Top Sales Jobs in Chicago, IL

Lead and scale the Enterprise AI & Digital Natives sales segment in the NYC region. Own revenue targets, recruit and mentor a field sales team, advise CTOs and engineering leaders on Cloudflare solutions (Workers AI, R2, network security), drive new logo acquisition and account expansion, partner with Product/Customer Success/Solutions Engineering for go-to-market execution, and personally help close complex, high-value enterprise deals.

Responsible for driving growth by managing enterprise clients and acquiring new accounts, with a focus on complex sales cycles and customer engagement.

Lead DoD-focused account strategy and sales for Combatant Commands (COCOM/STRATCOM/TRANSCOM). Develop account plans, drive multi-year pipeline, negotiate contracts, navigate federal procurement vehicles, work with system integrators and partners, and position Cloudflare security and cloud networking solutions to meet mission objectives.

Serve as a quota-carrying technical trusted advisor managing the full customer lifecycle: discovery, architecture, demos/PoCs, onboarding, adoption, and expansion. Drive technical engagements, present to stakeholders, automate routine tasks with AI, and evangelize Cloudflare technologies externally.

The GTM Specialist drives Cloudflare One revenue by advising sales leaders, supporting strategic deals, and fostering partner relationships, requiring deep technical knowledge and strong consultative selling skills.

This role involves leading high-stakes account sales, engaging with C-suite executives, and expertly managing enterprise-level solutions while exceeding sales targets and fostering digital transformation.

The Senior Named Account Executive manages key enterprise accounts, drives growth through consultative sales, and fosters relationships with C-suite clients to achieve sales targets.

The Senior Named Account Executive will drive growth through strategic sale cycles, manage customer relationships, and lead complex sales negotiations in enterprise environments.

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.

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.