Top Tech Jobs & Startup Jobs in Chicago, IL

Leads the Client Accounting division as a business unit, owning P&L, staffing, KPIs, profitability, client relationships, and service quality. Oversees inventory and cost accounting, GAAP reporting, ERP implementations, and proactive advisory for startup clients. Manages, coaches, and hires team members; handles performance, capacity, and client escalations. Drives business development, cross-functional collaboration, technology adoption, and AI-enabled efficiency.

Executes project-based accounting engagements, including historical cleanups, reconciliations, new-client implementations, chart of accounts setup, and opening balances. Manages scope, timelines, budgets, client communication, and handoffs to production teams. Supports process improvement and implementation of new accounting tools and workflows, including responsible use of AI. Requires strong accounting judgment, project management, documentation, and experience with U.S. GAAP, month-end close, and accrual-basis financial statements.

Manage multi-jurisdictional indirect tax compliance for clients, including sales, use, excise, GST/HST, OSS, and VAT filings. Conduct nexus studies, prepare voluntary disclosure agreements, research tax issues, support planning and controversy matters, maintain tax records, onboard clients, answer technical questions, and improve processes through analytics, technology integration, and AI tools.

Manage inbound sales opportunities from VC-backed startup founders and executives, guiding prospects through discovery, service recommendations, proposal, and close. Build relationships with prospects, clients, and VC referral partners; collaborate with finance, tax, and HR specialists to scope and transition engagements. Maintain CRM accuracy, monitor pipeline forecasts, research market trends, and represent the company at startup events.

Provides strategic finance leadership to venture-backed AI and SaaS startups. Responsibilities include monthly close oversight, budgeting and forecasting, capital planning, treasury management, board reporting, investor updates, fundraising, M&A support, cap table analysis, revenue cycle management, cash flow planning, controls, audit readiness, and advising founders on financial strategy.

Serve as a long-term financial advisor to healthcare clients operating under MSO/PC structures. Own monthly close, budgeting, forecasting, intercompany settlements, management fee strategy, cash flow, controls, KPI reporting, fundraising, M&A modeling, and board finance presentations. Advise CEOs, physician leaders, and investors while ensuring compliance and practice-level economic clarity. The role also identifies opportunities for bookkeeping, tax, and HR services.

Hands-on Controller for venture-backed startups: implement accounting processes and systems, manage monthly and annual closes, oversee accountants, prepare financial statements and consolidations, handle equity and convertible note reconciliations, apply ASC 606/ASC 842, and support financial due diligence for Seed through Series C clients.