Top Tech Jobs & Startup Jobs in Chicago, IL

Leads platform engineering strategy across Azure infrastructure, legacy Windows Server workloads, infrastructure as code, CI/CD, reliability, identity, security, cost optimization, and engineering tooling. Builds and develops a platform engineering team while overseeing tenant consolidation, modernization, observability, incident response, and developer self-service. Partners with Security and Compliance to support sensitive and regulated data environments.

Leads sales operations, coaches representatives and managers, manages KPIs and CRM processes, oversees training and hiring, supports financing and transactions, and drives accountability, productivity, and revenue growth across sales teams.

Design, build, and productionize LLM-powered systems (adaptive content, tutors, evaluators) and AI pipelines (RAG, embeddings, fine-tuning). Prototype and optimize models across modalities, define AI safety/evaluation/observability practices, and collaborate with product and engineering to measure learner outcomes and iterate.

Design, develop, and deliver in-person and virtual training for software end users. Create training materials, customize curricula, support users, gather feedback, and collaborate with internal teams on product updates. Facilitate client testing and validation of converted data, business processes, and software modifications. The role also requires troubleshooting, instructional design, strong communication, and knowledge of cloud concepts.

Manage complex SaaS implementations and enterprise district portfolios, driving engagement, usage, outcomes, renewals, and expansion. Build executive relationships, assess account health, facilitate renewals, provide structured product feedback, document customer challenges, and maintain CRM records. The role requires strong project management, interpersonal, technical, and remote-work skills, with 15–30% travel to customer meetings, trainings, conferences, and company events.

Own a portfolio of automotive dealership accounts from onboarding through long-term success. Lead onsite platform launches and training, conduct follow-up sessions and strategic reviews, drive product adoption and customer retention, identify expansion opportunities, monitor engagement, maintain client relationships, and relay customer feedback to internal teams. The remote role requires nationwide travel of up to 50%.

Executive leader responsible for Study Smart’s revenue strategy, go-to-market functions, sales growth, partnerships, forecasting, pricing, and organizational performance. The role oversees marketing, business development, renewals, and RFP efforts; develops revenue plans and dashboards; coaches senior leaders; identifies expansion opportunities; and represents the organization with strategic partners and education stakeholders. This hybrid position reports to the Chief Strategy Officer and requires national travel as needed.

Reviews and analyzes conflicts reports for new clients, matters, and lateral hires. Advises partners on legal and business risks, drafts conflict waivers, prepares ethical walls, audits intake data, researches professional conduct rules, and resolves conflicts. Guides conflict analysts, monitors ethics developments, communicates potential issues, and participates in urgent and on-call support.

The Accounting Manager oversees monthly, quarterly, and annual close processes, general ledger activities, reconciliations, consolidated financial reporting, internal controls, audits, compliance, payroll accounting, cash management, and process improvements. The role ensures U.S. GAAP compliance, supports systems and automation initiatives, partners across departments, analyzes financial results, and mentors accounting team members.

Generate and close small-account sales through cold outreach, prospecting, presentations, negotiations, and pipeline management. Develop digital advertising proposals, maintain CRM records, organize sales collateral, support sales-team operations, and provide account coverage during staff absences. Collaborate with creative, advertising operations, production, and editorial teams while managing client relationships remotely.