Top Tech Jobs & Startup Jobs in Chicago, IL

The GTM Engineer will design and maintain AI-powered workflows, integrate APIs, and ensure data quality while improving sales processes.

Lead complex enterprise sales cycles to acquire and expand multi-million dollar accounts. Architect territory and account plans, manage pipelines and forecasts, map customer IT architectures to Cloudflare reference architectures, lead virtual cross-functional teams, negotiate large contracts, and act as a trusted advisor driving digital transformation and long-term customer adoption.

Lead design and governance of global sales compensation plans and AI-native incentive frameworks. Architect metrics for consumption and AI monetization, drive C-level decisions, build AI tools for modeling and forecasting, and partner with Finance, HR, IT, Product, and GTM to enable accurate, auditable payouts and change management for global sales teams.

Embed with strategic enterprise customers to architect and implement complex cloud and web infrastructure migrations. Provide technical leadership on application and network security using Cloudflare Workers and Terraform, act as liaison to product and engineering teams, drive AI/LLM-enabled solutions, and remain a long-term trusted advisor for SASE and network security initiatives.

Drive sales to State and Local (SLED) public sector customers in Northern California. Build and execute territory/account plans, manage complex sales cycles and contract negotiations, maintain pipeline, and develop long-term strategic relationships to achieve revenue targets for Cloudflare services.

Drive new business acquisition, renewals, and expansion for Commercial accounts. Build and manage territory and pipeline, lead consultative technical-sales conversations, forecast and negotiate contracts, multi-thread into C-suite, and collaborate cross-functionally to ensure adoption, retention, and growth of Cloudflare solutions.

The Senior Solutions Engineer partners with sales to design solutions, deliver presentations, conduct demos, and support enterprise customer initiatives while focusing on Cloudflare’s product benefits.