Top Tech Jobs & Startup Jobs in Chicago, IL

Own reliability and security of CI/CD and production services: define SLI/SLOs, lead incident response and postmortems, build observability (Datadog), operate Kubernetes and IaC (Terraform), harden pipelines with SAST/DAST/SCA and policy-as-code, and coach teams on reliability and operational best practices.

Lead post-contract partner management for strategic collaborations: own onboarding, cross-functional execution, performance tracking, renewals, and expansion. Negotiate agreements, run business reviews, surface insights to product and GTM teams, and drive measurable partner growth and retention.

Lead the MyFitnessPal Federal business unit overseeing security, compliance, P&L, delivery, and the relationship with a DoD prime. Stand up and govern a federal-facing team, translate government requirements into product and delivery roadmaps, manage contractual and data-handling obligations (CUI/PII), and serve as the senior liaison to prime and government stakeholders.

Lead a cross-functional backend and iOS engineering squad to grow paid subscribers by building and maintaining app store and Stripe integrations, prioritize platform stability, drive growth experiments, manage delivery and tech debt, and coach engineers through close partnership with Product and Design.

Lead strategy, roadmap, and measurable outcomes for Cal AI, an early-stage mobile app. Own product direction, drive cross-functional alignment, champion continuous discovery and experimentation, scale the product post-product-market fit, and improve MyFitnessPals product operating model to deliver durable user and business growth.