Controller

MedicareSchool (“Company”)

Reports to: Chief Financial Officer

Location: Overland Park, KS (on-site)

Compensation: $100K–$125K

About MedicareSchool.com

MedicareSchool.com has spent 17 years establishing itself as the most trusted name in Medicare

education. With approximately 400,000 YouTube subscribers and more than 70,000 clients, the

Company has built a content-driven distribution model that converts consumer trust into one of

the most efficient client-acquisition engines in the industry. That foundation has since expanded

beyond Medicare brokerage into annuities and retirement asset management, broadening the

Company's value proposition and addressable market.

MedicareSchool.com is entering its most significant growth phase, and the Company is building the

financial and accounting infrastructure required to support a larger, more complex organization.

The Company is seeking a Controller to lead the conversion to full GAAP reporting, its first

external financial statement audit, and the buildout of a scalable accounting function.

The Operating Mandate

Today, the CFO carries primary responsibility for accounting. The Controller will take ownership

of the accounting function and establish the policies, processes, controls, systems, and team

required to operate at the standard of a scaled, professionally managed business. The CFO will

remain closely involved through GAAP conversion, technical accounting decisions, and first

audit, after which the Controller is expected to fully own the function.

The accounting is not straightforward. Renewal commission streams, chargebacks and

clawbacks, and capitalized acquisition costs create meaningful judgment under ASC 606 and

ASC 340-40. Equally important is the operational core of the close: reconciling commissions

receivable from carriers with commissions payable to producers across carrier statements,

splits, overrides, chargebacks, and cash collections. Getting these areas right is foundational to

reliable reporting and future diligence readiness.

Areas of Ownership

• GAAP Conversion & Technical Accounting: Assess current practices, identify gaps, execute the conversion to GAAP, and establish documented accounting policies, with particular focus on revenue recognition, variable consideration, commission streams, chargebacks, and capitalized acquisition costs.
• Commission Accounting: Build the schedules, reconciliations, and controls governing carrier commissions receivable and producer commissions payable, including carrier statements, splits and overrides, chargeback estimation, collections, and true-ups.
• Monthly Close & Financial Reporting: Establish a disciplined close calendar, reconciled balance sheet, accrual and review procedures, and accurate GAAP financial statements and reporting for the CFO, Board, and ownership group.
• Audit Readiness: Lead the first external financial statement audit and own the process thereafter, including timelines, PBC requests, supporting schedules, issue resolution, and a repeatable approach that keeps the business continuously audit-ready.
• Systems, Processes & Controls: Evaluate and improve the chart of accounts, general ledger structure, approval workflows, segregation of duties, reconciliations, and documentation standards; automate manual work where appropriate without adding unnecessary bureaucracy.
• Accounting Function: Own GL, AP, AR, treasury, payroll accounting, revenue, accruals, fixed assets, prepaids, and financial statement preparation. The role will remain hands-on initially and will define and build the accounting team as scale and complexity justify it.

Year One Priorities

The first year is about establishing a durable accounting foundation. The Controller will learn the

underlying economics and transaction flows, complete the GAAP conversion and first audit, and

create the close, reconciliations, policies, and controls required for repeatable reporting.

By the end of the first 12 to 18 months:

• GAAP financial statements are produced on a reliable monthly close calendar, with documented policies and reconciled key balance sheet accounts.
• Commission receivables and producer payables are fully reconciled and supportable.
• The initial external audit is complete and a repeatable audit-readiness process is in place.
• A practical control environment is operating consistently, and the CFO is no longer carrying the day-to-day accounting function.
• The Company is building a clean, audited financial history that will support future financing, diligence, and strategic activity.

The Candidate

Required:

• Controller, Assistant Controller, or comparable senior accounting leadership experience, with strong command of the monthly close, financial statements, balance sheet reconciliations, and core accounting operations.
• Direct experience converting a private company to GAAP reporting and preparing it for a first external financial statement audit.
• Strong technical accounting capabilities, particularly revenue recognition and other judgment-intensive areas.
• Experience working directly with external auditors.
• Track record building accounting policies, controls, processes, and reporting infrastructure in a growing or professionalizing organization.
• Comfort operating as a hands-on leader while the function and team are still being built.

Strongly Preferred:

• CPA, ideally combined with public accounting and meaningful private company operating experience.
• Experience with commission accounting or recurring / renewal-based revenue models, particularly in insurance, brokerage, agency, or financial services.
• Familiarity with ASC 606 and ASC 340-40, including variable consideration and commission capitalization.
• Experience building an accounting function in advance of a transaction, financing, or diligence process.

To apply: Please send your resume to [email protected].

MedicareSchool.com is an equal opportunity employer.