Top Tech Jobs & Startup Jobs in Chicago, IL

Manage a portfolio of 15-30 active billing customers across CoreWeave infrastructure and Weights & Biases software. Drive retention, renewals, and expansion by building multi-threaded relationships, monitoring usage and account health, negotiating commercial deals, coordinating technical and cross-functional resources, forecasting revenue, and partnering with internal teams to deliver customer outcomes.

Own end-to-end product outcomes for an AI-first SaaS platform: set strategy and roadmap, conduct market and user research, define PRDs and user stories, collaborate with engineering, design, data, and customer success, and measure impact to drive growth.

Own end-to-end enterprise sales into large multifamily owners: prospect, demo, negotiate, close, launch and expand accounts. Spend significant face-to-face time in market, sell to C-suite, manage complex multi-threaded deals, partner with Customer Success and Product, and help build sales playbooks and processes.

Field-driven Territory Account Executive responsible for full-cycle, self-sourced sales: prospecting, in-person demos, closing deals, building pipeline and local partnerships, and managing Salesforce-driven pipeline to exceed quota across Square's product suite.

Lead strategy and execution for a tiered partner program: identify, qualify, and onboard partners; manage Tier 1/2 executive relationships; structure alliance deals; drive co-marketing and enablement; build partner performance dashboards; partner with sales, product, marketing, and legal; mentor junior team members and scale partner operations to drive joint revenue.

As an Infrastructure Engineer, you will develop and maintain systems, triage issues, and manage Linux environments, working both independently and as part of a team.

Design, build, and maintain scalable test automation frameworks and CI/CD-integrated pipelines. Lead functional, integration, regression, and performance testing across distributed systems and telephony platforms. Mentor engineers, analyze failures using logs/metrics, execute load/stress tests, and improve test infrastructure, reliability, and engineering productivity.

The Senior Account Executive will acquire new clients and expand existing accounts, focusing on B2B SaaS sales in the digital native sector.

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.

The IT Systems Engineer will manage IT operations, ensure security compliance, and oversee cloud infrastructure including AWS and DigitalOcean. Responsibilities include device management, help desk support, and implementing security policies.

Monitor and manage live production work using system tools and dashboards; make real-time capacity decisions, triage escalations, analyze performance data, propose corrective actions, document processes, create client production plans, and train or mentor operations staff.