Top Tech Jobs & Startup Jobs in Chicago, IL

Lead the Total Rewards Center of Excellence and define strategy across compensation, benefits, wellbeing, and recognition. Oversee governance, compliance, vendor management, pay frameworks, annual compensation cycles, executive compensation, benchmarking, and team development. Partner with HR and business leaders to align programs to business goals and ensure regulatory and audit readiness.

Design, build, and maintain automation and IaC for Azure and Microsoft 365 environments. Automate identity, licensing, Teams/Exchange/SharePoint workflows using Microsoft Graph API and PowerShell. Implement and operate Azure services, Entra ID, Windows Server, and ensure security, compliance, and disaster recovery. Collaborate with cross-functional teams to reduce manual effort and improve reliability.

Lead and manage underwriting support operations for Management Liability: supervise account managers and supervisors, ensure policy issuance and renewals, enforce quality/compliance, drive process improvements and automation, partner with underwriting and technology, manage staffing, budgets and stakeholder communications.

Lead full-cycle recruiting for niche P&C insurance roles; proactively source passive candidates using advanced tools, build diverse pipelines, partner with hiring managers, present hiring metrics, and champion inclusive hiring while managing candidate communications and training as needed.

Partner with senior leaders to drive people strategy, org design, workforce planning, talent and succession, and change leadership. Provide counsel on employee relations, performance management, and organizational health; use data to guide decisions; simplify HR processes and partner with HR Operations/COEs to enable strategic outcomes and improve leader capability and talent retention.

Manage national Management Liability claims (EPL, D&O, Fiduciary, Crime) including investigation, coverage analysis, defense counsel management, litigation strategy, reserving, reporting, and stakeholder communication. Support underwriting and recovery efforts while maintaining required adjuster licensure.

Lead design and execution of enterprise talent strategies—talent reviews, succession planning, leadership and high-potential development, career pathways, talent analytics, and change management—partnering with HRBPs, leaders, and HR Technology to drive adoption and measure impact.

Handle management liability claims (EPL, D&O, fiduciary, crime) for private and nonprofit clients: investigate, analyze coverage, set reserves, manage defense counsel, negotiate resolutions, attend mediations/trials, prepare loss reports, pursue recoveries, and support underwriting and business partners. Maintain required adjuster licenses and comply with policies and regulatory standards.

Manage the companys most complex commercial liability claims (construction defect, general liability, auto/trucking) with high financial exposure. Oversee investigations, experts, defense counsel, litigation strategy, reserves, subrogation, and stakeholder communications. Ensure coverage analysis, settlement negotiations, and compliance with reporting and licensing requirements.

Handle management liability claims (EPL, D&O, fiduciary, crime) for private and non-profit clients: investigate, analyze coverage, set reserves, manage defense counsel, develop litigation strategy, attend mediations/trials, prepare reports, pursue recoveries, maintain adjuster licensing, and support underwriting and business partners.