Top Tech Jobs & Startup Jobs in Chicago, IL

Lead Avantpage's integrated marketing function, developing go-to-market strategy, demand generation, product and brand marketing, and marketing operations. Drive pipeline and revenue growth, oversee analytics and CRM/automation, guide product launches and sales enablement, and manage a team of three while aligning cross-functionally with Sales, Client Services, Innovation, and Executive Leadership.

Manage and supervise full-charge bookkeeping staff; ensure timely completion of reconciliations, A/P, payroll, and financial reporting; review and approve client reports; provide training, client advisory on controls and process improvements; foster long-term client relationships and deliver exceptional service.

Manage full-cycle recruiting for commercial, federal, military, and state contracts, sourcing Physicians, healthcare professionals, and C-level executives. Build candidate relationships, draft and post job ads, screen and scout candidates, maintain assignment status, coordinate with managers, participate in meetings/training, and perform other duties to meet staffing goals in a fully remote role.

Design, build, and maintain payment integrations and a reconciliation data platform for high-volume restaurant transactions. Implement terminal-to-cloud flows, ingestion pipelines, matching engines, reporting UIs, and payment analytics. Provide technical leadership, documentation, and mentor teammates to ensure reliable settlement and reconciliation.

The Head of Paid Media will design and execute B2B paid media campaigns, manage budgets, optimize lead quality, and collaborate across teams to drive growth and brand awareness.

Lead and grow strategic cybersecurity alliances by managing executive relationships, driving partner-sourced pipeline and revenue, executing joint go-to-market initiatives, coordinating events and thought leadership, identifying new partnership opportunities, and collaborating with internal incident response, forensics, sales, and executive teams to position CYPFER as the preferred cyber incident response partner.

Lead QA for Salesforce-native products: create test plans and automated frameworks (Playwright), run manual/automated and performance tests, manage large Salesforce test data sets, integrate tests into CI/CD, identify bottlenecks, and mentor junior QA engineers while collaborating cross-functionally.

Manage, deploy, scale, and monitor OpenShift and Kubernetes clusters; configure and troubleshoot containerized applications; automate provisioning and deployment pipelines using Ansible, Terraform, and Helm; integrate clusters with CI/CD tools (Jenkins, Maven, GitHub/GitLab); document issues and support platform reliability.

Lead end-to-end payments fraud and dispute strategy, build AI-native risk operations, manage vendor/processor relationships, run investigations and chargeback economics, hire and develop analysts, and translate risk metrics to executive-level business impact.

Lead technical onboarding and ongoing support for remote connectivity at dental practices. Configure and troubleshoot VPNs, Splashtop, remote desktop, printers/scanners, and network authentication. Manage implementations, validate connectivity and integrations, coordinate with clients and third-party IT, escalate complex issues, document processes, and contribute to improvements in remote access infrastructure and automation.