated - and what shouldn't • Work closely with engineering and product to integrate QA into our SDLC • Own quality metrics, test plans, and defect tracking • Set the stage for future QA team growth What We're Looking For • 5+ years in QA, including 2+ years in a lead or founding QA role • Strong with modern test frameworks (e.g., Playwright, Cypress, Selenium) • Proficient in scripting (TypeScript, Python) and familiar with CI/CD pipelines • Excellent communicator who can work cross-functionally and independently • Experience building automation frameworks or processes from scratch • Bonus Points • Experience testing APIs and backend systems • Familiarity with cloud platforms (AWS, GCP, Azure) • Mobile testing experience You'll be joining a small, fast-moving team backed by top-tier investors (including a16z) and working on a product that's transforming how insurance carriers operate. Apply now to help define and lead QA at Chestnut. 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

As a Software Engineer, you will build the backbone of an AI-native platform, working on services, workflows, and user interfaces. You will own your work from architecture to deployment and help shape the technical culture. | Candidates should have 3-5+ years of experience building production systems with Go, TypeScript, and React. Strong CS fundamentals and hands-on experience with modern orchestration tools are also required. | About Chestnut 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. Backed by a16z, we’re replacing legacy systems with a modern, flexible platform that helps carriers automate complex workflows, optimize every distribution dollar, and unlock new growth. We have major insurers under contract, and early adopters are expanding. This is a generational platform shift. Recent advances in agentic AI make it possible to automate what was once manual and error-prone. We’ve spent years building the data model and context layer required to make this real, and now we’re scaling with urgency. At Chestnut, we operate with the belief that small, high-context teams working with best-in-class tools and colleagues can achieve outsized results. We embody what it means to be AI-lean: chasing 10x productivity gains that allow us to scale impact beyond our headcount. If you’re excited to modernize the infrastructure of one of America’s most essential industries, we’d love to meet you. Whether shaping core product experiences or laying the groundwork for intelligent automation, your work will accelerate a once-in-a-generation transformation. Engineering at Chestnut We’re building the modern infrastructure for AI-driven insurance operations. That means well-structured data models, real-time event pipelines, clean APIs, and usable tools that support humans and agents working in parallel. As a Software Engineer at Chestnut, you’ll join a high-agency, cross-functional team focused on delivering impactful features fast. You’ll work across the stack, contribute to system design, and help shape the technical culture as we grow. What You’ll Do Build the backbone of our AI-native platform — from Go services and event-driven workflows to React UIs and automation layers Work closely with product and design to ship fast, learn quickly, and iterate on high-impact features Own your work end-to-end — from architecture to deployment, with clear handoffs and strong accountability Scale our foundation — shaping infrastructure like observability, permissions, and dev tooling Move like a builder: stay unblocked, act with urgency, and focus on what matters most You Might Be a Fit If You… Have 3–5+ years building and scaling production systems with Go, TypeScript, and React Strong CS fundamentals - you design thoughtfully and build systems that last Have hands-on experience with gRPC, event-driven architecture, and clean, versioned APIs Are fluent in containers and modern orchestration tools like Temporal, Dagster, and ArgoCD Thrive in fast-paced, high-agency environments and know how to navigate tradeoffs Are curious about AI, drawn to complexity, and motivated to shape foundational systems in a massive industry Our Stack Languages: Go, TypeScript Frontend: React, Tailwind Infra: K8s, ArgoCD, Kargo, Temporal, Dagster Data: Postgres, Dynamo, Snowflake 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

