Top Tech Jobs & Startup Jobs in Chicago, IL

Own and improve 15Five’s AWS and Kubernetes infrastructure, databases, CI/CD pipelines, observability, reliability, disaster recovery, security operations, and AI platform. The role includes incident leadership, on-call participation, infrastructure automation with Terraform and Ansible, PostgreSQL administration, access and secrets management, compliance support, and cross-functional project delivery. This remote position requires strong ownership, communication, and the ability to independently deliver infrastructure, security, reliability, and AI governance initiatives.

Own a territory and manage the complete outbound sales cycle for Adapt, an AI-powered dynamic pricing product. Prospect property management company leaders, deliver revenue business cases, run pilots, negotiate contracts, close deals, attend regional events, and relay customer feedback to product teams. The role is remote within a territory and requires regular travel. The successful candidate will help establish the sales process as the founding seller in the region.

Supports People Operations and IT logistics for a remote company, including equipment shipping and tracking, onboarding and offboarding coordination, HRIS and ATS data maintenance, documentation, timecard and I-9 support, and general administrative projects.

Own a product pod end to end, including discovery, strategy, roadmap, delivery, customer research, and business outcomes. Manage and coach two experienced Product Managers, align multiple pods around a unified product strategy, and lead platform work involving integrations, customer data architecture, workflows, and customer-facing experiences. The role also advances AI transformation across product, design, and engineering while partnering with executives, customers, agency teams, and technical stakeholders.

Lead product design direction across complex, multi-team healthcare platform areas. Shape product strategy, experience architecture, design systems, and scalable experiences for patients, providers, and practices. Partner with product, engineering, data, and leadership to resolve ambiguity, guide execution, mentor designers, and raise quality. Establish AI-native design and engineering workflows using emerging tools such as Cursor and Claude Code.

Own strategic enterprise SaaS accounts from relationship-building through close and rollout. Build C-suite relationships, identify buying windows, maintain accurate forecasts, develop financially grounded business cases, structure conversion-focused pilots, and coordinate internal teams. The role requires long-horizon account development, complex multi-stakeholder selling, executive presence, and experience reopening previously lost accounts. Experience in logistics, supply chain, delivery technology, retail, or last-mile operations is advantageous.

Own end-to-end sales across K-12 school districts in designated territories. Build executive relationships, develop territory strategy and pipeline, navigate procurement and legal processes, lead consultative sales cycles, represent Marble in field meetings and conferences, and partner cross-functionally to drive implementation, adoption, expansion, and quota attainment.

Leads the Operations Strategy enablement roadmap and manages complex, cross-functional initiatives from business-case development through implementation, adoption, and measurable impact. Identifies scalable tools, technologies, automation, and operating practices across operational functions. Partners with Product, Technology, Analytics, Risk, Compliance, and Operations to define requirements, establish governance, manage dependencies, measure results, and provide recommendations to senior leadership.

Own the full sales cycle in the Chicago territory, from prospecting and pipeline development through contract negotiation and closing. Build relationships with small businesses, conduct market research, execute cold outreach, communicate product value, meet sales quotas, advocate for customer and product needs, and represent Justworks at networking events and trade shows. The role requires 25% travel within the Chicago and Greater Chicago area.

Leads Rapid7’s global technical sales organization across Sales Engineering Specialists, Forward Engineering, Labs, and the Center of Excellence. Develops technical sales strategy, organizational roadmaps, succession frameworks, and engineering capabilities while partnering with sales leadership. Oversees integrations, demo infrastructure, enterprise platform architecture, ROI modeling, resource planning, and cross-functional execution. Drives organizational scaling, executive alignment, talent development, and measurable contributions to revenue and product innovation.