Top Tech Jobs & Startup Jobs in Chicago, IL

Build and ship AI-powered automation features, third-party integrations, full-stack web applications, and cloud infrastructure. Design background job processing systems, improve reliability and observability, address security risks, contribute product ideas, and mentor junior engineers. The role requires strong TypeScript skills, experience scaling AWS systems with infrastructure as code, and proficiency with React, Node.js, and Postgres.

Handle a full docket of employer and insurer defense matters from fact-finding through trial. Conduct depositions, hearings, and case strategy; develop client relationships and new business; meet monthly billing targets; and coach junior attorneys. The role requires at least five years of relevant defense experience, a JD, California Bar admission or eligibility, substantial litigation experience, independence, and a long-term commitment to the practice area.

Own end-to-end product design for a core SaaS product area, including discovery, usability research, interaction design, high-fidelity Figma work, design systems, and delivery. Design complex financial workflows, automation experiences, AI interfaces, dense tables, and decision screens. Collaborate closely with customers, Product, Engineering, and code-based prototyping efforts. The role requires strong B2B workflow experience, a high-quality portfolio, advanced Figma skills, and domestic client travel.

Handle a transactional legal caseload by drafting and negotiating agreements, policies, opinion letters, corporate documents, and governance materials. Advise clients on governance, statutory compliance, property restrictions, real estate, and voting procedures. Manage client communications, meet billing targets, contribute published articles, and support educational and marketing activities while working remotely with minimal supervision.

Leads a technology and intellectual property transactions practice, negotiating complex commercial agreements and overseeing IP diligence for investments, acquisitions, divestitures, and spin-offs. Advises senior client stakeholders, develops transaction methodologies, recruits and mentors attorneys, and collaborates with engineers on legal automation and tooling. Requires extensive technology transactions experience, active bar membership, law firm and in-house backgrounds, and expertise in software licensing, cloud terms, data and AI provisions, open source, trade secrets, and IP representations.

Independently manage a full civil litigation docket from pleadings through trial, including property, insolvency, and post-judgment matters. Handle pleadings, motions, discovery, hearings, client communications, and court appearances while meeting an annual 1,800 billable-hour target. Work with managing partners to develop specialized legal expertise and maintain exceptionally high-quality written advocacy.

Lead a demand generation team responsible for marketing-sourced pipeline through account-based marketing, paid media, events, webinars, and customer expansion programs. Manage budgets, target-account strategy, funnel forecasting, conversion testing, agencies, and three direct reports. Partner closely with sales, report results to senior leadership, and use AI tools for research, personalization, content, and campaign analysis. The role requires extensive B2B demand generation experience, US-market expertise, people leadership, and familiarity with long sales cycles.

Own the full-stack design and development of a customer-facing web application in partnership with company founders. Build features using TypeScript and Python, create polished interfaces, and take products from customer discovery through release. Develop demos, launch materials, and promotional campaigns while using analytics and customer feedback to prioritize work. The role requires LLM and agent-based systems experience, strong product judgment, and the ability to work independently in a remote startup environment.

Lead go-to-market and growth for technical software products, including positioning, launches, content, developer-community engagement, funnel analytics, onboarding, retention, and revenue growth. Build acquisition systems, run experiments, create demos and customer stories, and help establish the company’s initial growth team. The role requires close collaboration with founders, engineers, researchers, and product teams in a remote US environment.

Build and productionize machine learning systems that convert complex documents into executable, verifiable logic. Responsibilities include developing parsing and transformation pipelines, experimenting with language models, designing datasets and evaluation metrics, creating adversarial tests, analyzing model failures, and implementing rule-based checks using logical reasoning and program analysis. The role requires close collaboration with founders and subject-matter experts to validate system outputs.