Top Tech Jobs & Startup Jobs in Chicago, IL

Leads recruiting, onboarding, training, coaching, and performance management for an independent health insurance agent network. Recruits and appoints agents, conducts training and coaching, tracks production in Zoho CRM, resolves sales and compliance issues, manages performance targets, and personally sells Medicare and ACA policies during peak enrollment periods. The role is fully remote, player-coach oriented, and offers a path to Sales Director.

Oversee the full-cycle accounts payable function across multiple entities, including invoice processing, vendor maintenance, payment runs, reconciliations, tax compliance, and 1099 filings. Lead workflow improvements, KPI analytics, cash-flow reporting, and forecasting. Supervise, mentor, and develop accounts payable staff while collaborating with accounting leadership and subsidiary teams to maintain accurate, efficient financial operations.

Manage and service commercial P&C insurance accounts, prepare submissions and proposals, process changes/audits/bindings/cancellations, invoice and collect premiums, coordinate with producers, maintain accurate documentation and reports, and support growth and special projects while ensuring carrier compliance and timely client response.

Support Account Executive in delivering employee benefits programs for large group clients: manage client relationships, ensure ERISA compliance, resolve complex benefit inquiries, maintain records and benefit materials, liaise with carriers/vendors, and use agency and benefits administration systems to deliver timely, accurate service.

Manage and grow client insurance accounts by preparing submissions, obtaining quotes, negotiating coverage, servicing renewals, handling audits, invoicing, and coordinating with carriers. Maintain accurate documentation in AMS360 or Epic, ensure regulatory compliance, support collections and claims communication, implement marketing strategies for renewals, and delegate administrative tasks as needed to meet performance and service expectations.

Develop new business and service existing marine industry accounts (marinas, shipyards, yacht clubs). Assess risks and place marine liability, property, hull & machinery, P&I, and workers' compensation. Collaborate with underwriters, maintain a sales pipeline, meet revenue goals, and provide ongoing account management while tracking industry and regulatory changes.

Lead the company's legal function as senior legal advisor to CEO and Board. Oversee governance, M&A, contracts, compliance, litigation, employment matters, data privacy/security, and manage internal and outside counsel while building and directing the Legal Department to support business growth and risk mitigation.