Top Tech Jobs & Startup Jobs in Chicago, IL

Create and rapidly test performance-driven video content for social gaming campaigns. Develop hooks, concepts, scripts, gameplay edits, creator footage, and AI-generated assets; analyze metrics such as hold rate, watch time, and click-through rate; iterate winning concepts across Meta, TikTok, Snapchat, YouTube, and other platforms; organize creative assets; and collaborate with User Acquisition and marketing teams to improve production workflows.

Leads the payments and banking product roadmap for a regulated cannabis fintech platform. Owns product vision, KPIs, market research, compliance requirements, partner integrations, prioritization, and customer adoption. Collaborates with executives, financial institutions, fintech providers, designers, engineers, marketing, and account teams to launch embedded payment, banking, liquidity, and credit capabilities.

Full-cycle enterprise sales role responsible for prospecting, developing, qualifying, and closing deals with large, multi-stakeholder organizations. The position sells FacilitiesLink, a facilities information platform for planning, building, and operating large-scale campus environments. Compensation includes 50% commission, a $20-per-hour guaranteed draw, and on-target earnings starting at $150,000 annually. Flexible work arrangements are available, with occasional travel required.

Leads and scales the implementation team, manages and mentors implementation specialists, optimizes deployment playbooks, oversees implementation risk and quality, handles executive escalations, and partners with Sales, Product, Engineering, and Client Success. Tracks implementation KPIs, resource utilization, backlogs, and CRM data integrity while driving faster customer time-to-value, retention, and account growth.

Owns executive relationships and revenue growth for 2–4 high-value enterprise accounts. Develops multi-year account plans, expands product adoption, identifies cross-sell and upsell opportunities, leads renewals and contract negotiations, and coordinates Product, Marketing, Client Success, and Solutions teams. The role also conducts strategic business reviews, represents the company with senior stakeholders, and drives profitable long-term partnerships across Roadside Assistance and Accident Management offerings.

Lead technical strategy and execution for multi-quarter initiatives, build and maintain software systems using AI, mentor and elevate engineers, collaborate across disciplines, and protect user privacy and security. The role involves working in an AWS and Kubernetes environment with technologies including Python, TypeScript, React, Go, Airflow, dbt, and Claude Code.

Build and ship production AI systems across retrieval, knowledge graphs, inference, agentic workflows, and data platforms. Develop customer-context retrieval, scored signals, evaluation and observability capabilities, and workflows that turn insights into action. Work hands-on with large and small models, durable orchestration, cloud deployment, inference-cost optimization, and high-volume observability data. Establish reusable engineering patterns, collaborate with product and platform teams, and mentor through strong technical contributions.

Administers and analyzes sales compensation programs, including commission payout processing, data auditing, dispute resolution, plan modeling, reporting, and dashboard maintenance. Partners with sales, finance, and HR teams to ensure accurate payouts, compliance, documentation, and process improvements. Requires strong Excel modeling skills, CRM and incentive compensation platform experience, analytical ability, communication skills, and independent judgment.

Design, build, and operate high-throughput, low-latency ad-serving infrastructure processing millions of requests per second. Optimize GPU-powered TensorRT inference, feature stores, model serving, benchmarking, experimentation tooling, and system reliability. Partner with machine learning engineers to productionize models and own systems through design, deployment, observability, capacity planning, incident response, and optimization.

Design and scale data pipelines and ML/LLM systems, build agentic automation for pipeline generation and maintenance, improve data monitoring, and collaborate with analysts, product, and ML teams to deliver reliable end-to-end data and AI infrastructure for a high-growth e-commerce platform.