Senior Staff Accountant

Own the details behind a diverse, multi-entity investment portfolio

Full-Time | Hybrid |Periodic Travel to Rockford, Illinois| Reports to Controller / Managing Partner

Rock Oak Capital Partners oversees and supports a diversified portfolio of operating businesses and investments across healthcare, commercial real estate, hospitality, software and private aviation.

The family office finance team supports multiple operating entities, holding companies and investments, each with different transaction flows, reporting requirements and operating considerations. That creates an opportunity for accounting professionals who enjoy understanding how businesses work, solving problems and maintaining accurate financial information across a complex organization.

Rock Oak Capital Partners is seeking a hands-on, detail-oriented Senior Staff Accountant to support general ledger accounting, month-end close, treasury operations, reconciliations and tax preparation across the portfolio.

This role will be an important part of the day-to-day financial operation of the family office. The Senior Staff Accountant will work across multiple entities, maintain accurate and audit-ready financial records, investigate discrepancies and help ensure that transactions move cleanly between operating companies and holding entities.

The position is well suited for an accountant who enjoys variety and wants broader exposure than is typically available within a single-company accounting department. As the family office accounting function continues to expand, the team is also expected to assume responsibility for additional portfolio-company accounting currently supported through external resources.

The strongest candidate will be technically solid, highly organized and exceptionally attentive to detail. This person will be comfortable working across numerous entities and accounts while maintaining accuracy, meeting deadlines and recognizing when something does not look right.

We are looking for someone who takes ownership of their work, enjoys digging into discrepancies and can operate effectively in an entrepreneurial environment where priorities may cross industries and business types.

• Prepare journal entries, account reconciliations and supporting schedules across multiple operating companies, holding companies and investment entities.
• Support timely and accurate month-end and year-end close, including fixed assets, accruals, prepaids and intercompany balances.
• Investigate discrepancies and maintain accurate, audit-ready financial records.

• Monitor daily banking activity and support cash management, ACH/wire transactions and intercompany funding.
• Reconcile merchant/POS deposits, healthcare collections and other operating activity across the portfolio.
• Support accounts payable, expense allocations and recurring accounting workflows.
• Support accounting and reconciliations across Rock Oak's healthcare, real estate, hospitality, software and aviation holdings.
• Maintain supporting schedules for portfolio-specific activity such as leases, tenant payments, aircraft expenses and other operating transactions.

• Prepare schedules, trial balances and supporting documentation for external auditors and tax preparers.
• Assist with 1099 reporting and applicable sales, use, property and other state and local tax filings.

• Perform day-to-day accounting activities in Net Suite and maintain consistent accounting practices across entities.
• Identify opportunities to improve reconciliations, documentation and accounting workflows.