Top Tech Jobs & Startup Jobs in Chicago, IL

Serve as a strategic operator and close partner to the President: translate strategy into priorities and OKRs, run annual/quarterly planning and operating rhythm, govern portfolio and dashboards, lead cross-functional initiatives, apply AI/automation/analytics to improve operations, and support growth, M&A, and integration to ensure measurable execution.

Design, build, and maintain scalable test automation frameworks and tooling (Playwright, C#, JS/TS). Integrate automated tests into CI/CD, develop end-to-end, integration, and performance tests, apply AI techniques for test generation and defect detection, troubleshoot system issues, mentor QA teams, and drive automation and quality engineering best practices.

Perform tax form and regulation research, interpret tax code updates, guide programmers on calculation changes, design and execute tests, document calculations, contribute release notes and customer guidance, and support tax software products remotely.

Prepare federal and state S‑Corp and C‑Corp tax returns and supporting workpapers; calculate entity-level state tax accruals, estimated and extension payments, and assist K-1 processing. Research tax issues and new legislation, respond to state notices and audits, collaborate with Treasury/Accounting/Legal/International tax teams, support shareholder tax relations, and help implement process improvements and automation.

Lead enterprise and hybrid cloud architecture strategy and governance. Define reference architectures, hybrid cloud roadmaps, and guardrails. Guide Nutanix private cloud integration, evaluate Azure/AWS/GCP services, enable self-service platforms, mentor architects and engineers, and support executive decision-making to deliver secure, resilient, and scalable platform solutions.

Manage corporate compliance and transactional needs for multinational entity portfolios. Serve as primary client contact, coordinate with internal fulfillment teams via Salesforce CRM, research jurisdictional filing requirements, oversee annual compliance and ad hoc transactions, provide status updates, mentor junior staff, and maintain accurate company records in entity management systems.

Process agent resignations, handle and review physical mail, create and print checks, prepare certified USPS notifications, manage internal inboxes and state websites, use Company Records, Order Fulfillment, Salesforce and Outlook, support automated processes, cross-train on compliance-related functions, and prioritize accuracy and deadlines in a high-volume environment.

Manage and build long-term client relationships for Corptax customers, respond to inbound support across channels, drive product adoption, document and triage issues, perform release testing, and collaborate on support projects while maintaining high customer satisfaction.

Provide B2B client support by answering inquiries via phone and electronic channels, managing workflows, navigating multiple databases, resolving problems, recommending process improvements, and maintaining/growing client relationships. Work Monday–Friday on Hawaii time with required training hours.

Lead second-line IT risk oversight for technology, cyber, data and AI. Perform risk assessments, advise on controls and product launches, drive policy and remediation, support regulatory compliance, and report to executives and board on information security themes.