Top Tech Jobs & Startup Jobs in Chicago, IL

Build and automate secure, reproducible cloud infrastructure and tooling to support adversarial testing of AI systems. Collaborate with red teamers and engineers to reproduce, remediate, and simulate attacks, perform threat modeling and security reviews, and integrate security across the development lifecycle.

Full-cycle quota-carrying Account Executive selling Bold Metrics' SaaS fit and sizing solutions to apparel brands. Own outreach through contracting, build ROI cases, manage cross-functional coordination, develop outbound strategies, leverage AI to scale workflows, track funnel metrics, and feed customer insights to Product.

Design intuitive mobile and web experiences, build scalable Figma component libraries and design systems, create visual and motion assets for product and marketing, collaborate with Product and Engineering, mentor designers, and establish design standards and workflows.

Lead EDI architecture and implementation using Oracle and Cleo platforms. Design scalable B2B integrations, manage communication protocols (AS2, SFTP, HTTPS, API), create EDI maps (X12, EDIFACT), onboard trading partners, integrate with ERPs, optimize processes, lead UAT, and provide Tier 3 support and mentorship.

Drive new customer acquisition by building relationships with business owners, dealers, and service providers across North America. Lead consultative sales conversations, close memberships, meet/exceed KPIs and quotas, and collaborate with teammates to improve processes, messaging, and business development outcomes.

Close large, complex enterprise healthcare deals across health systems and MSOs. Carry new-business and expansion quotas, prospect to build a 3x pipeline, run 90-day pilots and convert to enterprise rollouts, build C-suite relationships, own ROI/business case and forecasting, navigate legal/security/procurement, and coordinate handoff to implementation and customer success. Travel 30–50%.

Design and build internal platforms, tooling, and AI-powered workflows to reduce developer friction, improve velocity, quality, and reliability. Partner with product, infra, and security to create reusable paved paths, measure impact with engineering metrics, and help define the Developer Experience practice.

Lead a full-stack engineering team, balancing hands-on coding and technical leadership. Partner with Product to align priorities, drive quality practices, hire and coach engineers, improve engineering processes, contribute to the codebase, and ensure scalable, testable, and user-focused product delivery.

Serve as outsourced accountant and financial advisor for a portfolio of schools. Manage full-cycle accounting (AP, payroll, grants), close books, prepare monthly financial statements, support annual audits and 990 preparation, liaise with authorizers/SEAs, analyze and model financial issues, and provide high-quality client service while supporting internal team growth.

Manage top-of-funnel outbound for Sapio Sciences: build prospect lists, run multi-touch outreach, lead consultative discovery calls, maintain HubSpot CRM hygiene, qualify opportunities for AEs, and feed market intelligence to Marketing and Product.