Top Tech Jobs & Startup Jobs in Chicago, IL

Lead global DevOps, SRE, and platform engineering to improve reliability, scalability, and delivery velocity. Drive CI/CD (Harness), observability (Dynatrace), incident management, and AI Operations (AIOps, Temporal, LangChain). Recruit and scale onshore/offshore teams, manage vendors and budgets, implement IaC and Kubernetes/cloud-native practices, and champion continuous improvement and SRE maturity across large-scale digital platforms.

Investigate and resolve customer production issues by analyzing SQL, data feeds (HL7/CSV), and Python code. Communicate status and root cause to customers, collaborate with Data Engineering and Product teams, document tickets in Jira, validate fixes with queries, and contribute to knowledge base and troubleshooting playbooks.

Support and maintain production Core Speech systems: deploy, monitor, alert, perform capacity planning, respond to on-call incidents, and drive system performance and architecture improvements.

Own customer success for assigned cloud accounts to drive retention and expansion. Build strong customer relationships, run success and business reviews, manage renewals and escalations, monitor account health, create dashboards and success plans, identify expansion opportunities, and improve adoption and NPS.

Design, optimize, and operate production LLM inference and training pipelines. Improve latency, throughput, and GPU utilization using techniques like batching, quantization, FlashAttention, and kernel-level profiling. Deploy and autoscale multiple models on shared GKE GPU clusters, consult with clients on performance and cost requirements, and carry prototypes to robust, scalable production services.

Lead growth product strategy for user acquisition, onboarding activation, and trial-to-paid conversion. Design and run high-velocity A/B and multivariate experiments, prioritize initiatives by ROI, and collaborate with UX, engineering, marketing, and data teams to optimize funnels and monetization. Build dashboards, partner with analytics/data science to find conversion bottlenecks, and drive measurable revenue and retention outcomes.

Serve as in-house senior counsel providing commercial and corporate legal support focused on drafting and negotiating partnership and go-to-market agreements. Advise on regulatory compliance, data privacy, securities/SEC reporting, trade secrets, advertising law, and technology-specific legal issues. Manage litigation or coordinate outside counsel and support corporate transactions and contract management.

Support, maintain, and administer IBM z/OS mainframe environments with emphasis on CICS and IBM MQ. Perform installations, upgrades, troubleshooting, performance tuning, security compliance, disaster recovery, change and incident management, documentation, and mentor junior staff.

Build and own end-to-end full-stack systems using AI-assisted development. Identify opportunities for automation and product impact, design and implement backend services, internal tools, and experiments, work with cloud and edge platforms, maintain reliability and observability, conduct code reviews, mentor engineers, and iterate on solutions with stakeholders to measure business outcomes.

Lead strategy and operating model for bookkeeping, payroll, and tax services. Drive automation and AI adoption, establish scalable workflows and KPIs, grow and mentor a 25+ person team, and partner cross-functionally to align product, fintech, and go-to-market for seamless, compliant financial service delivery.

The Account Executive is responsible for onboarding service professionals to Housecall Pro, providing tailored solutions, delivering product demos, and ensuring great customer service throughout the sales process.

The Vertical Vice President, Technology drives engineering execution, operational excellence, and organizational capability across the Wedding & Events Vertical. Responsibilities include overseeing engineering teams, improving platform reliability, and implementing AI-enabled practices for enhanced productivity and product innovation.