Top Tech Jobs & Startup Jobs in Chicago, IL

Lead accounting and financial reporting for CIRI and affiliates. Oversee consolidated financial statements, internal controls, shared services, audits, acquisitions integration, GAAP compliance, regulatory reporting, budgeting support, system implementations, and supervise and develop the accounting team.

Lead and manage the engineering team to design, build, deploy, and maintain cloud-based social media/influencer marketing and AI platforms. Oversee software architecture, large-scale data pipelines, image/video processing, and AI/ML solutions. Coordinate cross-functional work, hiring, project planning, Agile delivery, and continuous system improvement.

Lead technology strategy, cybersecurity, infrastructure, compliance (HIPAA, NIST, SOC 2, HITRUST, FedRAMP), product security, cloud operations, vendor management, incident response, and AI governance. Oversee reliability, disaster recovery, secure development practices, audits, and cross-functional partnerships to support healthcare and public-sector customers.

Provide technical, customer-facing implementation and support for Watershed. Build and maintain data pipelines and API integrations, create reports and dashboards, consult on best practices, automate deployment workflows (CI/CD), troubleshoot issues, train clients, and occasionally contribute to core product updates to help clients act on learning data.

Lead research, design, and production implementation of computer vision and ML solutions. Define architectures, run experiments, own model lifecycle (data, training, evaluation, deployment), optimize inference, set MLOps standards, mentor engineers, and collaborate with product and engineering teams to deliver production-quality CV features.

Lead reporting and analysis across product, call center, and marketing; manage enrollment and revenue reconciliation; produce partner and carrier reports; analyze member engagement and plan performance to surface actionable insights.

Conduct outbound outreach across channels, qualify leads, conduct discovery calls, update CRM (Salesforce/Hubspot/Gong), partner with marketing and Account Executives, manage territory accounts, and pursue quota with uncapped commission in a remote East Coast role.

Design, develop, test, and maintain cloud-native, scalable search and distributed system features. Contribute to architecture, ensure reliability, scalability, and security of global cloud infrastructure. Troubleshoot production issues, optimize performance, collaborate with product and UX, and mentor junior engineers.

Own and evolve ShiftKey's AI infrastructure: production retrieval/indexing, agentic platforms on AWS, graph-based multi-hop retrieval design, platform APIs, reference agents, and cost/observability guardrails for regulated (HIPAA) workflows.

Own and execute the group-wide payments strategy across a family of Bitcoin-native businesses. Define and operate ElenPay (PSP), expand PSP growth, integrate payments with the banking house, productize Bitcoin-native infrastructure (liquidity, routing, swaps, LSP services), and capture frontier rails (stablecoins, cross-border, machine-to-machine). Deliver roadmaps, commercialization, merchant funnels into banking services, and live liquidity/swap products in-market.