Top Tech Jobs & Startup Jobs in Chicago, IL

Develop product messaging, positioning, go-to-market strategies, launch plans, enablement materials, and marketing campaigns for AI-powered legal technology. Gather customer and market insights, analyze product marketing metrics, support adoption, and collaborate with Product, Sales, Customer Success, and Marketing teams to improve product-market fit and commercial performance.

Provide onsite and virtual training, coaching, and go-live support for healthcare clients implementing athenaNet. Facilitate mock go-lives, prepare training materials, guide users on best practices, support provider workflows, and manage client-specific training deliverables. The role requires strong communication, independent judgment, organization, frequent domestic travel—up to 90%—and the ability to manage unpredictable schedules and extended onsite assignments.

Drive AI-enabled product strategy and execution by identifying customer opportunities, defining requirements, and partnering with engineering, design, data, sales, marketing, and customers. Lead development of products using LLMs, generative AI, RAG, and intelligent agents; validate roadmap priorities, communicate product vision, support launches, and improve feature adoption. Apply AI tools to accelerate product specifications, workflows, and software delivery.

Build, maintain, and optimize CI/CD pipelines, cloud infrastructure, and automated deployment workflows across AWS and Azure. Manage Docker and Kubernetes environments, implement GitOps with ArgoCD, automate provisioning with Ansible and AWX, administer Linux and Windows systems, and support release engineering. Develop scripts, monitor system health, apply security policies, troubleshoot production issues, and collaborate with development, QA, and operations teams to deliver reliable software releases.

Own the technical sales process for enterprise healthcare SaaS deals, partnering with account executives on discovery, tailored demos, proof-of-concept environments, integrations, security questionnaires, RFPs, and executive presentations. Engage health system leaders, translate clinical workflows into solutions, support business cases, certify sellers, document handoffs, and provide product feedback. The role is remote within the U.S. Central or Eastern time zones with occasional travel.

Own the full sales cycle for virtual academic support programs, from prospecting school districts and charter networks through contract negotiation and closing. Build pipeline, execute sales strategies, conduct presentations and demonstrations, consult with administrators, identify at-risk deals, and collaborate on onboarding and implementation. The role also involves refining sales processes, sharing market insights, supporting product improvement, and traveling occasionally to conferences or partner schools.

Own the complete technology function for a peer-to-peer fundraising platform as its sole engineer. Responsibilities include setting the technical roadmap, managing payment processing and reconciliation, shipping AI features, improving testing and deployment practices, addressing fraud and abuse, controlling infrastructure costs, communicating with non-engineers, and owning uptime and incident response. The role requires strong production experience with financial systems, PostgreSQL, LLM features, engineering-process improvement, and independent technical ownership.

Independently manage complex, high-value, multi-state Workers’ Compensation and occasional General Liability audits. Investigate disputes, interpret state-specific regulations and policy terms, reconcile audits for accuracy and compliance, and apply NCCI and WCIRB standards. The role also supports teammates, explains technical findings to customers and partners, and improves audit quality, efficiency, and processes.

Win new mid-market SaaS customers among high-volume employers. Build outbound pipeline, manage full-cycle consultative sales, run discovery and demos, develop business cases, negotiate contracts, maintain accurate HubSpot forecasts, and consistently meet quarterly and annual quotas. Sell to HR, talent acquisition, and operations leaders while partnering with marketing, partnerships, customer success, and implementation teams.

Build and operate distributed cloud backend services powering AI connections, collaboration, authentication, billing, telemetry, and developer workflows. Responsibilities include designing APIs and data models, writing Rust services, managing cloud infrastructure, leading projects, resolving production issues, participating in on-call, and guiding technical decisions across the team.