Top Tech Jobs & Startup Jobs in Chicago, IL

Leads Rundoo’s Implementation team, owning customer go-live performance, ARR attainment, resource allocation, forecasting, operating cadence, escalation processes, coaching, and cross-functional collaboration. The role builds scalable, client-centered implementation processes, improves forecast accuracy and capacity planning, and establishes accountability across Implementation Managers. Requires Chicago-based office work at least four days weekly and experience leading post-sale teams with measurable delivery or revenue targets.

Provides functional product expertise and subject matter guidance for Coupa’s Intake and Orchestration offerings during pre-sales engagements. Supports demonstrations, prospect meetings, sales enablement, product direction, demo content, webinars, and marketing collateral. Requires strong knowledge of business spend management, applications pre-sales experience in SaaS, excellent communication, mentoring ability, a bachelor’s degree, and up to 50% domestic travel.

Leads a team managing ADA and PWFA accommodation claims, ensuring accurate, timely, compliant claim adjudication and strong customer service. Responsibilities include coaching employees, managing performance and workloads, reviewing claim files and calls, identifying process improvements, administering concurrent disability and leave claims, mitigating risk, and communicating operational updates. The role requires disability or absence management expertise, sound judgment, knowledge of applicable regulations, and effective stakeholder collaboration.

Owns enterprise sales across Fortune 500 and Global 2000 accounts, including prospecting, territory planning, business-value discovery, executive selling, competitive displacement, complex deal management, forecasting, closing, expansion, and renewals. The role requires selling multi-product platforms, coordinating internal and customer stakeholders, building business cases, and managing enterprise deals lasting nine to eighteen months. Approximately 30–40% travel is required.

Lead end-to-end customer deployments for an early-stage AI platform: scope, run discovery, manage multi-threaded projects, coordinate product/engineering, drive configuration/migration, support change management, inform product, build repeatable playbooks, and support sales and expansion while ensuring stakeholder alignment and successful adoption.

Leads a global Windows infrastructure engineering team supporting on-premises and Azure compute environments. Responsibilities include people leadership, project and incident delegation, change governance, escalation management, vulnerability remediation, roadmap development, technical debt reduction, licensing management, and operational SLA oversight. The role also requires hands-on expertise with Windows Server, Azure or AWS, infrastructure automation, PowerShell, Active Directory, MECM/SCCM, virtualization, hybrid cloud architecture, and technical documentation.

Leads the Midwest sales organization by developing and executing growth strategies, coaching sales teams, strengthening customer and supplier relationships, and managing regional revenue, margins, profitability, expenses, and strategic initiatives. Partners with Marketing, Finance, Operations, Procurement, and Category Management to improve customer experience, inventory planning, market expansion, and operational performance. Oversees talent planning, succession, performance management, and change leadership across the region.

Build the core AI platform for an AI-native trading experience. Develop a high-performance Rust backend supporting streaming responses, low-latency tool execution, caching, and model orchestration. Design secure, observable APIs and runtime components with authentication, authorization, rate limiting, auditing, tracing, retries, and fallbacks. Build safe trading action infrastructure with deterministic previews, confirmations, idempotency, and audit logs while partnering with product and frontend teams.

Paid, onsite summer cybersecurity and information security internship supporting project-based assignments at the Federal Reserve Bank of Chicago. Interns work 40 hours weekly for 10–12 weeks, analyze data, communicate findings, present information, and collaborate with internal stakeholders. Applicants must be current students graduating December 2027 or later, meet GPA requirements, and be authorized to work in the United States without visa sponsorship.

Own a mixed portfolio of grocery retailer accounts, managing onboarding, retention, expansion, account health, and long-term partnerships. Deliver data-driven account reviews, interpret performance data, identify churn risks, and tailor high-touch or scaled engagement models by account value. Collaborate with analytics, product, marketing, and operations teams to improve retailer outcomes. The role also requires public speaking, project management, creative problem-solving, and travel of up to 20%.