Top Tech Jobs & Startup Jobs in Chicago, IL

Lead Reprise’s marketing function and redesign its B2B go-to-market approach with an AI-first strategy. Own pipeline generation, demand generation, ABM, content, events, partnerships, analyst relations, social media, marketing tooling, budget, and external partners. Set and achieve monthly pipeline targets, establish category leadership in demo automation, optimize program spending, and combine strategic leadership with hands-on execution.

Own end-to-end B2B SaaS sales cycles in global markets, selling to technical buyers and senior managers. Generate pipeline through outbound prospecting, lead discovery and qualification, manage forecasts in CRM tools, and lead POVs or POCs. The role requires consultative selling, autonomy, strong deal progression, and collaboration across flexible US and Israeli time zones in a fast-paced startup environment.

Lead developer relations as the company’s first DevRel hire. Create technical content, demos, examples, and projects; speak at conferences, meetups, and podcasts; build relationships with engineering teams and technical communities; gather product feedback; establish the company as a leading voice in AI-driven engineering; and grow its social following.

Lead client engagements on benefits strategy, plan design, open enrollment, and administration. Stabilize operations, manage carriers/brokers, execute transitions and platform migrations, ensure compliance, advise on cost optimization and multi-state/global expansion, and expand client relationships.

Own the organization’s end-to-end YouTube strategy, including channel architecture, content cadence, audience growth, editorial direction, packaging, analytics, experimentation, and monetization. The role partners with production, creative, marketing, social, and partnerships teams; develops growth playbooks and performance reporting; identifies revenue opportunities; tracks platform and creator trends; and coaches teams on YouTube best practices.

Designs, manages, and optimizes CI/CD pipelines; builds and maintains scalable, secure AWS infrastructure; and partners with development teams to support efficient agile deployments. The role requires extensive DevOps experience, AWS expertise, Docker and Kubernetes proficiency, advanced English and Spanish communication skills, and a focus on resilient, high-performance engineering.

Leads and mentors an engineering team building scalable web applications for fintech and media products. Responsibilities include setting technical architecture, guiding engineering decisions, partnering with product and design stakeholders, maintaining modern web applications, improving reliability and performance, supporting delivery planning, and adopting AI-assisted development and automation. The role combines hands-on software engineering, people management, technical strategy, and cross-functional collaboration.

Partners with sales, engineering, vendors, and customers to define warehouse robotics solutions. Leads technical discovery, site visits, system design, ROI modeling, proposals, test plans, and executive presentations. Supports solution scoping, WCS/WMS integrations, statements of work, MSA negotiations, implementation planning, and post-sale technical advising while feeding customer insights to Product.

Cultivate and steward a portfolio of 350–600 mid-level donors, securing $6,000–$10,000 gifts and developing prospects for major giving. Build personalized donor relationships, manage qualification and cultivation pipelines, use segmentation and engagement metrics, maintain CRM records, and communicate organizational impact. The role requires regular U.S. travel, cross-functional collaboration, and expertise in charity: water’s programs and WASH issues.

Lead the architecture, development, optimization, and operation of production LLM and AI automation systems. Design capabilities including agents, retrieval, code generation, tool use, model routing, evaluation, and observability. Drive platform modernization, scalability, reliability, architecture, and code quality while mentoring engineers and influencing technical practices across teams. Build prototypes, establish engineering standards, conduct reviews, and communicate complex technical concepts through documentation and cross-functional collaboration.