Controller | Multi-Entity Portfolio

Build the Financial Foundation for a Growing Portfolio of Businesses Most Controller roles focus on reporting the past. This one is about helping shape the future. We are building a long-term portfolio of businesses and investments—not simply operating one company. Today, our holdings include Kids Art Box, commercial and residential real estate, a neighborhood grocery store, land investments, and additional ventures that continue to grow. In the near future, the portfolio will expand to include additional industrial and commercial real estate, operating businesses, and an aircraft leasing company. We're looking for a Controller who wants to be more than an accountant. This is an opportunity to become the financial partner to an entrepreneurial owner who enjoys building businesses, acquiring new opportunities, and solving complex problems. You'll work directly with the owner on virtually every significant financial decision—from evaluating acquisitions and launching new businesses to improving existing operations, allocating capital, and protecting the long-term financial health of the portfolio. Your role is to provide the financial discipline that ensures each venture is built on a solid foundation, remains profitable, and has the systems in place to scale successfully. We love building new businesses—but they need to become profitable businesses, not expensive hobbies. You'll play a critical role in making that happen. As our portfolio grows, this position has a clear path to becoming the senior financial leader for the organization, with responsibility for building and leading the accounting and finance team. Why This Opportunity Is Different This isn't a traditional family office or a role focused on maintaining a mature portfolio of investments. The owner has spent his career building businesses—from startups to large operating companies. Over the years, he has founded, acquired, and grown dozens of businesses. Two of those businesses were built from the ground up into publicly traded companies with market capitalizations exceeding $7.5 billion each. While this role will not support those two public companies, it reflects the type of entrepreneurial environment you'll be joining. New ideas become new companies. Businesses are acquired, improved, and expanded. Real estate is developed. New opportunities are constantly evaluated. We're looking for someone who enjoys building alongside an entrepreneur—someone who finds satisfaction in creating financial structure, improving operations, and helping transform promising ideas into profitable, well-managed businesses. If your ideal job is simply closing the books each month, this probably isn't it. If you want to help build the next great business while creating the financial systems that make sustainable growth possible, we'd love to meet you. Location Chattanooga, Tennessee (In-Person) This is an in-person position based in Chattanooga, Tennessee. We believe the best Controller is deeply engaged in the businesses they support—not just reviewing financial statements from a distance. You'll regularly interact with managers, visit operating businesses, understand how each company functions, and help turn financial information into better business decisions. If you enjoy partnering with leadership, solving problems collaboratively, and seeing firsthand how businesses operate, you'll thrive in this environment. What You'll DoOwn the Financial Operations Oversee accounting and financial operations across multiple companies and legal entities. Evaluate, manage, and improve the current outsourced bookkeeping function. Determine the long-term accounting structure, including whether bookkeeping should remain outsourced or be brought in-house. Perform accounting functions directly where appropriate while building scalable processes. Ensure accurate financial records, reconciliations, journal entries, and intercompany accounting. Lead timely month-end and year-end closes for every company. Coordinate with outside accounting firms for tax preparation and annual filings. Maintain consistent accounting policies and reporting standards across the portfolio. Deliver Financial Insight Prepare concise weekly executive reports summarizing cash position, profitability, key metrics, upcoming issues, and opportunities. Produce accurate monthly financial statements for every business. Develop dashboards and KPIs that help management understand what is driving financial performance. Analyze financial trends and identify opportunities to improve profitability and operational efficiency. Present financial information in a way that helps non-financial managers make better decisions. Protect Cash & Plan Ahead Manage cash flow across the portfolio. Prepare rolling cash flow forecasts. Review and approve accounts payable before payment. Monitor working capital and liquidity across all businesses. Recommend financing, capital allocation, and cash management strategies when appropriate. Help ensure each business has the financial resources necessary to grow responsibly. Partner with Business Leaders Work alongside ownership and business managers to develop annual budgets and ongoing forecasts. Help managers understand the financial impact of operational decisions. Evaluate pricing, margins, labor, inventory, and other business drivers to improve profitability. Provide financial analysis for acquisitions, new ventures, capital projects, and investment opportunities. Participate in the evaluation, financial due diligence, structuring, and integration of future business, real estate, and other investment acquisitions. Serve as a trusted advisor by providing objective financial guidance—even when it means challenging assumptions. Build Better Systems Strengthen internal controls and financial reporting. Standardize accounting procedures across all companies. Improve reporting speed, accuracy, and usefulness. Evaluate existing accounting systems and recommend improvements as the portfolio grows. Lead future accounting system implementations or migrations where appropriate. Build scalable financial systems capable of supporting future acquisitions and continued growth. Build the Finance Team Help determine the long-term accounting organization. Recruit, hire, train, and manage bookkeeping and accounting staff as the organization grows. Develop processes that allow the finance function to scale efficiently. Who Will Thrive Here You may be an excellent fit if you: Love bringing order to growing businesses. Enjoy creating systems instead of simply following them. Think like an owner and naturally look for ways to improve profitability. Are equally comfortable reviewing journal entries and discussing business strategy. Like variety and enjoy learning how different businesses operate. Enjoy solving problems rather than repeating the same routine every month. Are proactive and naturally identify issues before they become problems. Want your work to directly influence business decisions instead of simply reporting historical results. Get excited about helping build a long-term portfolio of successful businesses. Qualifications Experience managing multiple companies, business units, or legal entities is highly desirable. Strong knowledge of GAAP, financial reporting, internal controls, budgeting, forecasting, and cash management. Strong proficiency with QuickBooks Enterprise is highly preferred. Our companies currently operate on QuickBooks Enterprise, and familiarity with the platform will allow you to make an immediate impact. As the organization grows, you'll help evaluate when individual businesses are ready to transition to more sophisticated ERP or accounting systems and play a key role in planning and implementing those upgrades. Advanced Microsoft Excel skills. Bachelor's degree in Accounting, Finance, or a related field, or equivalent professional experience. Seven or more years of progressive accounting experience, preferably including Controller or Assistant Controller responsibilities. Excellent analytical, organizational, and communication skills. High integrity, sound judgment, and exceptional attention to detail. Success in Your First Year Within your first year, you'll: Establish consistent, timely month-end closes across every company. Deliver reliable weekly financial reporting that ownership depends on. Implement rolling cash flow forecasting across the portfolio. Strengthen internal controls and financial processes. Optimize the bookkeeping function and establish clear accounting standards. Improve budgeting and forecasting throughout the organization. Build meaningful KPI reporting that helps drive better business decisions. Become the trusted financial partner to ownership. Growth Opportunity While the initial title is Controller, this role is intentionally designed with room to grow. As the portfolio expands through new businesses, real estate investments, and acquisitions, the successful candidate will have the opportunity to build the finance organization, hire and develop a team, modernize financial systems, and evolve into the senior financial executive responsible for the financial performance of an increasingly diverse group of businesses. If you're looking for a traditional Controller role where every month looks the same, this probably isn't it. If you're energized by entrepreneurship, enjoy building systems that scale, and want to help shape the future of a growing portfolio of businesses, we'd love to meet you. Pay: $90,000.00 - $125,000.00 per year Work Location: In person