Top Tech Jobs & Startup Jobs in Chicago, IL

Own the roadmap and execution for core pricing, risk, and AI platform foundations across the insurance policy lifecycle. Partner with customers, brokers, underwriters, engineering, data science, actuaries, and go-to-market teams to prioritize problems, shape product direction, make technical decisions, and deliver products on aggressive timelines. The role requires quantitative strength, strong communication, cross-functional leadership, and experience working in high-growth environments.

The Cybersecurity Engineer detects and responds to threats, improves endpoint visibility and security posture, supports incident response, automates alerting and reporting, manages vulnerabilities, and partners with IT on patching and system hardening. The role monitors hybrid environments, investigates suspicious activity, documents security standards, and drives continuous improvement. It requires enterprise IT and cybersecurity experience, endpoint security expertise, scripting skills, and strong Windows Server knowledge.

Manage a portfolio of high-value real-money gaming players, building relationships and delivering personalized communications, rewards, and experiences. Drive retention, reactivation, engagement, and player lifetime value through data-informed initiatives. Resolve VIP requests and escalations professionally, collaborate with Product and Marketing, provide player insights, and ensure responsible gaming and regulatory compliance. The role is fully remote, primarily aligned with US time zones, with occasional weekend availability required.

Manages vegetation-management contractors across Illinois solar projects, including vendor identification, contract negotiations, performance tracking, KPI enforcement, safety and quality oversight, environmental compliance, O&M budget management, cost analysis, forecasting, and reporting. Coordinates grazing, mowing, herbicide, invasive-species control, and restoration activities with solar O&M teams. Builds relationships with landowners, farmers, communities, officials, and regulators while supporting ecological initiatives and mitigating vegetation-related operational risks.

Provides legal and administrative support to the General Counsel, including contract drafting and lifecycle management, corporate governance, government procurement research, compliance audits, due diligence, financing activities, and coordination with outside counsel. The role also maintains legal records, develops internal processes, and prepares executive reports. Requires substantial paralegal experience in defense, aerospace, government, or regulated technology environments and familiarity with FAR, DFARS, CUI, cybersecurity, and export control requirements.

Supports EPC partners using Palmetto’s renewable-energy financing products by managing portal queues, resolving transaction blockers, providing partner coaching, and handling support requests. The role collaborates with regional Relationship Managers, builds partner relationships, analyzes interaction trends, supports pipeline reviews, and contributes to process and product improvements that increase partner engagement and customer experience.

The Staff Accountant manages domestic and international accounting activities, including accounts payable, bank and general ledger reconciliations, fixed assets, depreciation, taxes, payroll postings, corporate card expenses, accruals, and prepaids. The role supports month-end and year-end close, flux analysis, financial reporting, dashboards, and external audits. It requires accurate, independent execution, collaboration with leadership and vendors, and proficiency in advanced Excel and Microsoft Office tools.

Leads IT engineering strategy, teams, and delivery across infrastructure, cloud, networking, compliance, and client implementations. Oversees enterprise and hybrid-cloud solutions, automation, monitoring, DevOps, security compliance, and continuous improvement. Partners with executives, service delivery, sales, account management, and clients on roadmaps, technical solutions, proposals, and business outcomes. Ensures projects meet scope, budget, quality, security, and client requirements while driving scalable MSP services.

Identify, qualify, and develop new business opportunities across the Americas. Build sales pipelines through phone outreach, email campaigns, market intelligence, and customer discovery. Manage sales qualification, support marketing activities and events, maintain CRM and sales administration records, and communicate effectively with prospective customers. The role requires ERP sales experience, particularly with SAP Business One or Microsoft Business Central, strong sales management skills, customer focus, presentation ability, and willingness to travel.

Lead end-to-end implementations of Pinewood.AI for North American dealership accounting teams, including discovery, configuration, workflow validation, training, go-live, and hypercare. Coach users on dealership financial processes, localize training materials, support change adoption, manage multi-site rollouts, and collaborate with product and delivery teams. The role requires extensive travel across the United States and Canada and involves mentoring colleagues and improving implementation methodologies.