Top Tech Jobs & Startup Jobs in Chicago, IL

Enterprise Account Executive responsible for sourcing and owning pipeline, conducting opportunity assessments and value discovery, demonstrating ROI, navigating complex multi-stakeholder deals (CTO, VP Eng, FinOps), collaborating with Sales Engineering and Customer Success, maintaining CRM and forecast discipline, and closing negotiations to drive long-term customer value.

Leads Cast AI’s global marketing strategy, organization, budget, and operating model. Owns positioning, demand generation, pipeline, customer acquisition, product adoption, marketing efficiency, and revenue contribution. Builds an accountable, AI-enabled marketing organization spanning product marketing, digital, content, field, partner, lifecycle, customer, and marketing operations. Partners closely with executives, Product, Sales, Customer Success, and Revenue Operations across global markets.

Owns Cast AI’s commercial contracting function, negotiating sales, renewal, SaaS, vendor, reseller, partnership, NDA, SLA, EULA, and subscription agreements. Leads contracting process standardization for a growing multi-product business, advises on privacy, intellectual property, governance, and compliance, coordinates commercial disputes with external counsel, and supervises APAC legal resources. Partners closely with sales, customer success, deal desk, billing, support, and compliance teams.

Own the full sales cycle for Cast AI Database Optimizer: prospect, qualify, demo, run proofs of concept, build business cases, negotiate and close net-new enterprise and upper mid-market customers while partnering with Product and Engineering.