Top Tech Jobs & Startup Jobs in Chicago, IL

Architects, builds, and operates resilient backend services, cloud infrastructure, automation tools, and self-service interfaces supporting MDR and incident response operations. Partners with security practitioners and engineering teams to translate operational needs into scalable solutions, establish CI/CD and observability practices, improve reliability, and integrate AI-driven workflows. The role also provides technical mentorship, leads architecture and design decisions, and drives complex initiatives through iterative delivery.

Architect and operate scalable cloud and virtualized lab platforms for global sales engineering teams. Build automated cybersecurity demonstrations simulating malware, exploit paths, and detection workflows. Lead self-service tooling, product demonstration readiness, infrastructure reliability, outage resolution, security governance, and major conference technical operations. Partner with Product Management, Engineering, Information Security, and Platform Engineering while providing technical leadership across complex infrastructure initiatives.

Leads vulnerability intelligence research focused on rapidly analyzing and exploiting newly disclosed or actively exploited vulnerabilities. Develops Metasploit modules and framework improvements, conducts zero-day research, publishes technical analyses, advises detection teams, supports emergent threat response, presents research publicly, and mentors other researchers. The role requires advanced exploitation, reverse engineering, operating system, networking, and exploit mitigation expertise, plus cross-functional communication during time-sensitive security events.

Collaborate with GuidePoint Security and regional partners to drive Rapid7 solution adoption and revenue. Deliver technical training, product demonstrations, proof-of-concept evaluations, and sales enablement for partner engineers and sellers. Explain technical value propositions to technical and non-technical audiences, support partner-led opportunities, create enablement plans, and coordinate with Partner Account Managers. The role requires frequent travel to strategic partners nationally and is limited to East Coast residents.

Leads Rapid7’s global technical sales organization across Sales Engineering Specialists, Forward Engineering, Labs, and the Center of Excellence. Develops technical sales strategy, organizational roadmaps, succession frameworks, and engineering capabilities while partnering with sales leadership. Oversees integrations, demo infrastructure, enterprise platform architecture, ROI modeling, resource planning, and cross-functional execution. Drives organizational scaling, executive alignment, talent development, and measurable contributions to revenue and product innovation.