Top Tech Jobs & Startup Jobs in Chicago, IL

Lead technology strategy, cybersecurity, infrastructure, compliance (HIPAA, NIST, SOC 2, HITRUST, FedRAMP), product security, cloud operations, vendor management, incident response, and AI governance. Oversee reliability, disaster recovery, secure development practices, audits, and cross-functional partnerships to support healthcare and public-sector customers.

Design intuitive web and mobile product experiences, contribute across feature areas, use and evolve the design system, prioritize shipping high-impact work quickly, collaborate with PMs and engineers, and demonstrate strong visual and interaction design via portfolio/case studies.

Drive new enterprise logo sales in an assigned Pacific Northwest territory for Keeper's cybersecurity platform. Build strategic plans and pipeline, prospect and qualify leads, deliver web demos, manage the full sales cycle from contact to close, negotiate contracts, forecast accurately, collaborate with legal, product, marketing and customer success, and travel up to 50% for customer meetings.

Lead enterprise external communications and strategic narrative for a regulated company. Drive regulatory, policy, customer, media, and revenue-aligned storytelling using AI and data-driven insights. Advise executives, coordinate cross-functional teams, manage reputational risk, and support go-to-market and stakeholder engagement.

Own and run the customer onboarding journey from post-sale through go-live and early adoption. Create implementation plans, remove blockers, coordinate cross-functional teams, drive time-to-value, ensure go-live readiness and handover to Customer Success, and improve onboarding processes.

Lead forecasting, budgeting, and financial modeling to support executive decision-making. Prepare management reports, variance analyses, and dashboards; partner with Accounting during close; improve forecasting and reporting processes; ensure data integrity and compliance; and present financial insights and recommendations to stakeholders and leadership.

The Customer Success Manager will manage post-launch relationships with enterprise customers, drive adoption and engagement, ensure renewals and upsells, and enhance customer value through collaboration with internal teams.

Lead IT Operations and IT Engineering for enterprise identity, endpoint management, network infrastructure, collaboration tooling, and end-user services. Set strategy, SLAs, roadmaps, and metrics; hire and develop a high-performing team; partner closely with Security, Finance, People, and Legal; drive AI-native automation and productivity tooling; own vendor relationships, budget planning, and major incident escalation and migrations.

Serve as Cvent subject-matter expert to configure, maintain, and optimize Cvent for multiple global clients. Provide strategic consulting, implement configuration changes, manage user roles/licenses, create training materials, support integrations, communicate with clients and internal teams, and drive process improvements while meeting SLAs and timelines.

Build and run your own outbound pipeline with phone-first prospecting. Identify decision-makers, run high-volume outreach, qualify prospects, and book qualified meetings for the CEO and CTO. Help shape messaging and the outreach playbook as the company scales.

Remote senior infrastructure engineer responsible for designing, implementing, and troubleshooting enterprise voice/unified communications (Cisco CUCM), VMware virtualization (vCenter/vSphere/ESXi) and Citrix (CVAD/DaaS) environments. Requires deep hands-on experience, multi-system troubleshooting, and delivery of infrastructure solutions.