Top Tech Jobs & Startup Jobs in Chicago, IL

Lead post-purchase lifecycle strategy for DTC/subscription brands across email and SMS. Build automated flows, retention systems, winback campaigns, cohort dashboards, and run A/B tests to increase LTV and reduce churn while partnering with Growth, CX, and Creative.

As a Senior Underwriting Consultant, you'll evaluate insurance applicants, assess risks, and make underwriting decisions that impact business success, while promoting a culture of innovation and career development.

Develop and apply optimization and valuation models for CPA's CAISO-exposed portfolio, particularly storage. Lead CRR strategy, support resource onboarding, analyze market/policy changes, produce executive reports, and implement continuous improvement in operations, reporting, and risk management.

Lead global cloud and SaaS operations to ensure availability, performance, incident response, and compliance. Manage distributed engineering, NOC, and incident teams; drive operational maturity, automation, cost optimization, vendor management, and cross-functional partnership with Security, Product, and Support.

Drive growth in strategic enterprise accounts by landing and expanding large, complex organizations. Lead C-suite discovery, manage long sales cycles and procurement, position Sweep as a mission-critical platform, build multi-year account plans, partner with Sales Engineering and Product on deal strategy, and maintain disciplined forecasting and pipeline.

Lead USCIS program delivery as single point of accountability: manage agile two-week sprints, integrated backlog, risk register, program artifacts, continuous monitoring/OA modernization, vulnerability/configuration management, security automation, audit readiness, stakeholder engagement, and ML/AI governance risk considerations.

Manage day-to-day global benefits administration (health, retirement, leave, voluntary) across US and international markets. Oversee enrollments, eligibility, vendor/platform relationships, renewals, compliance (ERISA, ACA, GDPR), leave/Workers' Comp, 401(k) operations, invoicing, and open enrollment. Drive data integrity, vendor performance, communications, audits, M&A benefits integration, and continuous improvement to enhance employee experience.

Work on development tasks for video delivery systems including ingest, DRM, adaptive bitrate formats, transcoding, and content delivery. Participate in development discussions, complete assigned tasks, and collaborate with QA, cloud, and front-end teams to deliver streaming video features.

Lead end-to-end product execution for a scalable, compliant de-identified EHR data platform. Define roadmap, prioritize ingestion/normalization/de-identification/modeling, embed AI-driven automation, ensure data quality and compliance, and drive cross-functional alignment for commercial research use cases.

Freelance Account Supervisor supporting healthcare PR for R&D/pipeline and clinical trial communications: develops messaging and materials, synthesizes media monitoring, manages smaller projects, collaborates cross-functionally, and mentors junior staff on project-based engagements.