Top Tech Jobs & Startup Jobs in Chicago, IL

Leads technology and executive recruiting strategies, sourcing, assessment, and hiring initiatives. Partners with technology executives, hiring managers, HR leaders, and candidates to build talent pipelines, deliver strong candidate experiences, and ensure compliant recruiting practices. Analyzes labor-market and recruitment data, manages vendors and service levels, leads recruiting projects, advises on talent trends, and mentors other talent acquisition consultants.

Supports Technology Innovation Office initiatives by helping business teams identify opportunities, align stakeholders, adopt AI and automation capabilities, and realize measurable value. Coordinates innovation engagements, workshops, intake and prioritization, stakeholder requirements, communications, training, reporting, dashboards, impact analysis, and governance alignment. The role requires consulting, business analysis, transformation, or project delivery experience, along with strong facilitation, analytical, organizational, and communication skills.

Leads innovation engagements supporting an AI and automation roadmap. Responsibilities include discovering and prioritizing opportunities, developing business cases, facilitating cross-functional delivery, tracking value and adoption, managing risks, enabling organizational change, communicating with executives, and mentoring consultants. The role requires applying emerging technologies in regulated environments and driving initiatives from discovery through implementation.

Leads AI engineering strategy, team development, and delivery of scalable AI and machine learning solutions. Provides technical guidance on solution design, MLOps, automation, DevSecOps, testing, and operational readiness. Partners with business, data, security, architecture, and technology stakeholders to translate requirements into secure, reliable capabilities. Oversees delivery risks, dependencies, quality, governance, responsible AI practices, and continuous improvement while communicating progress and outcomes to leadership.

Leads the development, configuration, maintenance, testing, support, and optimization of Workday HRIS capabilities across multiple functional areas. Partners with HR, business units, IT, and senior leaders on requirements, security, reporting, integrations, software updates, process improvements, governance, and enterprise projects. Provides end-user support, creates job aids, advises on system enhancements, develops strategic roadmaps, and mentors less experienced team members.

Manages state tax compliance, research, planning strategies, and tax accounting processes. Reviews GAAP and statutory tax elements, leads tax projects and process improvements, oversees external consultants and vendors, identifies control weaknesses, and coordinates tax integration efforts. The role interacts with the IRS, auditors, regulators, and senior tax leadership while translating complex tax information into actionable guidance.

Perform independent actuarial analysis supporting Pension Risk Transfer pricing. Responsibilities include coding and executing proprietary pricing models, recalculating premiums, maintaining and improving processes, calculating complex participant benefits, reviewing standard calculations, drafting contract language, and supporting special projects. The role requires collaboration, technical communication, attention to detail, and continued actuarial accreditation.

Performs complex tax research, data analysis, tax planning, and tax accounting review. Manages tax processes, projects, controls, external consulting resources, and tax integrations. Interacts with the IRS, auditors, regulators, vendors, and senior tax leadership while translating technical tax information into actionable guidance.

Lead analysis, design, development, testing, debugging and production support for complex insurance application systems (OIPA/PAS). Mentor team members, resolve outages, implement SDLC practices, and support data migration and monitoring for a multi-year OIPA implementation.

The Lending Compliance Counsel supports designing and delivering compliant financial products, ensuring they meet regulatory standards and market needs, while educating stakeholders about industry trends.