Top Tech Jobs & Startup Jobs in Chicago, IL

Lead the design, implementation, and operation of Carefeed’s AWS cloud infrastructure. Build and maintain CI/CD pipelines, standardize logging, alerting, and observability tools, respond to production incidents, improve system reliability, and guide infrastructure and developer tooling practices. Collaborate with engineering, product, and business operations teams while owning complex infrastructure initiatives independently.

The Principal Engineer will lead architectural decisions, mentor engineers, write production-ready code, and design scalable systems to support growth.

Lead and scale a customer-facing technical support team for a B2B SaaS product in senior living. Own SLAs, KPIs, escalations, incident management, knowledge base, reporting, and collaboration with engineering to reduce recurring issues and drive product improvements. Hire, coach, and raise technical troubleshooting standards while delivering high-quality customer communication and operational metrics.

Own Carefeed’s marketing function, including demand generation, brand strategy, lead generation, thought leadership, events, messaging, marketing technology, and performance measurement. Build a scalable pipeline engine, align marketing with sales and BDR goals, establish channel and content strategies for the senior living ecosystem, and grow the marketing team in a fast-paced, venture-backed SaaS environment.

Own and close Carefeed’s largest enterprise SaaS deals across the West. Build executive relationships with multi-facility senior living and skilled nursing organizations, manage complex multi-stakeholder buying committees, forecast long sales cycles, and close six- and seven-figure deals. Partner with growth, product, and customer experience teams to transition founder-led accounts into a repeatable enterprise sales process and establish the company’s enterprise sales playbook.