Top Tech Jobs & Startup Jobs in Chicago, IL

Gathers and documents technical business requirements through research and stakeholder interviews. Translates product vision into functional and technical specifications, process flows, and business rules for development teams. Supports requirements validation, testing, web-based applications, system configurations, and internal technical services. Collaborates with end users and stakeholders to ensure solutions meet business needs.

Provisions and supports Azure cloud infrastructure, Terraform modules, and Azure DevOps CI/CD pipelines. Manages Azure resources, landing zones, networking, identity, security controls, monitoring, compliance, cost optimization, and deployment automation. Troubleshoots infrastructure and pipeline issues, supports incident response, and partners with application, security, networking, and operations teams. The role also develops runbooks, maintains environment parity, and delivers governed, reliable, production-ready DevOps capabilities.

Manages end-to-end onboarding and implementation for new and renewing employer group insurance clients. Configures rates, benefits, commissions, and eligibility rules; coordinates clients, producers, TPAs, technology partners, and internal teams; leads kickoff meetings and stakeholder reviews; troubleshoots implementation issues; supports testing, documentation, training, and post-launch support. The role also drives process improvements and provides subject matter expertise and mentorship within group insurance onboarding.

Own the digital measurement ecosystem across websites, quote engines, customer portals, and account applications. Lead Google Tag Manager tracking frameworks, data-layer standards, Google Analytics 4 configuration, conversion events, attribution, funnel analysis, experimentation measurement, data-quality audits, and analytics governance. Partner with Marketing, Product, Engineering, and Data teams to translate customer behavior into actionable insights that improve growth, conversion, and customer experience.

Lead and execute high-visibility brand and motion design across a portfolio of pet insurance brands. Create strategic visual concepts for digital, print, social, web, email, and paid channels. Mentor junior designers, partner with stakeholders, present creative rationale, and maintain brand consistency while managing multiple projects and timelines.

Lead accounting operations and a reporting team to improve AP, intercompany, investment, and banking workflows; drive reporting automation, controls, and UAT for system integrations; partner with FP&A, Procurement, IT, and external auditors; manage statutory and management reporting, reconciliations, accruals, and close processes while scaling processes and metrics across the organization.

The Product Analyst will analyze product performance, develop reports, and collaborate with stakeholders to enhance pet insurance offerings through data-driven insights.

The Director of Governance, Risk, and Compliance oversees the implementation of risk management and compliance programs across the enterprise. Responsibilities include regulatory compliance, audit leadership, third-party risk management, and collaboration across teams to ensure effective governance and oversight.

Lead underwriting strategy and governance for Doubtless North American carriers, set underwriting philosophy and risk appetite, oversee delegated authority and MGA oversight, ensure regulatory compliance, monitor portfolio performance, implement controls and audits, and partner cross-functionally to drive disciplined, profitable growth.