Top Tech Jobs & Startup Jobs in Chicago, IL

Leads customer-facing technical discovery, architecture, demonstrations, evaluations, proofs of value, and technical close for Cloudflare One solutions. Advises enterprise customers on Zero Trust, SASE, secure connectivity, WAN transformation, AI security, and related technologies. Partners with sales, product, engineering, support, and customers to drive successful evaluations, communicate business value, create reusable technical assets, and provide feedback for product improvement.

Lead strategic enterprise sales for Cloudflare's largest accounts, closing multi-million-dollar platform deals. Own territory and account plans, forecast accurately, manage pipelines, engage C-suite executives, lead cross-functional virtual teams, map Cloudflare to enterprise architectures, and drive customers' digital transformation while consistently exceeding quotas.

Own mid-market territory sales by acquiring new customers, expanding and renewing existing accounts, building partner relationships, developing pipeline, communicating Cloudflare’s value, forecasting revenue, negotiating contracts, and driving adoption. The role requires engaging technical and executive stakeholders across security, networking, development, and infrastructure teams while coordinating with internal cross-functional groups.

Leads complex enterprise sales cycles for Cloudflare, driving new-logo acquisition, account expansion, multi-million-dollar quota attainment, forecasting, and strategic pipeline management. Builds executive relationships, maps customer IT architectures to Cloudflare solutions, leads virtual cross-functional teams, negotiates large contracts, and positions Cloudflare as a digital transformation partner. Coaches colleagues and serves as a trusted advisor to enterprise customers.

Leads technical relationships with strategic partners across pre-sales and post-sales activities. Develops joint go-to-market strategies, enables partner technical champions, supports solution discovery and proof-of-concepts, and drives adoption of Cloudflare One, Zero Trust, and AI solutions. Owns technical account plans, partner service delivery readiness, joint managed-service offerings, architectural health, performance metrics, and product feedback initiatives.

Drive Cloudflare One revenue and adoption as a consultative sales expert. Advise sales leaders on strategy and pipeline generation, present SASE and security solutions to strategic customers, enable account executives, support complex deals, engage partners, provide management business reviews, and communicate market feedback across product, marketing, enablement, and partner teams. The role requires strong cybersecurity and networking expertise, strategic planning, competitive knowledge, presentation skills, and 10–20% travel.

Lead global HR business partnering for R&D, Engineering, Product, Security, and Research organizations. Advise senior technical executives, align talent strategy with business goals, architect AI-native organizational structures, evolve career frameworks, manage succession and retention, guide complex change, and coordinate People Team centers of excellence. Lead a global HRBP team while applying people analytics and executive coaching to improve organizational health, leadership effectiveness, and workforce outcomes.

Own the end-to-end People lifecycle for M&A: lead HR due diligence, partner with Corporate Development, build cross-functional integration playbooks, orchestrate Recruiting/Comp/Immigration/Payroll workstreams, and design day-1 onboarding and retention programs to integrate acquired technical teams under compressed timelines.

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 strategic People Business Partner to R&D leadership, driving organizational design, workforce planning, talent management, change leadership, and AI-driven people insights to align workforce strategy with business goals.