Lead the design and development of core systems, ensuring long-term scalability and reliability. Partner cross-functionally to scope, prioritize, and deliver high-impact features that drive real business outcomes. | Candidates should have 5-8 years of experience building and scaling production systems and thrive in early-stage environments. They should write clean, maintainable code and take ownership while being energized by real-world complexity and automation. | About Chestnut 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. Backed by a16z, we’re replacing legacy systems with a modern, flexible platform that helps carriers automate complex workflows, optimize every distribution dollar, and unlock new growth. We have major insurers under contract, and early adopters are expanding. This is a generational platform shift. Recent advances in agentic AI make it possible to automate what was once manual and error-prone. We’ve spent years building the data model and context layer required to make this real, and now we’re scaling with urgency. At Chestnut, we operate with the belief that small, high-context teams working with best-in-class tools and colleagues can achieve outsized results. We embody what it means to be AI-lean: chasing 10x productivity gains that allow us to scale impact beyond our headcount. If you’re excited to modernize the infrastructure of one of America’s most essential industries, we’d love to meet you. Whether shaping core product experiences or laying the groundwork for intelligent automation, your work will accelerate a once-in-a-generation transformation. Engineering at Chestnut We’re building the modern infrastructure for AI-driven insurance operations. That means well-structured data models, real-time event pipelines, clean APIs, and usable tools that support humans and agents working in parallel. As a Software Engineer at Chestnut, you’ll join a high-agency, cross-functional team focused on delivering impactful features fast. You’ll work across the stack, contribute to system design, and help shape the technical culture as we grow. What You’ll Do Lead the design and development of core systems - from Go microservices and event-driven workflows to React UIs and automation layers Partner cross-functionally to scope, prioritize, and deliver high-impact features that drive real business outcomes Own architecture and implementation decisions end-to-end, ensuring long-term scalability and reliability Contribute to and evolve core infrastructure, including observability, permissions, and developer experience Set the bar for technical excellence - mentoring teammates, improving processes, and helping us scale with confidence You Might Be a Fit If You… Have 5-8 years of experience building and scaling production systems Thrive in early-stage environments and enjoy wearing many hats Write clean, maintainable code and care about craftsmanship Think in systems and design with an eye toward flexibility and resilience Take ownership, act with urgency, and bias toward progress over perfection Are energized by real-world complexity, data modeling, and automation Want to help define the future of engineering at Chestnut Our Stack Languages: Go, TypeScript Frontend: React, Tailwind Infra: K8s, ArgoCD, Kargo, Temporal, Dagster Data: Postgres, Dynamo, Snowflake 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

Lead the design and implementation of critical systems for the platform. Make architectural decisions that optimize for scale, performance, and maintainability. | Have 8+ years of experience building and scaling complex software systems. Are comfortable working across backend, data, and infrastructure layers. | About Chestnut 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. Backed by a16z, we’re replacing legacy systems with a modern, flexible platform that helps carriers automate complex workflows, optimize every distribution dollar, and unlock new growth. We have major insurers under contract, and early adopters are expanding. This is a generational platform shift. Recent advances in agentic AI make it possible to automate what was once manual and error-prone. We’ve spent years building the data model and context layer required to make this real, and now we’re scaling with urgency. At Chestnut, we operate with the belief that small, high-context teams working with best-in-class tools and colleagues can achieve outsized results. We embody what it means to be AI-lean: chasing 10x productivity gains that allow us to scale impact beyond our headcount. If you’re excited to modernize the infrastructure of one of America’s most essential industries, we’d love to meet you. Whether shaping core product experiences or laying the groundwork for intelligent automation, your work will accelerate a once-in-a-generation transformation. Engineering at Chestnut We’re building the modern infrastructure for AI-driven insurance operations. That means well-structured data models, real-time event pipelines, clean APIs, and usable tools that support humans and agents working in parallel. As a Software Engineer at Chestnut, you’ll join a high-agency, cross-functional team focused on delivering impactful features fast. You’ll work across the stack, contribute to system design, and help shape the technical culture as we grow. What You’ll Do Lead the design and implementation of critical systems that serve as building blocks for the platform Make architectural decisions that optimize for scale, performance, and maintainability Partner with product, design, and other engineering leaders to define roadmaps and scope technical investments Identify and unblock high-risk areas across teams, diving deep when needed Raise the bar for engineering excellence through mentorship, modeling, and thoughtful code review Help establish engineering culture, norms, and hiring standards as we grow You Might Be a Fit If You… Have 8+ years of experience building and scaling complex software systems Have led architecture or technical strategy for a product or platform team Are comfortable working across backend, data, and infra layers (and diving into frontend when needed) Think in systems and excel at finding pragmatic solutions to messy problems Are excited to shape the technical direction of a growing company Have strong communication skills and enjoy working across disciplines Are energized by ambiguity, real-world data, and building for scale Our Stack Languages: Go, TypeScript Frontend: React, Tailwind Infra: K8s, ArgoCD, Kargo, Temporal, Dagster Data: Postgres, Dynamo, Snowflake 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