Top Tech Jobs & Startup Jobs in Chicago, IL

Lead client-facing AI transformation and enablement engagements for mid-market companies. Design and deliver practical sessions that drive executive confidence, behavior change, and measurable AI adoption. Own client relationships between sessions, provide follow-up support and strategic guidance, stay current on AI tools, and identify adoption patterns that improve the company’s methodology. The role is full-time and remote, with travel to client sites required for some engagements.

Individual contributor responsible for hunting, developing, and closing enterprise software deals. Build executive relationships, create target account plans, generate pipeline, manage long sales cycles, coordinate delivery and billing, and maintain CRM. Meet/exceed revenue targets through strategic prospecting and in-person meetings.

Lead HR business partnership for a portfolio of hotels, advising leaders on employee relations, performance management, compliance, workforce planning, talent development, and change management. Conduct investigations, coach leaders, support shared services interactions, monitor HR metrics, and drive engagement, retention, and consistent HR practices across multi-site operations.

Processes commercial insurance policy lifecycle transactions in Applied EPIC, including new business, renewals, endorsements, audits, cancellations, reinstatements, certificates, carrier documents, and billing. Maintains accurate policy records, reviews documents and invoices, issues insurance certificates and identification cards, tracks production, meets service-level agreements, and achieves volume and quality targets in a high-volume environment.

Lead and grow Risk Control for commercial accounts by developing regional and national business plans, recruiting and managing Field Directors, collaborating with business partners, and leveraging data to improve profitability, staffing, and technical leadership. Represent the company externally and lead division projects and initiatives.

Serve as primary day-to-day contact for a book of clients, lead renewals and remarketing, onboard new accounts, troubleshoot complex issues with carriers, manage endorsements/claims/audits, maintain records in AMS360, mentor junior staff, and stay current on industry and regulatory changes.

Support Business Development Managers by managing assigned accounts, nurturing relationships, qualifying leads, participating in discovery and scoping, coordinating internal teams, tracking CRM activity, identifying expansion opportunities, and periodically traveling within the territory to grow services revenue.

Support testifying experts on antitrust and related litigation by designing and implementing econometric and statistical analyses, cleaning and analyzing data, managing workstreams, mentoring junior staff, producing written reports and exhibits, and communicating complex economic concepts to attorneys and clients.

Serve as a senior appraisal consultant for multifamily properties: provide valuation subject-matter expertise, review and order appraisals, advise internal stakeholders, support vendor oversight, update appraisal standards, participate in technology and process improvements, conduct training, and analyze property-related valuation risk to support Freddie Mac multifamily lending.

Lead engineering delivery for Microsoft Dynamics 365 Finance & Supply Chain Management: approve technical designs, enforce code-review standards, oversee X++ development, integrations, SSRS and Electronic Reporting, mentor and hire engineers, manage production support, backlog and release planning, and drive engineering quality, scalability, and continuous improvement.