Top Tech Jobs & Startup Jobs in Chicago, IL

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.

Supports customers using Rapid7’s Vector Command Red Team service through attack surface analysis, reconnaissance, OSINT, reporting, customer communications, and request prioritization. The role coordinates with Red Team, MDR, and MVM teams; conducts manual network and service reconnaissance; develops scripts to analyze attack surface data; monitors customer exposures; and performs entry-level external penetration testing. It also includes customer onboarding, monthly reporting, update calls, and translating technical security concepts for nontechnical stakeholders.

Drives Rapid7 solution adoption and joint revenue growth through CDW by delivering technical demos, proof-of-concept evaluations, training, enablement plans, and solution guidance. Partners with account managers, sales engineers, sellers, and customers to support opportunities, explain technical value, resolve complex questions, and strengthen channel relationships. Requires consistent travel to CDW headquarters in Chicago and partner offices.

Leads strategy, roadmap, and execution for Rapid7’s SIEM and threat detection products. Translates customer, market, and competitive insights into prioritized capabilities for data ingestion, detection, search, and reporting. Aligns global engineering, detection science, SOC operations, marketing, sales, and customer success teams while driving delivery excellence, data-backed decisions, and improvements to the MDR customer experience.

Leads product strategy, roadmap, and execution for Rapid7’s managed detection and response portfolio, Endpoint agent, and SOAR/response capabilities. Aligns SOC Operations, Engineering, Detection Science, Vulnerability Research, Customer Success, Sales, and Marketing teams. Translates customer needs, operational data, market intelligence, and emerging AI and automation opportunities into prioritized improvements that enhance service quality, analyst efficiency, customer outcomes, retention, and growth.

Deploy and configure Rapid7 security products for post-sales customers, applying security best practices and documenting implementation decisions. Build custom dashboards, reporting workflows, integrations, and data pipelines using Python, SQL, and REST APIs. Support pre-sales scoping, resolve deployment challenges, collaborate across teams, improve internal delivery processes, and occasionally travel for customer engagements.

Conduct strategic and financial analysis, evaluate market opportunities and M&A targets, build valuation models, support due diligence, research competitors, and prepare executive and Board presentations. The role partners with business leaders on product strategy, market entry, competitive positioning, operational improvements, annual planning, and long-range transformation initiatives.