Top Tech Jobs & Startup Jobs in Chicago, IL

Conduct client security risk assessments against NIST, ISO 27001, and CIS frameworks; evaluate controls and evidence, identify vulnerabilities and compliance gaps, document findings, and prepare executive reports. Lead client kickoff and debrief meetings, manage assessment communications, and provide remediation guidance. Investigate escalated security incidents, analyze root causes, maintain case documentation, and collaborate with SOC, IT, engineering, and senior security teams.

Leads people strategy across operating companies, advising senior leaders on workforce planning, organizational design, compensation, engagement, employee relations, compliance, HR analytics, change management, leadership development, and onboarding. Partners with HR Centers of Excellence to execute enterprise policies, resolve complex cases, manage risk, and build organizational capability. Supports multiple business units and drives strategic HR initiatives aligned with business objectives.

Run complex enterprise sales cycles from prospecting through close, manage a book of business, engage technical and executive stakeholders, drive customer adoption, refine sales processes, represent customer needs in product discussions, mentor Account Executives, and partner with marketing. The role requires enterprise B2B SaaS sales experience, preferably selling developer tools or similarly technical products, strong quota performance, technical acumen, and startup adaptability.

Manage a caseload of litigated claims, develop defense strategies, attend depositions, hearings, and mediations, analyze discovery and medical records, research legal issues, investigate parties and worksites, and draft briefs, memoranda, and client updates. The role requires substantial deposition experience, Illinois bar licensure, strong organizational skills, deadline management, independent judgment, and effective teamwork. Toxic tort experience is preferred, and applicants must submit a writing sample.

Leads the endpoint defense function across Cortex XDR, Microsoft Defender for Endpoint, Trend Micro, and related tooling. Owns endpoint coverage, policy tuning, telemetry quality, platform integration, incident containment support, automation, security KPIs, and team development. Partners with Cyber Defense and SIEM/SOAR teams to improve prevention, detection, remediation, and operational consistency across a heterogeneous endpoint fleet.

The Director will advise executives and people leaders while building leadership development, learning, performance management, employee relations, organizational effectiveness, and change-management programs. Responsibilities include coaching leaders, developing HRBP frameworks, supporting workforce planning and organizational design, guiding succession and talent decisions, using people data to identify risks, and leading cross-functional initiatives that improve culture, employee experience, leadership effectiveness, and organizational performance.

Own the full lifecycle of AI products, from discovery and requirements through launch, adoption, and continuous improvement. Define product strategy, roadmaps, backlogs, KPIs, and investment priorities while partnering with engineering on architecture and implementation trade-offs. Align technical and executive stakeholders, challenge assumptions constructively, and drive scalable B2B and B2C product solutions across a 30+ engineer AI organization.

Performs insurance, third-party administrator, reinsurance, and mortgage investment accounting. Responsibilities include journal entries, general ledger reconciliations, financial statement analysis, regulatory and audit schedules, treaty review, reporting, and process improvements. Collaborates with IT, Actuarial, Legal, and other departments on accounting initiatives and system enhancements.

Designs, configures, implements, tests, and analyzes o9 supply chain planning solutions. Partners with clients and internal teams to gather requirements, transform business logic into technical designs, build datasets, perform forecasting and optimization, execute testing, resolve solution gaps, and support deployment. Delivers stakeholder training, communicates project progress, mentors junior analysts, and contributes to full lifecycle enterprise implementations.

Paid 10-week internship introducing rising seniors and graduate students to sales and client management in the employee benefits insurance industry. Interns will explore prospecting, quoting, selling, enrollment, onboarding, and relationship management; complete assigned business projects, job shadows, workshops, networking, and a capstone presentation. The role requires approximately 40 hours per week during regular business hours.