Top Tech Jobs & Startup Jobs in Chicago, IL

Build integrations that enable AI agents to interact with first-party and third-party applications. Develop structured agent actions, information retrieval interfaces, cross-application workflows, reusable SDKs, and reliable asynchronous APIs. Manage authentication, authorization, permissions, and integration limitations while collaborating with Android engineers on system-level application access.

Build and scale AI agents for sales enablement across frontend and backend systems. Lead development with Next.js, React, TypeScript, Python, Postgres, OpenAI, and FastAPI; design robust AI integrations, engage customers, contribute to roadmap planning, and iterate rapidly in a high-ownership startup environment.

Provides first-line technical support to internal users and external clients through phone, email, and chat. Diagnoses and resolves hardware, software, operating system, application, networking, printer, and peripheral issues; installs and maintains systems; documents tickets; escalates complex problems; trains users; supports updates and maintenance; and tracks requests against SLAs.

Serve as a trusted technical advisor for 12–15 strategic enterprise accounts. Design, implement, configure, and optimize ControlUp solutions; drive adoption, automation, AI capabilities, renewals, and expansions. Provide workshops, technical guidance, troubleshooting, best practices, and customer advocacy. Partner with Customer Success, Sales, and Presales while developing technical collateral and contributing to internal product and process improvements.

Build and deploy machine learning models for risk and fraud detection. Lead technical efforts in the risk and fraud domain, use SQL and Python for data preparation and production code, design statistically sound experiments, evaluate model performance, and partner with Operations to respond to evolving financial threats.

Own the full sales cycle for small school and district accounts, including prospecting, qualification, discovery, demonstrations, proposals, negotiation, closing, renewals, and expansion. Build relationships with K-12 decision-makers, manage a high-volume pipeline, meet sales quotas, maintain accurate CRM forecasts, provide market insights, and represent Kami at education conferences. This is a remote role with travel of up to 25%.

Manage and grow strategic enterprise accounts through consultative upselling, cross-selling, renewals, and complex expansion sales. Build executive relationships, lead multi-stakeholder sales cycles, conduct presentations and demonstrations, maintain CRM pipeline forecasts, and meet revenue targets. Collaborate with client engagement, product, marketing, and revenue operations teams while identifying account risks and opportunities. Mentor junior team members and improve sales processes.

Administers and supports SIM International’s technology systems, including Microsoft ecosystem applications. Monitors system reliability, security, and user experience; resolves or escalates support requests; maintains IT processes and controls; coordinates with vendors; develops recommendations and user-friendly SharePoint content; and provides end-user training across time zones.

Drive enterprise SaaS sales from prospecting through close, expanding adoption among strategic accounts. Engage business and technical decision-makers, including C-suite stakeholders, to address fraud challenges using Sift’s machine learning platform. Build consultative business cases, articulate platform differentiation, collaborate cross-functionally, and help shape sales strategy and growth. Requires strong organizational skills, adaptability, and experience managing complex B2B sales cycles.

Build and scale backend infrastructure for AI-driven freight finance workflows, including document processing, APIs, data pipelines, audit engines, integrations, observability, and performance monitoring. Collaborate with AI/ML teams to productionize model outputs, integrate freight and financial systems, improve engineering practices, and make frontend updates as needed in a remote-first startup environment.