Top Tech Jobs & Startup Jobs in Chicago, IL

Sell OutSystems enterprise AI development platform across a Northeast territory: prospect and close named accounts, build C-level relationships, manage complex sales cycles, partner with system integrators and channels, and achieve quarterly and annual quota.

Sell OutSystems AI development platform within a defined territory by prospecting, qualifying, and closing named accounts. Build C-level relationships, execute complex sales cycles, articulate business value/ROI, negotiate contracts, and collaborate with system integrators and channel partners to meet quarterly and annual quotas.

Lead the Competitive Intelligence practice by analyzing market dynamics, supporting sales strategies, and influencing product roadmap based on competitor insights.

Lead global technical strategy for OutSystems platform reliability and automation. Define security and data residency for AI agents, drive transition to Autonomous Platform Engineering, design a Platform Workbench to automate routine administration (60%+), and influence product management with field-tested AI infrastructure requirements.

Lead UX/UI Designer who partners with executives to design governed agentic workflows and enterprise UI. Owns end-to-end research, testing, UI design, agentic interaction models, design system governance, automation of design workflows, workshop facilitation, and mentorship. Focus on AI transparency, human-in-the-loop protocols, and building agent-ready design standards.

Lead end-to-end development of complex, production-ready agentic systems on the OutSystems platform. Implement secure, scalable AI/LLM integrations with vector databases, enforce governance and privacy, coach teammates on AI-native delivery, and serve as the team's quality gate.

Lead design and implementation of scalable sales processes, systems strategy, and cross-functional GTM programs. Own CRM and sales tech integrations, define KPIs, drive large technology implementations and change management, translate data into executive narratives, and deliver AI-driven revenue optimizations.

Design and validate scalable enterprise architectures and agentic systems using OutSystems and AWS/Bedrock. Translate business needs into maintainable applications and AI agents, define reusable architecture patterns, assess and modernize existing systems, identify nonfunctional requirements and integrations, mentor teams, and grow Professional Services technical capability through best practices and thought leadership.

Lead and develop a team of Technical Leads and Software Developers, overseeing performance management and technical delivery of solutions on the OutSystems platform.

Lead strategy for Government solutions at OutSystems, focusing on Product and GTM strategies. Engage with senior leadership and customers to drive business success and develop innovative AI solutions.