Top Tech Jobs & Startup Jobs in Chicago, IL

Leads instrumentation and controls engineering for large, multidisciplinary energy projects, including design reviews, specifications, control logic, alarm management, DCS/SIS integration, and vendor coordination. Supports FAT, PSAT, PSSR, commissioning, startup, and technical documentation. Requires extensive experience in refining, petrochemical, and related energy facilities, strong knowledge of instrumentation measurements and process control systems, and the ability to lead projects exceeding $150 million in total installed cost.

Leads and mentors an AI platform engineering team while contributing to production code, architecture, prototypes, delivery planning, and system reliability. Partners with Product and engineering leadership to define technical direction, resolve architectural issues, develop people, and deliver scalable AI-enabled software. The role combines people management with hands-on engineering and welcomes first-time line managers.

Own enterprise sales growth across Western U.S. territories and target verticals. Build pipeline, manage complex six- and seven-figure sales cycles, engage C-suite security and procurement stakeholders, develop partner-assisted opportunities, and maintain forecasts. Collaborate with Solutions Engineering, Marketing, Product, Partnerships, and Customer Success to close net-new and expansion deals involving identity verification and passwordless authentication solutions.

Leads technical solution architecture for military and federal health capture and proposal efforts. Designs secure, interoperable EHR, cloud, data, analytics, and DevSecOps architectures; authors technical volumes, graphics, compliance matrices, and presentations; estimates staffing and technical costs; supports demonstrations and proof-of-concepts; ensures security and compliance alignment; and mentors architects and subject-matter experts.

Drive new and expansion business across assigned enterprise accounts in the Midwest. Own account strategy, prospecting, pipeline development, quota attainment, executive relationships, solution presentations, negotiations, and deal closure. Coordinate cross-functional virtual teams, assess customer needs, escalate support issues, maintain customer satisfaction, forecast sales activity, update CRM records, and maximize revenue through expanded product usage. Travel approximately 50–75%.

Own the Payments & Checkout roadmap, improving checkout conversion, payment authorization, BNPL adoption, fraud-risk balance, vendor performance, and payment cost efficiency. Partner with engineering, design, data, processors, networks, wallets, and BNPL providers to optimize transaction growth, average order value, and completed payments. Use experimentation, SQL, and analytics to diagnose funnel performance and deliver measurable business outcomes.

Leads OuterBox’s internal AI strategy, AI engineering team, and development of client-facing AI services. Identifies market opportunities, converts internal capabilities into priced consulting offerings, oversees production deployments and partner programs, and drives AI adoption, training, and measurement. Partners with executives, clients, engineering, and technology teams on architecture, security, cloud governance, reliability, pricing, and ROI.

Executive leader responsible for Customer Experience program management strategy, portfolio governance, delivery standards, operational scaling, performance analytics, and cross-functional alignment. The role leads Associate Directors and program teams, establishes PMO frameworks, oversees complex initiatives, drives executive reporting and decision governance, and builds scalable processes, accountability structures, and leadership development programs.

Provides in-house legal support across commercial contracts, fintech regulatory matters, disputes, litigation, employment issues, M&A, privacy, governance, and cross-border transactions. Negotiates contracts, manages regulatory submissions and legal deadlines, advises internal teams and the risk committee, and coordinates outside counsel. Maintains and improves the Ivo contract and vendor database, develops contract reporting, aligns compliance workflows, and implements legal-process improvements.

Lead commercial and technology contracting, negotiating SaaS, API, data, AI, vendor, carrier, and partnership agreements. Advise on AI, privacy, data, IP, and technology risks; develop contract playbooks, templates, workflows, and training; oversee legal AI and contract management tools; and manage, mentor, and develop a contracts team. Support commercial disputes, litigation, and corporate projects as needed.