Top Tech Jobs & Startup Jobs in Chicago, IL

Own strategic enterprise accounts and drive multi-million-dollar growth by advising executives on data, AI/ML, and cloud transformation. Lead account strategy, solution design, scoping, pricing, negotiations, delivery orchestration, and alliance co-selling with Google Cloud and other partners. Build relationships with Fortune 500 and Fortune 1000 clients, exceed sales quotas, close new professional services business, and connect technical solutions to measurable business outcomes.

Own the post-sale customer lifecycle, including onboarding, adoption, training, value reviews, feedback collection, and renewals. Serve as a trusted technical advisor to B2B technology and SaaS customers, advocate internally for issue resolution and product improvements, and engage stakeholders ranging from engineers to CTOs. Manage a broad portfolio of SMB through commercial accounts while helping customers optimize cloud infrastructure costs.

Leads and grows the engineering organization, sets technical strategy and roadmap, oversees execution across multiple teams, and provides technical direction on architecture, scalability, reliability, security, and quality. Partners with Product, Design, Operations, Risk, and the CTO to deliver customer-focused financial products. Responsibilities include recruiting and developing engineering leaders, improving processes, removing organizational bottlenecks, and balancing product delivery with long-term platform and infrastructure investments.

Own large-ticket commercial credit underwriting, including financial analysis, credit memos, committee presentations, delegated authority, escalations, leasing structures, syndication, portfolio policy, and automation. Build standards for capital-markets partners, manage exceptions and concentration risks, coach underwriters, and improve decisioning through bureau data, scorecards, and AI. The role requires personally signing $1M+ credits, handling complex commercial files, and developing scalable credit processes across multiple jurisdictions.

Manage revenue recognition and compliance under ASC 606 and GAAP. Review contracts and RFPs, establish standalone selling price frameworks, reconcile Oracle revenue to the general ledger, support financial close and audits, assess credit reserves, maintain internal controls, integrate acquired entities, conduct UAT, and improve revenue processes through automation and documentation.

Own the vision and strategy for an agentic AI-powered product that helps policymakers and military operators identify mission-critical information. Responsibilities include customer discovery, market research, roadmap and backlog development, user story creation, stakeholder engagement, cross-functional collaboration, and balancing NLP capabilities with infrastructure costs. The role partners with engineers, designers, data scientists, analysts, and customers to deliver user-centered functionality in Scrum or Kanban environments.

Leads integrated full-funnel marketing strategies for B2B clients, including positioning, ICP definition, go-to-market planning, demand generation, campaign integration, SEO, AEO, and AI-driven discovery. Owns client strategy, workshops, performance measurement, conversion optimization, and executive reporting. Collaborates with SEO, paid media, content, product, development, and project teams to connect marketing activity with pipeline, MQL, CAC, ROAS, and broader business outcomes.

Lead mechanical engineering design and execution for multiple capital projects from concept through construction administration. Responsibilities include developing calculations, technical reports, drawings, and specifications; directing and reviewing engineering staff; coordinating multidisciplinary teams; communicating with clients; conducting field surveys; reviewing submittals, RFIs, and change orders; and ensuring technical quality, budgets, and deadlines. Projects primarily involve healthcare, government, military, laboratory, corrections, and infrastructure facilities.

Own the vision, roadmap, data access layer, reporting templates, and query capabilities for Skylar Analytics. Partner with data engineering, data science, and adjacent product teams on data modeling, pipelines, anomaly detection, predictive alerting, and agentic AI integration. Lead go-to-market strategy, positioning, packaging, and customer value messaging for the analytics product.

Designs, configures, deploys, tests, troubleshoots, and validates complex enterprise network solutions. Develops implementation and test plans, assesses existing architectures, resolves technical issues, documents configurations and results, communicates project status and risks, and supports client knowledge transfer and operational transition. Collaborates with clients, project managers, sales, presales, engineers, and architects. Travel and onsite installation or data-center work may be required.