Top Tech Jobs & Startup Jobs in Chicago, IL

Design, develop, and maintain scalable Python applications and cloud-native solutions. Architect microservices, containerized deployments (Docker/Kubernetes), optimize cloud infrastructure, build CI/CD pipelines, integrate messaging systems, ensure security and high code quality, and mentor junior developers. Generative AI/ML experience is a plus.

Lead security assessments and controls across cloud-hosted applications, APIs, mobile (Flutter), CI/CD, and infrastructure. Implement and harden shared security tooling (dependency/secret/static/container scanning), review IAM and privileged access, support incident readiness and monitoring, evaluate SRE/recovery changes for security impact, and coordinate remediation with system owners. Establish security policies, automation, and review triggers to integrate practical controls into engineering workflows.

Sell Portside’s cloud-based aviation software solutions to business aviation, airline, and aircraft leasing clients. Responsibilities include prospecting, presenting and demonstrating SaaS products, managing client relationships, collaborating with marketing and product teams on sales strategies, monitoring industry trends, and achieving sales targets. The role is fully remote but requires travel up to 30% of the time.

Write and publish high-quality blog posts and case studies by researching eCommerce/logistics topics and interviewing customers. Propose original content ideas, craft narratives that showcase customer success and Wondys impact, collaborate with the team, use Figma/Framer/HubSpot/Google Workspace for content workflows, and track content performance to improve engagement.

Create short-form finance and Excel content that demonstrates TabAI workflows, engage and educate audiences across social platforms, experiment with formats and insights, collaborate with TabAI on prompts and creative direction, and drive subscriptions via affiliate links while building a personal brand.

Build and deploy production-grade LLM applications, AI agents, models, and scalable RAG pipelines for investment and business workflows. Architect secure MCP integrations with enterprise systems, establish MLOps and LLMOps practices, optimize model performance and latency, and develop evaluation, monitoring, governance, and rollback processes. Collaborate with data engineering and platform teams to provide secure, governed access to organizational data.

Provide remote administrative and legal support to law firms: manage schedules, coordinate meetings, draft documents, perform legal research, communicate with clients, and maintain organized workflows. Must adapt to legal software and digital tools, multitask, and uphold high attention to detail and professionalism.

Own and grow Investing.com's French affiliate and partnership ecosystem. Responsibilities include recruiting and managing influencers, content creators, media outlets, affiliate networks, and commercial partners; executing co-marketing campaigns; optimizing performance and subscription conversions; supporting social media growth; analyzing campaign data and competitors; and collaborating with marketing, product, and data teams.

Hands-on growth-focused engineering role: create content, manage community and partnerships, and build production-grade LLM-powered systems with client teams. Embed with clients, own technical architecture, ship reliable AI/ML applications (RAG, agents, fine-tuning), transfer knowledge, contribute to documentation and internal tooling, and support go-to-market and sales activities.

Support day-to-day people operations for a distributed US-based team: coordinate onboarding/offboarding, process payroll inputs, assist benefits enrollment, maintain HR records, serve as first contact for routine employee questions, support leave administration, coordinate vendor/EOR interactions, run employee programs and events, and cover expanded HR responsibilities during a planned leave (Dec–May). Identify process improvements and maintain operational playbooks.