Top Tech Jobs & Startup Jobs in Chicago, IL

Lead and scale an Enterprise Customer Success team (6-8 CSMs) to drive adoption, retention, and expansion for SaaS enterprise customers. Define strategy, build technical depth, mitigate risk using data, partner cross-functionally, manage executive escalations, hire and develop talent, champion AI workflows, and improve customer outcomes and renewals.

Full-cycle contract recruiter supporting GTM teams (Sales, Customer Success, Sales Ops, Enablement, Renewals). Source and engage passive candidates, manage requisitions and candidate experience, advise hiring managers, run interview debriefs and offer negotiations, use data to inform searches, maintain ATS records, and drive diverse hiring and inclusive interviewing practices.

Lead the architecture and technical vision for AI-powered GTM systems, defining patterns for low-code and custom agentic pipelines. Build reference architectures, design multi-system integrations and RAG/LLM orchestration, evaluate AI tools, drive governance and observability, and partner with GTM leadership to deliver production-grade, scalable solutions.

Lead analytics and reporting for post-sales segments, reconcile data across Salesforce and financial/CS systems, design and enforce renewals and customer success processes, build adoption and retention reporting, and translate insights into recommendations for leadership to improve renewal rates and revenue retention.

Serve as the technical authority for ELD compliance product escalations, analyze device telemetry and fleet patterns, coordinate fixes with R&D via Jira, support audits/inspections, lead post-mortems and runbook/validation creation, build internal tools, and coach support engineers to improve resolution speed and product reliability.

The Staff ML Engineer will design and operate Samsara's ML platform, collaborating with teams to enhance ML features and improve safety outcomes. Responsibilities include overseeing system reliability, leading technical direction, and mentoring engineers.

The Specialist Seller will lead go-to-market strategies for AI products, partnering with sales teams to drive high-value enterprise sales, architect complex deals, and develop product pipelines while building relationships with major accounts.

The role involves building core infrastructure for orchestrating intelligent agents, defining platform primitives, and ensuring systems scale and reliability. Collaboration with internal teams and end-to-end system ownership are essential.

The Sales Operations Manager will optimize processes, lead cross-functional programs, and improve sales efficiency to drive revenue growth for Samsara's Enterprise Sales organization.

Provide end-to-end commercial litigation support, advise on subpoenas and customer data privacy, manage eDiscovery lifecycle with automation/AI, mitigate and resolve disputes, drive process and technology-enabled innovation, and deliver actionable legal insights to cross-functional stakeholders.