Controller

The Opportunity

Rock Oak Capital Partners is seeking an experienced, hands-on Controller to lead accounting operations, financial close, reporting, treasury management, tax coordination and financial controls across the Rock Oak family office and investment portfolio.

The Controller will assume meaningful ownership of a function currently receiving substantial hands-on involvement from senior Rock Oak leadership. This individual will be expected not simply to maintain the books, but to create structure around them - building reliable processes, improving financial visibility, strengthening controls and ensuring that multiple entities operate within a consistent and disciplined accounting framework.

This is an unusually broad Controller opportunity. The portfolio includes operating businesses and investments across healthcare, real estate, hospitality, SaaS and private aviation, creating a combination of accounting, treasury and business issues rarely found within a traditional corporate Controller role. 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 an experienced Controller or Assistant Controller who combines strong technical accounting fundamentals with the ability to operate autonomously in a complex, entrepreneurial environment.

This person must be comfortable moving between detail and strategy: reviewing an account reconciliation or intercompany entry one moment and discussing liquidity, cash requirements, financial performance or an acquisition with senior leadership the next.

We are looking for a builder rather than a caretaker - someone who sees opportunities to create better processes, stronger controls and clearer financial reporting and takes ownership of making those improvements happen.

Key Responsibilities:

Financial Close, Consolidation & Reporting

• Lead month-end, quarter-end and year-end close across Rock Oak's operating companies, holding companies and investment entities.
• Oversee entity-level and consolidated financial reporting, intercompany eliminations, allocations and variance analysis.
• Establish consistent close processes and maintain strong financial reporting disciplines across the portfolio.

Treasury Leadership & Liquidity Management

• Lead treasury management across the portfolio, including cash positioning, intercompany funding, distributions and debt service.
• Develop and maintain a rolling 13-week cash-flow forecast and provide leadership with clear visibility into liquidity needs.
• Manage banking relationships, treasury services and appropriate controls around cash movement.

Tax, Audit & External Accounting Coordination

• Serve as the primary accounting liaison to external CPA firms, tax advisors and auditors.
• Coordinate year-end workpapers, tax preparation, audit activity and applicable state and local compliance.
• Review key financial and tax deliverables for accuracy and completeness.

Accounting Leadership & Internal Controls

• Lead and develop the accounting team, establishing clear ownership, deadlines and accountability.
• Design and maintain effective accounting policies, approval processes and internal controls appropriate for a multi-entity family office.

Systems & Process Improvement

• Own and continuously improve accounting processes and reporting within NetSuite.
• Identify opportunities to automate manual work, strengthen controls and improve reporting consistency across entities.

Strategic & Transaction Support

• Provide financial analysis and modeling to Rock Oak's Managing Partners.
• Support acquisitions, dispositions, new entity formations and other strategic or investment-related activity.

Required Experience and Capabilities:

• 7-12+ years of progressive accounting and financial management experience.
• At least three years in a Controller, Assistant Controller or comparable accounting leadership position.
• Experience leading a team of accounting professionals.
• Bachelor's degree in Accounting or a closely related field.
• Demonstrated expertise in multi-entity accounting, consolidations and intercompany transactions.
• Strong technical accounting foundation and experience overseeing month-end and year-end close.
• Meaningful treasury and cash-management experience.
• Experience working directly with external auditors, CPA firms and tax advisors.
• Strong ERP experience; NetSuite experience is strongly preferred.
• Advanced Microsoft Excel and financial analysis capabilities.
• Demonstrated ability to design and improve accounting processes and internal controls.
• Strong leadership skills and experience directing or developing accounting staff.
• Ability to operate independently, exercise sound judgment and manage complex priorities with limited oversight.
• Excellent communication skills and the ability to work directly with Managing Partners and senior operating leaders.
• Absolute discretion when working with confidential financial, investment and family office information.

Relevant and Preferred Background

• Active CPA strongly preferred.
• Combination of public accounting and private industry experience.
• Family office, investment office or multi-entity corporate accounting experience.
• Experience supporting a diversified portfolio of operating companies.
• Healthcare industry accounting experience.
• Exposure to commercial real estate, hospitality, SaaS or aviation accounting.
• Experience managing accounting during acquisitions, divestitures or other business transactions.
• Experience implementing or optimizing NetSuite in a multi-entity environment.
• Experience developing cash-flow forecasting and portfolio-level liquidity reporting.

Why Join Rock Oak?

• Lead a uniquely diverse financial environment. Oversee accounting and treasury across operating businesses and investments spanning multiple industries and asset classes.
• Build, do not simply maintain. Rock Oak is continuing to develop its family office infrastructure, giving the Controller the opportunity to shape processes, systems, controls and reporting rather than inherit a fully mature corporate bureaucracy.
• Work directly with ownership. This role will have significant interaction with Rock Oak's Managing Partners and meaningful influence over how financial information is used to make decisions.
• See the whole picture. The Controller will have visibility across operating companies, investments, cash strategy, tax matters and transactions - providing a broader perspective than most traditional corporate Controller positions.

Location & Work Environment

This is a mostly remote 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...likely once or twice a month.

Compensation

Target Base Salary: $117,000-$157,000

Target Bonus Opportunity: 10%-15%

Actual compensation will depend on experience, capabilities and the breadth of responsibility the successful candidate is prepared to assume.