Top Tech Jobs & Startup Jobs in Chicago, IL

Lead and mature Plenful’s company-wide security program across application, cloud, infrastructure, security operations, incident response, compliance, and customer trust. Manage a small team, establish security roadmaps and controls, partner with engineers on vulnerability remediation and secure development, strengthen AWS and AI/ML security, oversee SOC 2, HIPAA, and HITRUST initiatives, and communicate security risks to executives, customers, auditors, and cross-functional stakeholders.

Set technical direction for production AI agents, LLM and vision-language model post-training, evaluation, MLOps, and data improvement systems. Architect agent orchestration, retrieval, observability, and failure recovery; establish quality and release standards; and ship measurable model improvements. This hands-on individual contributor will co-own the ML roadmap, lead technical reviews, mentor engineers, support hiring, and implement privacy-conscious, HIPAA-aware practices.

Build and operate Python and FastAPI platform services powering healthcare workflows, while developing end-to-end frontend features with JavaScript, TypeScript, and React. Responsibilities include API design, data modeling, system integrations, reliability, observability, performance improvements, code reviews, mentoring, and project ownership from design through launch. The role partners with product, design, and engineering teams to deliver secure, maintainable, accessible solutions.

Lead the architecture and evolution of Plenful’s frontend UX platform, including shared components, design system foundations, developer tooling, and reusable infrastructure. Build user experiences with TypeScript and React, integrate APIs using Python and FastAPI, and establish standards for accessibility, performance, testing, and maintainability. Collaborate with design, product, and engineering teams, mentor engineers, review technical designs, and drive frontend improvements across multiple teams.

Design, build, and deploy production-grade ML models and scalable pipelines (training, inference, monitoring) using NLP/LLM, classification, recommendation, and prediction techniques. Collaborate with product and engineering, optimize latency and costs, and implement retraining and observability for healthcare workflow automation.

Design, build, and maintain cloud infrastructure, IaC, and CI/CD for serverless and containerized services. Improve developer experience with internal tooling and self-serve abstractions. Define observability standards, investigate performance bottlenecks, support incident response, and automate security and compliance workflows. Participate in on-call rotation and postmortems to improve reliability and operational excellence.

Build and scale cloud infrastructure, IaC, and CI/CD; standardize deployments across serverless and containers; improve developer experience and self-service tooling; define observability and reliability practices; automate security/compliance workflows; participate in on-call incident response and postmortems.

Build and ship end-to-end full‑stack features for pharmacy and health system workflows. Partner with product and operations, own design through production and support, embed AI into workflows, review code, and contribute to platform durability and scaling in a compliance‑critical healthcare environment.

Own production reliability and performance for a healthcare AI platform: define SLIs/SLOs, run incident response and postmortems, build observability and automation, optimize scalability across serverless and container services, and partner with engineering, security, and compliance to improve operational maturity.

Drive quality strategy across multiple products by designing, building, and maintaining automated test suites for web apps, APIs, and backend services. Integrate tests into CI/CD, define test plans and acceptance criteria, perform exploratory and regression testing, monitor production quality metrics, and mentor engineers on testing best practices.