Multi-Entity Accountant & Compliance Manager

Senior Accountant / Financial Operations Manager (Multi-Entity Business Operations)

Company: Transportation & Multi-Business Operations Group
Location: Remote
Job Type: Part-Time / Independent Contractor (1099)
Relationship Goal: Long-Term Growth Position
Compensation: Starting at $500/month with long-term growth potential based on operational workload, company expansion, and financial growth

About Us

We are a growing multi-entity business group operating across several industries.

We are seeking a highly organized, trustworthy, and proactive Senior Accountant / Financial Operations Manager to help oversee the financial organization, bookkeeping, compliance, payroll coordination, tax preparation, and operational financial management of multiple affiliated entities under one ownership structure.

This is NOT a basic bookkeeping-only role.

We are looking for someone who can think ahead, maintain organization across multiple entities, monitor compliance obligations, and help ownership remain financially structured, operationally compliant, and loan-ready as the companies continue growing.

This role is ideal for someone experienced in:

• small business accounting
• multi-entity bookkeeping
• payroll administration
• tax preparation
• compliance monitoring
• financial operations management

Our Current Growth Stage

We want to be fully transparent regarding compensation expectations.

At this stage, ownership is aggressively reinvesting capital back into business growth, equipment acquisition, operations, staffing, and expansion opportunities across multiple entities.

Our current priority is maintaining clean financial operations while preserving capital for:

• equipment purchases
• operational growth
• business expansion
• funding opportunities
• lender readiness
• long-term scaling

We are specifically seeking someone who understands growth-stage businesses and can help strategically organize financials in a way that positions the companies for:

• larger funding opportunities
• stronger banking relationships
• equipment financing
• operational expansion
• and long-term business success

We are looking for a long-term relationship with someone who wants to grow alongside the companies as operations continue expanding.

Compensation is expected to increase as workload, revenues, financing opportunities, and operational scale continue growing over time.

Entities ManagedEntity 1

• 4 W2 Employees
• 1 Independent Contractor

Entity 2

• Single Member

Entity 3

• 1 Owner
• 1 W2 Employee

Entity 4

• 1 Owner
• 1 Independent Contractor

Entity 5

• Currently low operational activity

Entity 6

• Passive holding entity

Responsibilities

The selected candidate will be expected to assist with the following:

Bookkeeping & Financial Organization

• Monthly bookkeeping for all entities
• Expense categorization
• Profit & loss tracking
• Bank reconciliations
• Transaction organization
• Intercompany transaction tracking
• Financial cleanup when needed
• Monitoring business cash flow
• Maintaining organized financial records
• Assisting with budgeting and financial planning
• Maintaining clean financials suitable for lenders, banks, and financing requests
• Helping ensure each entity remains financially organized and loan-ready at all times

Payroll & Contractor Administration

• Process payroll
• Coordinate payroll taxes
• Maintain payroll records
• Manage W2 and 1099 tracking
• Ensure payroll compliance
• Assist with employee/contractor financial onboarding documentation when required

Tax Preparation & Filings

Prepare and coordinate:

• Business tax returns
• Personal tax returns
• Quarterly filings
• Payroll tax filings
• W2 filings
• 1099 filings
• Estimated tax planning when necessary

The selected candidate should be comfortable coordinating directly with tax preparation and filing responsibilities across multiple entities.

Compliance & Administrative Oversight

The selected candidate will also be expected to assist in monitoring and managing ongoing financial and compliance obligations for each entity, including but not limited to:

• Quarterly tax filings
• Payroll tax compliance
• Annual report tracking
• State business compliance requirements
• Multi-state operational filings where applicable
• Recordkeeping and document organization
• Monitoring filing deadlines
• Coordinating regarding government notices, penalties, audits, or compliance correspondence
• Helping ownership remain proactive regarding compliance obligations

This role is expected to operate proactively — not reactively.

We are looking for someone capable of helping ownership stay ahead of financial, tax, payroll, operational, and compliance responsibilities across multiple businesses.

Financial Operations Oversight

Help ownership understand:

• company profitability
• operational costs
• tax exposure
• financial organization
• growth planning
• financial risk
• lender readiness

Additional responsibilities may include:

• recommending better systems/workflows
• identifying operational inefficiencies
• improving bookkeeping structure
• helping maintain separation between entities
• assisting with long-term financial organization
• helping prepare financial documentation for funding opportunities when needed
• assisting ownership in building stronger financial positioning for future business growth and financing opportunities

Preferred Software Experience

Experience with any of the following is preferred:

• QuickBooks
• Xero
• Gusto
• ADP
• Excel
• Google Sheets

Ideal Candidate

We are looking for someone who:

• Understands multi-entity business structures
• Is highly organized
• Is trustworthy and professional
• Can operate independently
• Has strong communication skills
• Understands startup and growth-stage businesses
• Is proactive with deadlines and compliance
• Is comfortable helping build financial systems from the ground up
• Maintains strict confidentiality
• Can think beyond simple bookkeeping tasks
• Understands the importance of maintaining lender-ready financial records
• Understands how organized financials can help businesses qualify for larger funding opportunities

Important Notes

• This role will begin as a remote independent contractor (1099) position.
• This is a startup-stage compensation structure with long-term growth potential.
• We prefer someone seeking a long-term relationship rather than a short-term bookkeeping project.
• Compensation is expected to increase as operations, workload, revenues, and company growth continue expanding.
• We are looking for someone interested in helping build long-term operational and financial success across multiple entities.

To Apply

Please submit:

• Resume
• Relevant experience
• Industries worked in
• Software proficiency
• Availability
• Expected long-term compensation goals

Please also explain:

• Your experience managing multiple companies under one ownership structure
• Your experience handling payroll and year-end filings
• Your experience managing compliance deadlines and recurring filings
• Your experience preparing businesses for financing or lender review
• What accounting software you recommend for a growing multi-company operation

Company Contact

Jordan Brown

careers@insuredtranspo.com

Pay: $500.00 per month

Work Location: Remote