Top Tech Jobs & Startup Jobs in Chicago, IL

Lead technical pre-sales engagements for insurance carriers and MGUs, including discovery, solution design, demos, RFPs, security questionnaires, and platform configuration. Translate insurance workflows into quoting, rating, endorsement, and portfolio optimization solutions. Build reusable demo environments, onboarding materials, configuration libraries, and pre-sales playbooks while collaborating with Sales, Product, Engineering, Security, Marketing, Implementation, and Customer Success. Support roadmap alignment and communicate technical value to executive and practitioner audiences.

Generate qualified pipeline for named insurance accounts through phone, email, and social outreach. Business Development Representatives partner with Sales Directors and ABM teams to map accounts, identify decision-makers, tailor prospecting to carriers and MGAs, and coordinate outreach. The role also requires learning insurance underwriting and explaining AI-native policy administration workflows. Success depends on thoughtful prospecting, strong writing, phone confidence, initiative, resilience, and consistent account planning.

Lead and grow an engineering team building scalable AI-native insurance products. Responsibilities include hiring, mentoring, performance management, technical direction, architecture guidance, design reviews, and delivery of reliable production systems. Partner with Product, Design, Data Science, and customer-facing teams to execute ambiguous initiatives. Use AI-native development workflows to increase velocity while maintaining high standards for security, correctness, reliability, and production readiness.

Build backend architecture and infrastructure for LLM-driven agent systems, including orchestration, tool integration, context management, evaluation, observability, and production deployment. Develop services connecting AI models with insurance data and platform APIs, define reliable AI-native architectural patterns, and collaborate with product, design, and engineering teams to deliver underwriting workflows.

Lead and scale Federato’s U.S. sales organization by building and coaching a high-performing team, driving strategic and complex SaaS deals, developing customer relationships, partnering with Marketing, Product, and Customer Success, and reporting sales insights to executives and the board. Establish a performance-driven culture while exceeding revenue goals and improving pipeline and forecasting discipline.

Own the full enterprise sales cycle for complex insurance software deals, from prospecting through closure. Develop account-based strategies, acquire new logos, build executive relationships, conduct value-based discovery, position AI solutions, and consistently exceed quota. Partner with marketing, SDRs, solutions engineering, legal, customer success, product, and delivery teams to advance opportunities and execute sales strategy.

Design, develop, modify, test, and maintain full-stack software applications. Engineers will understand product areas, codebases, and systems; write high-quality, tested code; analyze data; solve complex problems; collaborate with product and engineering teams; conduct design and code reviews; and mentor junior developers while delivering customer-focused products.

Lead a small engineering team to design, build, and deliver full-stack features using React, TypeScript, Python (Django), Node.js, and PostgreSQL. Own technical delivery from design through deployment, driving testing, CI/CD, containerized deployments (Kubernetes), event-driven architectures (Kafka), performance, reliability, and mentoring across the team while partnering with Product and Design.