Top Tech Jobs & Startup Jobs in Chicago, IL

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.

Write high-volume email campaigns and flows in Klaviyo for complex DTC brands. Translate retention briefs into persuasive promotional, educational, launch, and seasonal copy; develop creative concepts; create brand voice guides, email best practices, and AI workflows; review and coach other writers; and help establish and scale the agency’s dedicated copywriting function.

Leads customer growth marketing for a B2B SaaS product by driving feature adoption, customer expansion, trial conversion, and sales enablement. Responsibilities include launch communications, adoption programs, customer stories, account-based marketing, expansion deal support, usage reporting, customer research, and positioning insights. Partners closely with Product, Customer Success, Account Management, Sales, Demand Generation, and Operations teams while using AI tools and analytics to improve content, messaging, and growth programs.

Leads the KFC US site reliability engineering team responsible for cloud infrastructure, restaurant connectivity, in-store edge systems, reliability, security, compliance, and operational excellence. Oversees architecture, infrastructure as code, deployment automation, observability, incident response, vendor coordination, and continuous improvement. Develops engineers, establishes sustainable on-call practices, manages platform risks, and partners with technology, restaurant operations, cybersecurity, and global reliability leadership.

The Regional Sales Manager will generate new business and revenue among mid-market and enterprise employers. Responsibilities include prospecting, networking, event representation, pipeline management, lead qualification, negotiations, forecasting, CRM reporting, and meeting sales targets. The role requires consultative selling expertise in corporate wellness, healthcare, employer benefits, or SaaS and involves travel to multiple U.S. states up to 40% of the time.

IP Counsel will manage intellectual property risk through freedom-to-operate and invalidity analyses, advise on licensing and design-around strategies, support technology and research transactions, assist with patent prosecution, manage disputes and outside counsel, and develop the company’s IP program. The role partners with scientific, clinical, regulatory, commercial, and executive stakeholders and provides practical legal guidance supporting diagnostics and life sciences innovation.

Own and manage client relationships, make architectural decisions, run discovery and stakeholder interviews, deliver software or automations, and contribute intellectual property back to the practice.