Top Tech Jobs & Startup Jobs in Chicago, IL

Build and operate full-stack, production-ready systems: design and ship AI-native mortgage automation, integrate third-party lending APIs, and architect scalable AWS infrastructure and job processing. Mentor engineers and ensure security, observability, and high reliability.

Drive new business sales by building consultative partnerships with brokers, agents, and distributors for voluntary benefits. Prospect, manage pipeline, deliver presentations, influence RFPs, and expand accounts. Coordinate with internal teams (implementation, underwriting, marketing), use Salesforce for reporting and forecasting, monitor competitive landscape, and contribute to sales planning and product development.

Manage and complete multi-week integration projects, troubleshoot data issues, and provide strategic guidance on implementation and project progress.

Design, build, and maintain scalable web applications using Python and React. Collaborate with teams and ensure application security and performance.

Design, build and maintain scalable, auditable analytics-ready data models (primarily in dbt) for PBM and care navigation. Implement data quality checks, CI/CD, documentation, pipeline orchestration, and partner with stakeholders to enable self-service analytics and AI-enabled workflows.

The role requires a skilled Machine Learning Engineer to create complex models and AI solutions while collaborating with teams to enhance products and services.

Lead US sales for an MSP, developing and executing go-to-market strategies, owning full sales cycles, acquiring enterprise and mid-market clients, building pipeline through prospecting and partnerships, representing the company at events, managing forecasts and CRM, and driving account growth and revenue targets.

The Head of Sales will build and lead a sales team, design revenue strategies, and manage pipeline performance. Responsibilities include coaching reps, establishing metrics, and reporting to the CEO. The role focuses on creating a high-performing sales organization at a startup stage with a strong emphasis on team leadership and strategic planning.

Manage the compliance risk program for mortgage lending by developing policies, ensuring adherence to laws, and conducting risk assessments.

The Senior Sales Engineer supports the sales team by designing solutions, articulating their value, and guiding decision-making through technical expertise and effective communication. Responsibilities include engaging in complex sales opportunities, collaborating with internal teams, managing pre-sales activities, and delivering client-focused presentations.