Top Tech Jobs & Startup Jobs in Chicago, IL

Run Discovered Labs’ founder-led content operation across LinkedIn and YouTube, from topic selection and editorial development through publication and performance analysis. Responsibilities include shaping founder content, coordinating external partners, repurposing long-form material, improving AI-supported content systems, and using engagement and pipeline data to guide editorial decisions. The role requires strong editorial judgment, hands-on execution, social content expertise, and the ability to work autonomously in an AI-forward, remote environment.

Lead end-to-end annotation projects: define workflows, coordinate teams (annotators, reviewers, experts), track progress and quality via dashboards, manage launches and phase transitions, pilot tooling and methodology improvements, and build scalable operational systems and documentation to support annotator community and cross-functional alignment.

Partner with senior leaders and managers on organizational design, workforce planning, talent development, performance management, employee relations, compensation cycles, and change management. Coach leaders, improve People programs, use Rippling and AI-enabled tools to analyze workforce data, and turn organizational insights into practical improvements across the employee experience.

Retain customers considering cancellation or downgrade through consultative conversations, objection handling, personalized recommendations, and targeted save offers. Resolve underlying issues with cross-functional teams, document cancellation reasons, monitor retention metrics, and support process improvements. The role requires strong communication, negotiation, analytical judgment, product knowledge, and experience meeting retention or quota-based goals.

Supports marketing through email campaign execution, social media content management, lead research and qualification, CRM database maintenance, website updates, blog publishing, and inbound lead routing. The role collaborates on marketing and business development projects while maintaining data accuracy and meeting deadlines. It is a fully remote, full-time position with opportunities for growth.

Own a portfolio of 50+ school districts, leading onboarding, staff activation, dashboard training, troubleshooting, adoption campaigns, and ongoing engagement. Analyze district data and activation trends, identify capacity risks, document account activity, and tailor support strategies. Deliver trainings and info sessions for school staff, collaborate cross-functionally, and use AI tools to create materials, analyze trends, and prioritize human support for districts needing intervention.

Own end-to-end product design for multiple AI-powered client and internal products, including user research, ideation, UX, and UI design. Collaborate directly with users, clients, and engineers, participate in product direction meetings, and independently design AI applications and Next.js products. The role offers ownership, exposure to diverse industries, and potential progression into a Design Lead position.

Develop, operate, and scale Proofpoint’s production infrastructure across global data centers and public cloud. Responsibilities include deployment, maintenance, troubleshooting, performance tuning, monitoring, alerting, capacity planning, incident response, infrastructure architecture, automation, and security. The engineer will collaborate with product and engineering teams, investigate complex system and network issues, support product rollouts, and participate in a 24x7 on-call rotation.

Lead Picus’s cybersecurity product marketing strategy and positioning. Develop differentiated messaging, value propositions, category narratives, thought leadership, executive presentations, sales enablement, and competitive guidance. Partner with the CTO, product, research, sales, and marketing teams to translate complex security research and innovations into compelling customer-facing stories. Monitor market and analyst trends, validate messaging with stakeholders, and refresh corporate and portfolio narratives quarterly.

Drive enterprise sales of Axway’s integration software, including MFT, API, and managed cloud solutions. Build and expand customer relationships, create sales pipelines, manage lengthy B2B sales cycles, exceed quotas, and lead executive-level product presentations. Partner with Product, Presales, Services, Support, Customer Success, and Marketing teams while selling across healthcare, supply chain, banking, and public-sector accounts.