Top Tech Jobs & Startup Jobs in Chicago, IL

Support pricing strategies and rating model development for individual and small-employer commercial markets. Build and maintain actuarial models, analyze and forecast risk/data, coordinate special pricing projects, and prepare regulatory rate filings with internal teams and state/federal agencies.

Write, edit, and advise on marketing and sales communications (proposals, presentations, retention materials) for presale and acquisition/retention. Partner with business and creative teams, ensure legal and brand compliance, assess communication effectiveness, and recommend efficiency and clarity improvements.

Lead and execute enterprise strategy projects: identify and prioritize initiatives, manage cross‑functional programs, perform advanced analyses, present recommendations to senior leadership, facilitate large working sessions, and coach teams on continuous improvement and metrics reporting.

Senior HR strategic advisor partnering with C-suite to shape workforce strategy, organizational design, leadership capability, and culture. Leads enterprise workforce planning, predictive analytics, large-scale change initiatives, cross-functional HR alignment, executive coaching, and measurement of talent program ROI to drive organizational performance and resilience.

Lead architecture, development, and deployment of large-scale AI systems and platforms. Define enterprise AI standards, modernize legacy systems, implement AI-enabled SDLC and governance, mentor engineers, and drive adoption of LLMs, agentic AI, microservices, cloud, and DevOps practices.

Lead and coach Agile teams to ensure delivery predictability and remove impediments. Facilitate Scrum/Kanban ceremonies, manage stakeholder communications, track dependencies, support release coordination across distributed teams, and drive continuous improvement for medium-to-large technical systems.

Serve as an internal HR consultant solving complex workforce challenges via sprint-based projects. Lead org design, workforce analytics, talent optimization, change enablement, and agile sprint execution. Mentor junior staff, create scalable solutions and playbooks, diagnose problems through stakeholder interviews and data, and co-create evidence-based HR solutions with business partners.

Perform actuarial and statistical analyses to support commercial rate determination, update pricing and forecasting models, validate and prepare data, assist with regulatory filings, mentor analysts, and contribute to new product pricing and special projects.

Lead international tax compliance and planning, manage Forms 5471/8858, calculate GILTI/Subpart F/FDII, support ASC 740 tax provision, handle international audits, perform tax due diligence, mentor junior staff, and partner on tax technology and process improvements.

Lead design and execution of AI compliance monitoring, audits, and control assessments. Develop risk-based monitoring plans, implement automated monitoring, synthesize findings into reports, advise on controls and remediation, and build training and oversight frameworks.