Outmarket AI

Role Description 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. Qualifications - 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. Requirements - 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. - 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. Benefits - 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. Company Description 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.

Role Description 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. Qualifications - 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. Requirements - 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. Benefits - 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.

Role Description We are hiring a Strategic Finance Manager to serve as a core operating partner to the Head of Finance & Strategy and the broader leadership team. This is a high-impact generalist role for someone who can turn ambiguous questions into structured analysis, sound decisions, and effective execution. - You will work across finance, operations, go-to-market, and technology. - One week you may be building a financial model for a board meeting. - The next, you may be standing up a pricing framework or driving a critical cross-functional initiative from idea to implementation. - If you need narrowly defined lanes, this role will be frustrating. - If you like building where there is no clear owner yet, you will likely thrive. Qualifications - 4 to 8+ years of experience in finance (investment banking, private equity), CDD consulting, and/or StratFin experience at a high-growth startup. - Strong analytical skills, including comfort with financial data, modeling, and spreadsheet-based analysis. - Structured thinking and the ability to break down ambiguous problems into practical next steps. - Strong execution skills and a willingness to own outcomes end to end. - Ability to build trust quickly with internal stakeholders and work effectively across functions. - Strong written and verbal communication skills. - Comfort moving between strategy, analysis, and hands-on execution without getting hung up on org boundaries. Requirements - Experience operating at a high-growth startup. - Experience building and maintaining a corporate financial model. - Experience supporting executive planning, investor materials, or board preparation in a high-growth environment. - Exposure to vertical SaaS, insurtech, or B2B operating models. Benefits - Direct partnership with the founding team at a company defining a new category in commercial insurance. - The opportunity to build AI-first functions and operating systems from the ground up. - A front-row seat to hyper-growth in the AI era, with real autonomy and scope. - Competitive compensation, meaningful equity, and clear room to grow. - Remote-first flexibility.

Role Description 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. Qualifications - 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. Benefits - 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.

Role Description 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. 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. Qualifications - 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. Benefits - 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.

Role Description We are hiring a Data Engineer to own the data plane that powers our analytics and AI products, from ingesting messy, real-world insurance data to the transformation pipelines and serving layer our customers rely on. You will turn fragmented source-system data into clean, trustworthy datasets that drive insights and automation. What You'll Do - Build and operate ingestion pipelines from agency management systems, carriers, and documents. - Design transformation layers (bronze → silver → fact) and the models that serve insights and dashboards. - Model and tune data across Postgres and ClickHouse for correctness, performance, and cost. - Define dataset configurations, KPIs, and reconciliation checks that keep numbers trustworthy. - Orchestrate reliable, observable data jobs and own data quality end to end. Qualifications - 2+ years building production data pipelines with strong SQL and Python. - Solid relational modeling experience (Postgres) and comfort with large analytical datasets. - A track record of turning messy, inconsistent source data into reliable product capabilities. - Strong ownership and comfort operating in a fast-moving environment. Bonus If You Have - Experience with ClickHouse or another columnar/analytical store. - Experience with workflow orchestration (e.g., Temporal, Airflow, Dagster). - Exposure to insurance, fintech, or other document- and data-heavy domains. Benefits - 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.

Role Description We are hiring an IT Engineer to own our internal systems and corporate IT: identity, devices, SaaS, and the automation that keeps the company running smoothly and securely as we scale. Qualifications - 3+ years in IT engineering / systems administration / IT operations. - Hands-on with identity/SSO (Okta or similar), Google Workspace, and MDM/endpoint tooling. - Scripting/automation ability (e.g., Python, Bash) and a security-conscious mindset. - Strong service orientation and clear communication. Requirements - Own identity and SSO (e.g., Okta) and provisioning into downstream tools (Google Workspace, Slack). - Manage device lifecycle and endpoint security (MDM), and harden internal systems. - Administer SaaS applications, access, and licensing; run onboarding and offboarding. - Automate internal IT workflows and provide responsive support to the team. - Maintain internal networking and contribute to security and compliance posture. Benefits - 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.

Role Description We are hiring a Platform Engineer to own the runtime our entire product sits on: infrastructure, orchestration, CI/CD, observability, and developer experience. You keep an AI-native, multi-tenant platform reliable, fast, and easy to build on. Qualifications - 4+ years in platform/infrastructure/DevOps/SRE with production ownership. - Strong Kubernetes, Terraform, and a major cloud (GCP/AWS). - Solid CI/CD and observability experience, plus scripting in Python or Go. - A reliability mindset and calm under incidents. Requirements - Own Kubernetes (GKE), infrastructure-as-code (Terraform), and our cloud (GCP) footprint. - Build and operate CI/CD, observability (logs, metrics, traces), and orchestration (Temporal, gateway/Kong). - Improve reliability, performance, and cost across services and the data plane’s infrastructure. - Strengthen multi-tenant provisioning reliability and internal developer experience. - Lead on-call practices and incident response. Benefits - Own the foundation the whole product and team depend on. - Shape reliability, performance, and cost for a multi-tenant AI platform. - Multiply every engineer’s output through better tooling and infrastructure. Bonus If You Have - Multi-tenant SaaS or data-platform infrastructure experience. - Temporal, Kong/API gateway, or ClickHouse operations experience.

Role Description 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 - 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 - 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. Qualifications - 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

Role Description We are hiring a Security Engineer to own product and application security for a multi-tenant platform handling sensitive insurance data. You will build security into how we ship, across secure SDLC, AppSec, cloud posture, and supply-chain, and lead our response when issues arise. Qualifications - 4+ years in security engineering, with strong application security depth. - Hands-on experience securing cloud-native, multi-tenant systems. - Working knowledge of OWASP-class risks and how to prevent them in real code. - Ability to partner with engineers and make security practical, not blocking. Requirements - Drive secure SDLC and security-focused code review across the engineering org. - Own application security: authz, tenant isolation, SSRF and injection prevention, secrets management. - Strengthen cloud security posture (GCP IAM, egress controls) and supply-chain controls. - Coordinate penetration testing, threat modeling, and vulnerability management. - Lead incident response and advance compliance readiness (e.g., SOC 2). Benefits - 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.