Top Tech Jobs & Startup Jobs in Chicago, IL

Leads enterprise application portfolio assessments, migration strategies, modernization roadmaps, and target-state cloud architecture, primarily on AWS with Azure and GCP awareness. Develops application treatment decisions, migration sequencing, risk registers, business cases, effort estimates, and DevSecOps transformation designs. Supports proposal solutioning, client workshops, technical defenses, platform development, GenAI-assisted assessment tooling, proofs of concept, and executive presentations across complex, heterogeneous application environments.

Design the user experience for Sayge’s ecosystem, working across complex enterprise tooling and consumer-facing applications.

Own the architecture and implementation of a regulated bank’s transactional core, including ledger, stablecoin issuance, reconciliation, event messaging, APIs, and microservices. Lead backend engineers, establish engineering standards, integrate sanctions screening, and ensure resilience, observability, auditability, and regulatory readiness. Partner with SRE and Security teams on multi-region availability, IAM, key management, and threat modeling while supporting UAT and external control validation.

Supports cybersecurity pre-sales engineering through customer demos and proof-of-concept engagements. Assists product marketing with technical datasheets, white papers, blogs, videos, and collateral. Researches compliance standards, security frameworks, emerging threats, and attack vectors. Participates in product testing as the voice of the customer. The role is remote and includes training in cloud platforms, Kubernetes, security tools, programming, and security research.

Staff Accountant responsible for financial accounting, payroll, project accounting, invoicing, accounts receivable, reconciliations, cost accounting, fixed assets, month-end close, reporting, audit support, and internal controls. The role partners with US and Australian finance teams and cross-functional departments while supporting process improvements and adherence to global accounting policies.

Sets technical direction for Helix’s Experience platform and broader engineering organization. Designs and implements distributed, full-stack genomic software systems focused on patient and provider experiences. Leads complex projects from scoping through production, advances AI-assisted engineering practices, establishes quality and delivery standards, mentors technical leaders, and drives cross-functional collaboration with product, design, research, scientific, and business teams.

Lead client engagements on benefits strategy, plan design, open enrollment, and administration. Stabilize operations, manage carriers/brokers, execute transitions and platform migrations, ensure compliance, advise on cost optimization and multi-state/global expansion, and expand client relationships.

Own and scale multi-channel growth programs for Oscilar’s AI Agents product, generating and accelerating qualified enterprise pipeline. Develop campaigns across outbound, inbound, ABM, events, webinars, paid, and direct mail; partner with Sales, BDRs, Product Marketing, and Events; run rapid experiments; analyze funnel performance; leverage GTM automation, AI tools, and intent signals; and turn market feedback into messaging, targeting, and repeatable playbooks.

Build and deploy domain-specific AI agents and AI-native workflow systems for operating companies. Responsibilities include developing evaluation infrastructure, fine-tuning and routing frontier and open models, migrating legacy datasets, observing customer workflows, creating reusable AI engineering infrastructure and playbooks, and managing embedded AI engineers while spending approximately 90% of the time building.

Serve as the primary support contact for partner veterinary practices: respond to inbound requests via email/phone/chat, troubleshoot billing and platform issues, maintain support records, create self-serve content, escalate bugs to Product, and collaborate cross-functionally to improve the client experience.