Top Tech Jobs & Startup Jobs in Chicago, IL

Provides technical leadership across multiple agile engineering teams, designing, developing, and maintaining complex distributed software systems. Responsibilities include translating product requirements into scalable designs, writing and reviewing code, leading sprint teams, removing delivery impediments, mentoring engineers, collaborating with product managers, and guiding technical strategy. The role emphasizes microservices, cloud platforms, containerization, APIs, messaging, workflow orchestration, DevSecOps, observability, performance, security, and operational excellence.

Serves as a strategic compensation partner to business groups, advising leaders on pay decisions, job evaluations, market benchmarking, annual compensation cycles, incentive programs, and equity recommendations. The role improves compensation processes, tools, governance, and HRIS workflows; ensures regulatory compliance; performs financial modeling and analysis; develops manager guidance; and coaches junior compensation professionals.

The Senior Project Manager leads multiple development, infrastructure, and software acquisition projects from concept through implementation. Responsibilities include creating project charters, plans, estimates, and status reports; coordinating cross-functional teams and vendors; tracking deliverables, risks, issues, and changes; ensuring quality standards; resolving problems; and communicating progress to business sponsors. The role also provides project management guidance to technical teams and manages expectations, resources, negotiations, and team performance.

Leads test engineering strategy for complex software projects, designing comprehensive test plans, executing manual and automated testing, and improving automation coverage. Develops test scripts, manages defects, analyzes quality metrics, integrates testing into CI/CD pipelines, and drives process improvements. Collaborates with engineering, product, and business teams while reviewing test strategies and cases. Mentors test engineers and establishes testing policies, standards, and best practices across multiple teams.

Respond to customer interactions across phone, chat, SMS, email, and social media. Support policy and billing questions, process transactions and policy changes, resolve payment and account issues, investigate system defects, document interactions accurately, protect customer privacy, and handle escalated concerns while meeting service and performance standards.

Leads People Operations process discovery, inventory, redesign, and implementation. Builds process maps, future-state workflows, governance, documentation, roadmaps, and measurement frameworks. Coordinates cross-functional operational programs, including HRIS replacement, service-model improvements, automation, and readiness initiatives. Drives pilots through adoption with communications, training, feedback, and continuous improvement. Establishes PMO practices, tracks risks and outcomes, and ensures processes are measurable, sustainable, and easier for employees and leaders to navigate.

Build and maintain people-data pipelines, analytical datasets, metric definitions, dashboards, and self-service data products. Conduct statistical analysis, forecasting, experimentation, segmentation, and predictive modeling to address workforce questions such as attrition, capacity, performance, and productivity. Translate findings into actionable recommendations for leaders while establishing standards for data quality, privacy, documentation, governance, and responsible AI use. Partner across People, Finance, HR Tech, and data teams to shape the analytics roadmap and improve adoption of trusted workforce insights.

Performs advanced accounting functions, including subsidiary general ledger analysis, complex financial reporting, and preparation of monthly, quarterly, and annual financial statements under GAAP and statutory accounting principles. Conducts financial analyses and special projects, supports footnote disclosures, and may coordinate with external auditors. Requires a bachelor’s degree in accounting and at least five years of accounting experience, including two years in public accounting.

Leads product strategy, research, development, pricing, and implementation for homeowners and landlord insurance products. Oversees research plans, statistical analysis, competitor and market insights, product governance, portfolio prioritization, training, and performance monitoring. Manages and develops R&D teams while coordinating with actuarial, underwriting, sales, claims, and other stakeholders to implement product enhancements, improve processes, and support profitable growth.

Leads and manages software engineering teams, including hiring, mentoring, budgeting, planning, roadmap delivery, system design, and technical strategy. Oversees scalable, secure, compliant applications across multiple technology stacks, drives CI/CD, migrations, modernization, process improvement, and engineering best practices, and partners with product and cross-functional stakeholders to deliver high-quality customer-facing solutions.