Top Tech Jobs & Startup Jobs in Chicago, IL

Provides high-touch technical support to enterprise clients through phone, chat, community portals, and escalations. Troubleshoots complex issues involving access management, connections, reporting, and syndication; documents solutions using KCS practices; and leverages AI and automation to improve efficiency. The role manages support queues and KPIs, collaborates across teams, supports onboarding, develops product expertise, and provides feedback to Product and Engineering.

Serve as lead legal advisor to product, engineering, and technology teams on AI, software, cloud, privacy, cybersecurity, intellectual property, and technology transactions. Develop AI governance and responsible-use policies, assess regulatory and ethical risks, negotiate technology and AI vendor agreements, advise on IP and data workflows, monitor global technology regulations, and train employees. The role requires significant legal experience, active bar membership, AI and privacy expertise, and the ability to influence executive and cross-functional stakeholders.

Drive net-new enterprise SaaS revenue across Fortune 500 CPG, retail, and e-commerce organizations. Build and manage high-value pipelines using Salesforce and MEDDPICC, develop strategic account plans, conduct consultative executive-level selling, negotiate complex contracts, and collaborate with Solutions Consulting, Customer Success, Product Marketing, and Legal. The role requires expertise in e-commerce and digital marketing, enterprise deal cycles, value selling, and structured sales methodologies.

Deliver live onboarding and sales training for Inside Sales and APAC teams. Partner with sales leaders to identify skill gaps, analyze Gong call data, and develop localized coaching, playbooks, and micro-learning content. Track onboarding milestones, certification, and ramp time while collaborating with Product, Marketing, and Revenue Operations. Apply AI and modern enablement tools to improve training workflows and seller performance. This is an autonomous individual contributor role requiring strong sales enablement experience and executive presence.