Top Tech Jobs & Startup Jobs in Chicago, IL

Leads major technical initiatives while designing enterprise identity systems, authorization models, and scalable multi-tenant SaaS architecture. Builds platform components with .NET/C# on AWS, improves data pipelines, resolves complex production issues, and shapes the technical roadmap. Mentors engineers, drives architecture and reviews, coordinates across teams, and supports security, compliance, automation, and continuous platform improvement.

Leads the strategy, content roadmap, and certification programs for AbsenceSoft University. Manages a growing team while remaining hands-on with course and exam development, LMS administration, reporting, and platform integrations. Partners with Product, Compliance, Legal, and industry organizations to maintain accurate, current training on leave and accommodations. Oversees program performance, customer enablement, credential renewals, and compliance-sensitive content.

Lead the vision, strategy, roadmap, and execution of a compliance platform encoding more than 200 statutory leave and accommodation laws. Manage product managers and compliance experts, translate regulations into scalable features, maintain content accuracy, and apply AI and automation responsibly. Partner with Legal, Engineering, Design, Sales, and Customer Experience to deliver compliant products, support go-to-market readiness, measure outcomes, represent customer needs, and identify regulatory risks and opportunities.