Assistant Controller Jobs in Chicago, IL

Financial Controller - Freight/Logistics Industry Experience Required

About us

Roots Logistics is a dynamic and rapidly growing freight brokerage headquartered in downtown Chicago, with operations in Miami and Colombia.

As a modern 3PL provider, we leverage technology and industry expertise to deliver exceptional transportation solutions to our clients. We're building a high-performing organization that values innovation, integrity, and operational excellence.

About the job

We are seeking an experienced Financial Controller with specialized freight brokerage expertise to drive financial strategy and operational efficiency across our organization.

This integral role will be instrumental in optimizing our financial operations, ensuring regulatory compliance, and providing strategic insights to support our aggressive growth trajectory. The ideal candidate will combine deep financial acumen with a comprehensive understanding of freight brokerage economics, carrier/customer relationships, and industry-specific financial challenges.

KEY RESPONSIBILITIES

Financial Operations & Analysis:

• Maintain full P/L responsibility for assigned business units, ensuring accurate revenue and expense tracking
• Develop and maintain financial models for our freight brokerage operations, including margin analysis, lane profitability, and customer/carrier pricing strategies
• Analyze commission structures, load profitability, and operational metrics to identify revenue optimization opportunities
• Manage cash flow forecasting with emphasis on quick-pay programs, factoring relationships, and carrier payment terms
• Work directly with factoring companies to optimize cash flow and manage receivables financing relationships
• Manage accounts payable processes, ensuring timely and accurate payment processing for carriers and vendors
• Oversee credit risk assessment for customer accounts and establish appropriate credit limits and terms
• Monitor and analyze key performance indicators, including revenue per load, gross margin trends, and operating ratios

Strategic Planning & Advisory:

• Partner with executive leadership to develop financial strategies supporting business expansion and market penetration
• Provide financial guidance on carrier network development, customer acquisition costs, and technology investments
• Evaluate potential acquisitions, partnerships, or new service offerings through comprehensive financial analysis
• Develop pricing strategies that balance market competitiveness with profitability targets

Compliance & Risk Management:

• Ensure compliance with transportation industry regulations, including FMCSA requirements and freight broker bond obligations
• Manage relationships with surety bond providers and insurance carriers
• Oversee financial aspects of carrier onboarding, including insurance verification and contractual compliance
• Implement internal controls specific to freight brokerage operations

Reporting & Systems Management:

• Prepare monthly, quarterly, and annual financial reports with industry-specific metrics and benchmarks
• Lead month-end close processes, ensuring timely and accurate financial reporting
• Maintain journal entries and general ledger responsibilities, ensuring proper documentation and accuracy
• Interface with LoadStop, our (TMS), to ensure accurate financial data capture
• Develop dashboards and reporting tools for real-time visibility into financial performance
• Coordinate with external auditors and tax professionals on industry-specific matters

Qualifications:
The ideal candidate should have

• Minimum 5 years experience as a Financial Controller or senior finance leader within a freight brokerage
• Ability to lead and develop our accounting and finance team
• Relevant, documented freight brokerage experience and strong understanding of freight brokerage accounting principles and financial operations
• Relevant experience working with factoring companies and managing the accounting and cash flow implications of factoring relationships.
• Advanced QuickBooks experience
• Proven track record in financial analysis, budgeting, and forecasting
• Strong knowledge of US GAAP and financial reporting standards
• Strong analytical and problem-solving skills, with the ability to identify areas for improvement and implement corrective actions
• Bachelor's or Master's degree in Accounting, Finance, a related field or equivalent experience
• Certified Public Accountant (CPA) certification preferred, not required
• Strong communication and interpersonal skills, with the ability to collaborate with cross-functional teams

_____________________________________________________________________________________________

Preferred Qualifications:

• CFO or Sr Director of Finance experience
• CPA candidate
• Familiarity with Transportation Management Systems (TMS) LoadStop
• Understanding of FMCSA regulations and freight broker licensing requirements
• Experience with commission-based compensation structures and sales performance metrics

What We Offer:

• Competitive base salary, commensurate with experience. Range shown flexibility at different levels (Manager, Sr. Manager, Director, etc.) and based on applicant's experience/knowledge/business acumen in a freight brokerage environment
• Performance-based bonus structure
• Health, dental, and vision insurance
• Professional development opportunities

Opportunity to shape financial strategy in a high-growth environment
Location: Chicago, IL (Downtown) – 100% Onsite Full-time

Apply here or submit your resume and cover letter detailing your freight brokerage financial experience to Lace@ShipRoots.com.

We are an equal opportunity employer committed to building a diverse and inclusive team. Qualified Women, Minorities, and members of the Pride community are encouraged to apply!

No recruiters please – Candidates only.

Job Type: Full-time

Base Pay: $90,000.00 - $120,000.00 per year

Benefits:

• Dental insurance
• Health insurance
• Life insurance
• Paid time off
• Vision insurance

Application Question(s):

• Will you now or anytime in the future require sponsorship to maintain your employment with us?

Experience:

• QuickBooks: 5 years (Required)
• Freight Brokerage Accounting: 5 years (Required)
• Profit & loss: 5 years (Required)
• General ledger accounting: 5 years (Required)

Language:

• English (Required)

Work Location: In person