The Opportunity:

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 Ideal Candidate:

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.

Key Responsibilities:

General Ledger & Month-End Close

• 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.

Treasury & Daily Accounting Operations

• 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.

Portfolio Accounting

• 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.

Tax, Audit & Compliance Support

• 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.

Systems & Process Improvement

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

Required Experience and Capabilities:

• 3-6 years of progressive accounting experience.
• Bachelor's degree in Accounting, Finance or a related field.
• Strong general ledger accounting and account reconciliation experience.
• Hands-on experience supporting month-end close.
• Experience working within an ERP or comprehensive accounting platform; NetSuite experience is strongly preferred.
• Intermediate to advanced Microsoft Excel skills, including pivot tables, XLOOKUP and complex formulas.
• Strong analytical and problem-solving skills with exceptional attention to detail.
• Ability to manage multiple entities, deadlines and priorities simultaneously.
• High degree of discretion and sound judgment when handling confidential financial information.
• Strong communication skills and a willingness to work collaboratively with accounting colleagues and business leaders.

Relevant and Preferred Background:

• Experience within a multi-entity corporate, family office, investment or portfolio company environment.
• Public accounting audit or tax experience.
• Healthcare accounting experience.
• Experience with intercompany transactions and allocations.
• Exposure to commercial real estate, hospitality, SaaS or other portfolio-company accounting.
• CPA eligibility, CPA candidacy or other relevant accounting certification.

Why Join Rock Oak?

• Gain unusually broad accounting exposure. Work across multiple businesses, asset classes and legal entities rather than spending your career inside a single operating company.
• Take meaningful ownership. This is a hands-on role where accuracy, judgment and follow-through matter, and strong performers will have significant visibility into the financial operation of the portfolio.
• Work directly with decision-makers. The accounting organization works closely with Rock Oak leadership and the operating businesses it supports.
• Help build the function. Rock Oak continues to develop its family office accounting infrastructure, creating opportunities to improve processes, strengthen reporting and help shape how the organization operates.

Location & Work Environment

This is a hybrid position with periodic travel to Rock Oak Capital Partners' family office in the Rockford, Illinois area for team meetings, planning sessions and other business needs.

Compensation

Target Base Salary: $85,000-$105,000
Target Bonus: 10%