Top Tech Jobs & Startup Jobs in Chicago, IL

Build responsive web applications and scalable frontend/backend services, design secure APIs and databases, implement AI-powered search and asset management features, collaborate on system architecture, and optimize performance and UX for a cloud-native DAM platform.

Explains how to locate people on social media using reverse image and facial-recognition search, highlights limits of Google Images and TinEye, and recommends Face2social for matching faces across platforms, even from old photos.

Create original, SEO-optimized content (blog posts, website copy, product descriptions, social media) aligned with marketing goals. Collaborate with design, SEO, and marketing teams, edit and update content, maintain brand voice, meet deadlines, and improve content performance.

Advise as an outbound Playbook Architect: design multi-channel, intent-driven outbound sequences, write copy frameworks and AI prompt logic, and deliver ready-to-launch playbooks that maximize replies and booked meetings. Work asynchronously as an equity-bearing advisor while keeping a full-time job.

Lead AMER solutions advisory to support sales by demonstrating Icertis solutions, developing strategic CLM proposals, driving thought leadership and innovation, advising customers, and collaborating with sales and product teams to ensure adoption and satisfaction.

Own the full sales cycle for creators on Starter and Growth plans, including outbound prospecting, qualification, discovery, demos, objection handling, negotiation, and closing. Manage inbound leads, revive dormant opportunities, maintain CRM accuracy, forecast pipeline, meet revenue targets, and collaborate with Marketing, Onboarding, and Customer Success. The role is remote-first and suited to an early-career closer with outbound sales experience.

Build and scale backend APIs, services, event-driven workflows, queues, data models, caching, and integrations serving millions of users. Lead complex technical initiatives from discovery through production, improve reliability and performance, debug cross-system issues, and optimize databases and infrastructure interactions. Partner across Product, Design, Infrastructure, Platform, Data, and Support while mentoring engineers, influencing technical decisions, and raising engineering quality standards.

Develop and define Retool’s brand voice across websites, campaigns, content, events, and in-product experiences. Partner with design, marketing, product, engineering, and external agencies to translate complex technical concepts into clear, compelling copy. Establish voice and tone systems, maintain brand consistency, experiment with new language, provide creative feedback, and independently manage multiple projects in a fast-paced startup environment.

Own new-business sales to win employer and TPA customers: prospecting, outbound outreach, discovery, product education, end-to-end deal management, proposal/contracting, market feedback, and travel (20-50%).

Lead administration of Microsoft 365, Google Workspace, SaaS applications, Azure identity, and cloud infrastructure in a fully cloud-based organization. Provide Level 2/3 service desk escalation, execute migrations and cybersecurity projects, establish IT service processes, manage assets and vendors, and support onboarding, offboarding, incident response, change management, and M&A initiatives. The role partners with IT leadership and may help build and manage a growing internal technical team.