Outmarket AI

Lead AI-native platform development and collaborate with founders and users to build impactful features. | Requires principal-level seniority with AI product experience and fast-paced shipping environment familiarity. | ABOUT OUTMARKET Outmarket is the AI platform for insurance, trusted by more than 250 brokerages to run the work their business depends on. Commercial insurance still runs on dense documents and slow, manual workflows, and that is exactly what we automate: quote comparisons, coverage gap and tower analysis, policy review, and proposal generation, all grounded in our customers’ own data and source-cited so teams can trust the output. The impact is concrete. Teams save 12 to 15 hours per person every week, cut errors by roughly 65 percent, and win more business, all on infrastructure that is SOC 2 Type II certified, single-tenant, and never used to train AI models. We are an AI-first company in both what we build and how we work, shipping quickly and in close partnership with the agencies that rely on us. WHAT YOU’LL GET A high-impact role with ownership from day one. Competitive compensation and meaningful equity. Direct collaboration with founders and real users. Remote-first flexibility. The opportunity to help build an AI-native product from the ground up.

Lead design, build, and operation of AI-powered features across backend and frontend, drive technical standards, ensure code quality, and mentor junior engineers. | 4+ years shipping production software with deep proficiency in Python, TypeScript, and SQL, proven feature ownership in fast-paced environments, and solving ambiguous problems. | ABOUT OUTMARKET Outmarket is the AI platform for insurance, trusted by more than 250 brokerages to run the work their business depends on. Commercial insurance still runs on dense documents and slow, manual workflows, and that is exactly what we automate: quote comparisons, coverage gap and tower analysis, policy review, and proposal generation, all grounded in our customers’ own data and source-cited so teams can trust the output. The impact is concrete. Teams save 12 to 15 hours per person every week, cut errors by roughly 65 percent, and win more business, all on infrastructure that is SOC 2 Type II certified, single-tenant, and never used to train AI models. We are an AI-first company in both what we build and how we work, shipping quickly and in close partnership with the agencies that rely on us. WHAT YOU’LL GET A high-impact role with ownership from day one. Competitive compensation and meaningful equity. Direct collaboration with founders and real users. Remote-first flexibility. The opportunity to help build an AI-native product from the ground up. ABOUT THE ROLE We are hiring a Senior Software Engineer to own meaningful parts of our AI-powered product end to end. You will lead the design and delivery of features and systems, set quality standards, and help less-senior engineers grow. WHY THIS ROLE Own systems and features that are core to the product. Shape technical direction and standards as the company scales. Partner closely with founders on high-leverage problems. WHAT YOU’LL DO Lead the design, build, and operation of features spanning AI, backend, and frontend. Make pragmatic architecture decisions and drive them to production. Raise the bar on code quality, testing, and reliability across the team. Mentor engineers and review work to keep velocity and quality high. WHAT WE’RE LOOKING FOR 4+ years building and shipping production software. Deep proficiency in Python and/or TypeScript, plus strong SQL and system design. Track record of owning features end to end in a fast-moving environment. Ability to turn ambiguous, messy problems into reliable, shipped systems. BONUS IF YOU HAVE Experience with LLM-integrated products, Postgres, ClickHouse, or React at depth. Early-stage startup experience.

Build AI-powered features and backend services to automate insurance workflows using modern AI technologies. | 1-3 years experience with Python, TypeScript, SQL, and strong understanding of AI systems including embeddings and model evaluation. | ABOUT OUTMARKET Outmarket is the AI platform for insurance, trusted by more than 250 brokerages to run the work their business depends on. Commercial insurance still runs on dense documents and slow, manual workflows, and that is exactly what we automate: quote comparisons, coverage gap and tower analysis, policy review, and proposal generation, all grounded in our customers’ own data and source-cited so teams can trust the output. The impact is concrete. Teams save 12 to 15 hours per person every week, cut errors by roughly 65 percent, and win more business, all on infrastructure that is SOC 2 Type II certified, single-tenant, and never used to train AI models. We are an AI-first company in both what we build and how we work, shipping quickly and in close partnership with the agencies that rely on us. WHAT YOU’LL GET A high-impact role with ownership from day one. Competitive compensation and meaningful equity. Direct collaboration with founders and real users. Remote-first flexibility. The opportunity to help build an AI-native product from the ground up. ABOUT THE ROLE We are hiring a Software Engineer to build AI-powered features across our product and technical stack. You will work on real customer workflows, from AI and backend systems to product experiences, with strong support from a senior team. WHY THIS ROLE Build features that directly affect real customer workflows and outcomes. Work across a broad technical stack in an AI-native environment. Grow quickly with mentorship from founders and experienced engineers. WHAT YOU’LL DO Build product features powered by LLMs, including retrieval-augmented generation (RAG), embeddings and semantic search, prompt design, structured output, and tool-using agents. Work hands-on with the mechanics of AI systems: chunking and embedding documents, vector stores and retrieval, context construction, and evaluating output quality. Build the backend services, data pipelines, and product UI that turn these AI capabilities into reliable, production-grade features. Turn messy real-world insurance data into trustworthy, source-cited product capabilities. Collaborate across product, sales, and customer success to ship high-leverage work. WHAT WE’RE LOOKING FOR 1 to 3 years of software engineering experience (or equivalent), with strong fundamentals. Proficiency in Python and/or TypeScript and comfort with SQL. A real understanding of how modern AI systems work under the hood: LLMs and prompting, tokens and context windows, embeddings and vector search, RAG, and basic evaluation of model output. Genuine interest in applied AI and a desire to go deep on the domain. Strong ownership and comfort in a fast-moving environment. BONUS IF YOU HAVE Hands-on experience with LLM orchestration and RAG tooling (for example LangChain, LlamaIndex, or similar) and vector databases (for example pgvector, Pinecone, or Weaviate). Experience building agents, tool/function calling, or evaluation and prompt-testing pipelines. Experience with React, Postgres, or cloud platforms, or with document-heavy data.

