Director of Finance And Accounting

Our Chicago based Cannabis Client is seeking a hands-on , experienced Director of Finance to lead the day-to-day finance and accounting function for a complex, multi-entity cannabis organization. This is a great opportunity for someone to break into the rapidly growing cannabis industry with a reputable company known for positive culture and quality product. The ideal candidate will have start-up experience and likes getting into the weeds (no pun intended)!

The Director will oversee accounting operations, financial reporting, cash management, budgeting and forecasting, payroll and benefits accounting, tax-process coordination, and the development of reliable financial controls and procedures.

This role is designed for an operational finance leader. The Director will be responsible for the accuracy, timeliness, and usefulness of the company’s financial information and will translate that information into practical insights for senior leadership and operating teams. The Director will work closely with external accounting, tax, banking, and other professional advisors, while remaining accountable for internal execution and follow-through.

Key Responsibilities

Finance Team Leadership and Accounting Operations

● Lead, coach, and develop the finance and accounting team; establish clear

responsibilities, service standards, deadlines, and review processes.

● Oversee bookkeeping and accounting for a complex portfolio of managed legal entities, bank accounts, credit cards, retail locations, and cultivation and production operations.

● Own timely, accurate month-end and year-end close processes, including account

reconciliations, journal-entry review, accruals, and consolidation of management

reporting.

● Oversee reconciliations of bank and credit card accounts; point-of-sale activity; sales, payment methods, inventory, cost of goods sold, and cash balances at retail locations.

● Ensure accurate accounting for cultivation and production activities, including inventory, direct and indirect cost of goods sold, and production expenses.

● Maintain accurate intercompany accounting, allocations, and transfer-pricing records in coordination with external tax and accounting advisors.

● Oversee partnership accounting where applicable, including contributions, distributions, and investment income.

● Maintain effective customer and vendor records, invoicing, accounts receivable

monitoring, accounts payable processes, and year-end information reporting.

● Develop, document, and improve accounting policies, internal controls, standard

operating procedures, and record-retention practices. Cash Management and Banking

● Prepare and maintain weekly cash analyses and a rolling 13-week cash flow forecast.

● Lead the weekly accounts payable review and payment process, including

recommendations based on liquidity, due dates, and operating priorities.

● Monitor cash balances and ensure sufficient funding for payroll, benefits, taxes, debt service, and other critical obligations.

● Administer company bank accounts and day-to-day commercial banking relationships, including compliance requests and account maintenance.

● Coordinate approved cash movements, intercompany transfers, and distributions in accordance with established authorization controls.

● Monitor cash transportation services, retail deposit activity, and electronic payment providers; investigate and resolve discrepancies promptly.

Financial Planning, Analysis & Reporting

● Produce timely monthly financial statements, management reports, and reporting

dashboards for senior leadership and operating teams.

● Lead the annual budgeting process and maintain forecasts that reflect current operating performance, cash needs, and business priorities.

● Analyze revenue, gross margin, operating expenses, labor, inventory, working capital, and location- or entity-level performance; identify trends, risks, and opportunities.

● Partner with operational leaders to explain results, improve financial discipline, and support data-informed decisions.

● Prepare financial schedules and calculations required for contractual or preferred

distributions.

● Provide accurate financial information for routine diligence and business needs,

including insurance, employee benefits, banking, financing, licensing, and vendor

requests.

Payroll and Benefits Financial Oversight

● Provide leadership and oversight to the payroll and benefits finance function, in close partnership with Human Resources.

● Ensure adequate cash is available for timely payroll, benefit contributions, retirement- plan contributions, workers’ compensation payments, and other employee-related obligations.

● Oversee payroll and benefits reconciliations, accounting entries, deductions, funding, and related audits.

● Maintain appropriate controls over payroll changes, approvals, reconciliations, and issue resolution.

Tax, Audit and External Advisor Coordination

● Oversee the timely preparation and filing process for sales, cannabis, privilege, payroll, and other recurring taxes, using external advisors where appropriate.

● Coordinate with external tax accountants by providing complete and accurate financial information, responding to accounting questions, and project-managing filing calendars and deadlines.

● Support external reviews, audits, tax examinations, and other financial diligence by organizing records, preparing schedules, and coordinating responses.

● Manage the internal preparation and documentation needed for external accounting firms to complete reviewed or audited financial statements.

● Escalate technical tax positions, complex accounting judgments, capital-structure

matters, and other specialized issues to the CEO and appropriate external advisors.

Systems, Controls & Continuous Improvement

● Evaluate and improve accounting systems, reporting tools, workflows, and integrations across point-of-sale, inventory, banking, payroll, and general-ledger platforms.

● Strengthen controls appropriate for a cash-intensive, highly regulated, multi-entity

business.

● Establish clear financial calendars, ownership, review checkpoints, and documentation standards.

● Identify opportunities to improve efficiency, accuracy, visibility, and scalability without compromising compliance or control.

Qualifications

● Bachelor’s degree in accounting, finance, business administration, or a related field required.

● At least 8 years of progressive accounting and finance experience, including at least 3 years leading an accounting or finance team.

● Demonstrated experience owning the finance function or serving as a senior finance leader within a similarly sized, multi-site, multi-entity operating company.

● Strong command of U.S. GAAP, month-end close, financial reporting, cash forecasting, budgeting, internal controls, and operational accounting.

● Experience supporting inventory-based retail, manufacturing, cultivation, consumer products, or another business with complex cost accounting strongly preferred.

● Experience in a highly regulated industry—such as cannabis, healthcare,

pharmaceuticals, alcohol, gaming, or financial services—strongly preferred; direct

cannabis industry experience is a plus but not required.

● Proven ability to manage competing deadlines, improve processes, and maintain

accuracy across complex organizations.

● Strong analytical skills and the ability to communicate financial information clearly to both finance and non-finance audiences.

● High integrity, sound judgment, discretion, and a practical, solutions-oriented approach.

● Advanced proficiency with accounting systems and spreadsheets; experience integrating data across operational systems is strongly preferred.

● CPA or CMA designation preferred but not required.

● Must be at least 21 years of age and able to satisfy any background-check or agent- credential requirements applicable to the role.

Leadership Profile

● Hands-on leader who is comfortable moving between detailed accounting review and broader operational analysis.

● Builds accountable, service-oriented teams and develops staff through clear

expectations, coaching, and feedback.

● Works effectively in an entrepreneurial environment where systems are still evolving and priorities can change quickly.

● Balances urgency with disciplined controls and knows when to engage external

specialists or escalate decisions.

● Collaborates well with operations, human resources, compliance, legal, and senior

• leadership.