Top Tech Jobs & Startup Jobs in Chicago, IL

Manage and expand enterprise accounts by driving renewals, upsells, and strategic negotiations. Serve as trusted advisor to executives, design tailored account strategies, lead cross-functional initiatives, and mentor peers to maximize customer value and retention.

Lead origination of private credit loans for lower middle-market companies. Source opportunities via borrower outreach and intermediaries, structure financing, prepare and negotiate term sheets, maintain a high-volume pipeline and forecasting, and collaborate with underwriting and portfolio teams to close transactions and build long-term referral relationships.

Lead development of internal Python SDKs and agentic AI workflows, build scalable FastAPI ML services, maintain CI/CD with Jenkins/GitLab Runners, and use Galileo for model evaluation and observability to productionize autonomous systems.

Lead architecture and hands-on implementation of large-scale Generative AI and agentic systems. Build production-ready RAG, embedding fine-tuning, vector search, and MLOps pipelines on Google Cloud. Advise clients in pre-sales, mentor engineers, and ensure reliability, latency, cost, and responsible-AI controls for high-stakes deployments.

Own and drive Cents OS product across in-store attendant tools (Cents POS) and operator-facing controls (Cents Business Manager). Define strategy, run discovery, write requirements, lead agile delivery with distributed engineering and design teams, track metrics, and execute launches. Engage stakeholders, conduct user research, and continuously improve processes to deliver reliable, scalable solutions that help laundromat and garment care operators run their businesses.

Own strategy, roadmap, and governance for external APIs used by partners and enterprise customers. Define API design standards, auth, versioning, rate limiting, SLAs, and developer experience (docs, sandbox, webhooks). Partner with Partnerships, Sales, and engineering to drive integrations, go-to-market, and measure ecosystem success via adoption and reliability metrics.

Lead QA automation efforts by designing, building, and maintaining automated test frameworks and suites, leveraging Agentic AI to generate and optimize tests, executing manual and automated regression/integration tests, collaborating with engineering on testability, reporting defects, and driving QA best practices and mentoring within the team.

Deliver end-to-end software implementations for fleet/asset management clients: gather requirements, configure web applications, create functional/technical specs, manage UAT, deliver train-the-trainer and end-user training, support go-live troubleshooting, build reports, and liaise with development, QA, and customer care.

Provide 24/7 technical support to clinicians and administrators via phone, chat, and portal. Assist with user account management, training, on-call schedule management, mobile/web troubleshooting, application configuration, and escalate complex issues to cross-functional teams.

Lead end-to-end B2B integrated marketing to drive pipeline and revenue. Build and execute multi-channel demand generation (paid, email, social, webinars, events), optimize digital campaigns and website, create content for broker/HR education, align with sales/rev ops, and scale marketing automation and AI-driven processes.

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.