Top Tech Jobs & Startup Jobs in Chicago, IL

Senior Recruiter responsible for full-cycle hiring across sales, technical, and engineering roles. The role emphasizes structured interviewing, quality of hire, candidate closing, hiring-manager partnership, recruiting metrics, process efficiency, and recruiting infrastructure. It is initially remote as a contract position, with potential conversion to a full-time, on-site role in Menlo Park.

The Integration Engineer will design and maintain healthcare data integrations, collaborating with teams to optimize performance and improve reliability using Python and various standards.

Owns post-go-live relationships with health system customers, driving retention, adoption, measurable clinical and operational outcomes, executive business reviews, risk forecasting, and expansion into additional use cases. The role manages a named account portfolio, builds ROI cases, supports workflow change, and partners with Sales on commercial growth. It requires executive engagement with clinical, operational, and financial leaders and includes 25–40% travel.

Lead AI deployments for payor customers from planning through launch and adoption. Coordinate customer, product, engineering, clinical, and implementation teams; manage timelines, milestones, risks, training, rollout readiness, and stakeholder alignment. Translate payor workflows and business priorities into actionable plans, resolve blockers, guide organizational change, and develop repeatable deployment playbooks that improve scalability, adoption, and time to value.

Build, deploy, and operate production conversational AI agents for healthcare organizations. Responsibilities include designing RAG pipelines, developing tool-calling and MCP integrations with EHRs and enterprise systems, writing production Python, configuring monitoring, managing go-lives, troubleshooting incidents, and advising customers on AI architecture, reliability, safety, and capabilities.

Owns healthcare AI deployments from workflow discovery and solution design through configuration, integration, launch, adoption, and measurable impact. Maps clinical and operational workflows, determines automation opportunities, configures and tests agents using JSON, command-line tools, and version control, validates data, coordinates security and go-live activities, and builds impact dashboards. Partners with healthcare customers, executives, engineers, product managers, and clinical experts while managing complex technical and operational dependencies.

Leads the strategy, design, execution, and measurement of B2B events and executive experiences. Builds an integrated events calendar, connects programs to pipeline and revenue, develops account-based marketing personalization, manages budgets and vendors, and leads a lean team. The role oversees conferences, trade shows, executive dinners, roundtables, and Customer Advisory Boards while using AI agents and automation to scale engagement, follow-up, and event impact. Regular travel of 25% to 40% is expected.

Leads regional customer success for health system partnerships, managing Directors and senior Customer Success Executives. Owns executive relationships, enterprise implementations, clinical workflow integration, customer success metrics, retention and expansion sales. Builds scalable onboarding, training, change-management playbooks and operating frameworks while partnering with Product, Engineering, Clinical, and Sales teams to improve adoption, operational efficiency, patient outcomes, and net revenue retention.

Define and document a repeatable inbound AI methodology for healthcare. Partner with 5–7 health systems to design decision trees, IVR logic, provider directory mapping, and escalation rules. Translate workflows into product requirements, influence the Front Door roadmap, and enable deployment teams with playbooks, templates, and training so deployments scale without continuous oversight.

The VP of Enterprise Sales will manage strategic accounts, engaging C-suite executives, architecting deals, and driving software solutions to healthcare providers, while working with various teams to ensure client satisfaction.