Position summary
The General Counsel & Chief Financial Officer is the senior legal and financial officer for a privately held group of home health care, aviation, aircraft services, and affiliated operating and real estate entities. Reporting directly to the owner, this executive owns the legal function and the finance function outright — governance, contracts, regulatory coordination, and risk on one side; reporting, treasury, credit, tax coordination, and internal control on the other.
This is a build role, not a maintenance role. The successful candidate will be the first person to hold either seat and will design both functions from the ground up while operating hands-on. Comfort moving between drafting an aircraft purchase agreement in the morning and rebuilding a thirteen-week cash forecast in the afternoon is not optional — it is the job.
Principal responsibilities — Legal (approximately 40%)
Governance and entity management
- Serve as principal legal advisor to the owner across all entities in the group
- Maintain corporate records for every entity: minute books, resolutions, consents, operating and shareholder agreements, capitalization records, and annual state filings
- Advise on entity structure, formation, and dissolution in coordination with outside tax counsel and the outside CPA firm
- Document and monitor intercompany and related-party arrangements so they are defensible on audit and in a credit review
Commercial contracting
- Draft, negotiate, and administer aircraft purchase and sale agreements, letters of intent, escrow instructions, and delivery documentation
- Negotiate hangar leases and subleases, ground leases, FBO agreements, and facility contracts
- Structure and paper aircraft management agreements, dry-lease and time-share arrangements, charter agreements, and interchange agreements
- Handle maintenance, MRO, avionics, and parts supply contracts, including warranty and turnaround-time terms
- Own the customer and vendor master agreement templates, NDAs, and the contract approval workflow
Aviation regulatory
- Coordinate FAA registration, title, lien releases, and international registry filings with aviation title and escrow counsel
- Advise on Part 91 versus Part 135 operations, operational control, and truth-in-leasing compliance
- Manage regulatory aspects of air carrier certificate acquisitions and transfers, including pre-acquisition due diligence and FAA coordination
- Coordinate with specialized outside aviation counsel; own the scope, budget, and quality of that relationship
Transactions, employment, risk, and disputes
- Lead legal workstreams on acquisitions and dispositions: diligence, purchase agreements, disclosure schedules, closing, and integration
- Own employment law compliance — handbook, classification, wage and hour, offer letters, restrictive covenants, separations, and agency responses
- Place and renew hull, liability, property, cyber, and employment practices coverage; review indemnity, insurance, and limitation-of-liability terms in every material contract; manage claims
- Manage litigation and disputes, including outside counsel selection, budgets, litigation holds, and settlement recommendations
- Build and maintain the compliance program: conflicts, records retention, data privacy, and policy library
Principal responsibilities — Finance (approximately 50%)
Reporting and close
- Own the monthly close across all entities and deliver consolidated and combining financial statements on a defined calendar
- Perform intercompany reconciliation and elimination; resolve related-party balances on a current basis rather than at year end
- Establish the reporting package the owner actually uses to run the business — entity-level and departmental P&L, balance sheet, and cash flow
- Coordinate the annual outside accounting engagement and the year-end tax workpaper package
Treasury, credit, and lender relations
- Own the global cash flow package used by lenders. Credit for aircraft and equipment at this scale is underwritten on the owner’s global cash flow across all entities and personal returns, not on the cash flow of the financed asset. Building and maintaining a lender-ready global cash flow schedule that ties entity statements, K-1s, and personal returns is a core deliverable of this role.
- Manage daily cash position, concentration and sweep arrangements, debt service scheduling, and borrowing base reporting
- Negotiate and document credit facilities, term debt, and equipment and aircraft financing; evaluate lease versus buy and financing structure alternatives
- Prepare covenant compliance certificates and forecast covenant headroom forward, so a covenant issue is identified a quarter early rather than at testing
- Own banking, surety, and insurance broker relationships
Planning and asset economics
- Build the annual budget, rolling forecast, and thirteen-week cash flow
- Model aircraft economics: direct operating cost per flight hour, fixed versus variable cost structure, utilization and breakeven, charter revenue offset, and residual value and exit scenarios, benchmarked to recognized industry cost data
- Evaluate capital projects, acquisitions, and hangar and facility investments on a defensible return basis
Tax, control, and systems
- Coordinate tax planning and compliance with the outside CPA firm across entity structure, S-corporation matters and reasonable compensation, depreciation and cost recovery elections, passive activity and material participation, and state apportionment
- Manage aviation-specific tax exposure in coordination with counsel and the CPA firm: federal excise tax on air transportation, sales and use tax on aircraft and parts, and imputation for personal use of company aircraft
- Design and monitor internal controls — approval matrices, segregation of duties, disbursement controls, and fraud prevention
- Own the accounting platform and reporting stack; drive automation of recurring reporting
- Hire, lead, and develop the accounting team
Principal responsibilities — Executive and strategic (approximately 10%)
- Serve as a principal advisor to the owner on capital allocation, acquisitions, and structure
- Prepare materials for lenders, insurers, and the owner’s advisory group
- Support succession and estate planning coordination with the owner’s outside advisors as directed
Required qualifications
- Juris Doctor from an ABA-accredited law school; active license in good standing; admitted in Indiana or eligible for admission or registration as in-house counsel in Indiana
- Ten or more years of combined professional experience, including at least five years in a senior legal role and demonstrated ownership of a finance function as Controller, CFO, VP Finance, or equivalent
- Demonstrated command of GAAP, financial statement preparation, and cash flow management — this is a hands-on finance seat, not an oversight seat
- Track record negotiating and closing substantial commercial contracts and asset transactions
- Direct experience with bank credit facilities, covenant compliance, and lender relationships
- Experience in a closely held or family-owned business environment, with the judgment that setting requires
Preferred qualifications
- CPA, CMA, MBA, or LL.M. in Taxation
- Aviation industry experience — Part 91 or Part 135 operations, aircraft transactions, FAA regulatory matters, or aviation finance
- Experience with multi-entity structures, intercompany accounting, and related-party transactions
- Buy-side or sell-side M&A closing experience
- Prior experience as the first person in a newly created executive seat
Competencies
- Two-hat discipline. Knows at all times which role he or she is occupying, and understands why that distinction matters for privilege and for control.
- Absolute discretion. Will hold personal, financial, and strategic information for the owner and the family.
- Hands-on orientation. Will build the schedule personally rather than wait for staff capacity that does not yet exist.
- Commercial judgment. Distinguishes real risk from theoretical risk and gives the owner a recommendation, not a list of considerations.
- Plain communication. Explains a covenant, a lease structure, or a tax exposure to a non-financial owner in terms that support a decision.
Compensation and terms
Base salary range of $260,000 to $340,000, commensurate with experience and credentials, plus an annual performance incentive targeted at 20% to 35% of base. Total target cash compensation of approximately $315,000 to $450,000. Benefits include health, dental, and vision coverage, retirement plan participation, bar dues and continuing legal and accounting education, and vehicle or travel allowance.
