Top Tech Jobs & Startup Jobs in Chicago, IL

Manages full-cycle accounting services for multiple clients, serving as the primary liaison and reviewing financial deliverables for accuracy. Responsibilities include preparing journal entries, reconciling general ledger accounts, budgeting and variance tracking, producing financial reports, coordinating client financial review meetings, presenting results, and mentoring staff accountants.

Directs the workers’ compensation underwriting function for a large deductible insurance program, overseeing risk assessment, pricing, regulatory compliance, client performance, and profitability. Leads underwriting process design, establishes guidelines and quality standards, manages escalated prospects, and partners with Sales and Risk leadership. Recruits, mentors, and evaluates underwriting staff while administering safety incentives and supporting strategic program growth.

Drives B2B sales revenue for professional employment services, identifies opportunities within assigned accounts, develops proposals and pricing estimates, manages negotiations and client communications, tracks proposal progress, coordinates cross-functional project plans, supports marketing and product initiatives, and maintains ongoing client relationships. The role requires at least three years of professional services sales experience serving small and midsize businesses.

Configure, maintain, troubleshoot, and support the isolved HCM platform, including Time & Attendance. Manage implementations, testing, integrations, releases, outages, client requests, vendor relationships, and project deliverables. Train clients and internal users, document procedures, prioritize support issues, and recommend process improvements. The role also provides consultative client configuration, technical planning, reporting coordination, and ongoing system support while ensuring compliance with labor laws and organizational needs.

The Senior Onboarding Accountant leads new-client accounting implementations, including system conversions, bookkeeping cleanup, reconciliations, month-end close, chart-of-accounts alignment, reporting, budgeting, audit support, and process documentation. The role presents financial insights to clients, implements third-party applications, trains stakeholders, mentors onboarding associates, manages project risks, and uses Excel, VBA, macros, and AI tools to automate workflows and improve accuracy.