Own end-to-end data platform architecture including ingestion, transformation, and serving layers. | 5+ years data engineering experience with SQL, Python, and orchestration tools like Airflow or Temporal. | ABOUT OUTMARKET Outmarket is the AI platform for insurance, trusted by more than 250 brokerages to run the work their business depends on. Commercial insurance still runs on dense documents and slow, manual workflows, and that is exactly what we automate: quote comparisons, coverage gap and tower analysis, policy review, and proposal generation, all grounded in our customers’ own data and source-cited so teams can trust the output. The impact is concrete. Teams save 12 to 15 hours per person every week, cut errors by roughly 65 percent, and win more business, all on infrastructure that is SOC 2 Type II certified, single-tenant, and never used to train AI models. We are an AI-first company in both what we build and how we work, shipping quickly and in close partnership with the agencies that rely on us. WHAT YOU’LL GET A high-impact role with ownership from day one. Competitive compensation and meaningful equity. Direct collaboration with founders and real users. Remote-first flexibility. The opportunity to help build an AI-native product from the ground up. ABOUT THE ROLE We are hiring a Senior Data Engineer to own the architecture of our data platform end to end, spanning ingestion, transformation, and the analytical serving layer that powers insights and AI across every customer. You will set the standards for how we model and operate data at scale. WHY THIS ROLE Own the architecture of the data plane the whole product depends on. Solve hard, high-value problems with messy multi-tenant insurance data. Set data engineering standards and mentor the team. WHAT YOU’LL DO Architect ingestion and transformation pipelines (bronze → silver → fact) across many customers. Own multi-tenant data modeling and performance/cost across Postgres and ClickHouse. Define the standards for dataset configuration, KPIs, and reconciliation that keep data trustworthy. Build reliable, observable orchestration and lead data quality strategy. Mentor data and product engineers and review high-impact data work. WHAT WE’RE LOOKING FOR 5+ years in data engineering, including pipeline and analytical-data architecture. Deep SQL and Python, strong Postgres, and hands-on columnar-store experience (ClickHouse or similar). Experience with orchestration (Temporal, Airflow, Dagster) and large-scale data operability. Track record of setting standards and leading data work in a fast-moving environment. BONUS IF YOU HAVE Multi-tenant SaaS data experience. Insurance, fintech, or other regulated/document-heavy domain experience.

Lead architecture of complex AI, data, backend, and frontend systems while mentoring engineers and setting standards. | 7+ years experience with deep system design expertise and hands-on coding ability leading complex cross-team systems. | ABOUT OUTMARKET Outmarket is the AI platform for insurance, trusted by more than 250 brokerages to run the work their business depends on. Commercial insurance still runs on dense documents and slow, manual workflows, and that is exactly what we automate: quote comparisons, coverage gap and tower analysis, policy review, and proposal generation, all grounded in our customers’ own data and source-cited so teams can trust the output. The impact is concrete. Teams save 12 to 15 hours per person every week, cut errors by roughly 65 percent, and win more business, all on infrastructure that is SOC 2 Type II certified, single-tenant, and never used to train AI models. We are an AI-first company in both what we build and how we work, shipping quickly and in close partnership with the agencies that rely on us. WHAT YOU’LL GET A high-impact role with ownership from day one. Competitive compensation and meaningful equity. Direct collaboration with founders and real users. Remote-first flexibility. The opportunity to help build an AI-native product from the ground up. ABOUT THE ROLE We are hiring a Staff Software Engineer to provide technical leadership across teams without stepping out of the code. You will drive architecture for our most important systems, de-risk hard problems, and multiply the output of the engineers around you. WHY THIS ROLE Set the technical direction for systems that the whole product depends on. Solve the hardest cross-cutting problems in an AI-native platform. Influence how the entire engineering org builds, without managing people. WHAT YOU’LL DO Lead architecture for major systems spanning AI, data, backend, and frontend. Identify and remove the biggest technical risks and bottlenecks. Set engineering standards (design, testing, reliability, performance) and make them stick. Mentor senior engineers and raise the technical bar across teams. WHAT WE’RE LOOKING FOR 7+ years of software engineering, with a record of leading complex, cross-team systems. Deep system design expertise and strong hands-on coding ability. Demonstrated technical influence beyond your own direct work. Sound judgment about trade-offs, scope, and what to build vs. defer. BONUS IF YOU HAVE Experience scaling AI/ML systems or large data platforms. Early-stage startup or 0→1 product experience.