VP, Transaction Advisory

Chief Rebel is building the intelligence layer for small-business acquisition finance. Today, lenders repeatedly reconstruct the same analysis for every acquisition: financial normalization, valuation, debt-service capacity, buyer risk, deal structure, and credit underwriting. After close, much of that intelligence gets trapped in static files. Chief Rebel turns that fragmented process into a living credit record. Before close, we help lenders understand what a business is worth, whether an acquisition is financeable, and how the deal should be underwritten. After close, we keep the financial data connected so lenders can monitor how the business is actually performing. Over time, this creates something that doesn’t really exist today: a longitudinal dataset connecting the business, buyer, purchase price, capital structure, underwriting decision, and actual outcome. We have paying customers and funding. The Role We’re looking for a Head of M&A Finance to own the financial and transaction expertise behind Chief Rebel’s platform. You’ll help define how we analyze private-company financials, conduct Quality of Earnings & valuations, and translate that work into analysis lenders can trust. This is a hands-on role with significant ownership. You’ll work directly with our CEO, product team, lenders, underwriters, and transaction professionals while reviewing real acquisition opportunities and helping shape the financial standards behind our product. Your core challenge is: What is this business actually earning, what is it worth, and how should a lender think about financing the acquisition? What You’ll Build You’ll own and help establish the financial standards behind Chief Rebel across areas including: Quality of Earnings and financial due diligence Normalized EBITDA and SDE analysis Add-back and normalization assessment Working-capital and cash-flow analysis Business valuation and valuation preparation Debt-service capacity and leverage analysis Customer concentration and revenue-quality analysis Financial statement and accounting-quality review Credit and acquisition-finance analysis Transaction and lender-facing financial analysis Review and quality control of financial outputsIdentification of issues requiring additional diligence or professional judgment Repeatable analytical frameworks that can scale across a high volume of transactions You’ll work closely with our CEO, product team, and customers to ensure Chief Rebel’s outputs reflect the judgment of an experienced transaction professional and can be trusted by sophisticated lenders. What You Bring We’re looking for someone with approximately 4–6 years of experience across small business accounting, transaction advisory, valuation, and/or credit. An ideal background might include starting in audit or assurance before moving into Transaction Advisory Services, Financial Due Diligence, Quality of Earnings, or Valuation. Strong candidates will have meaningful experience in several of the following: Quality of Earnings Transaction Advisory Services Business valuation Audit or assurance Normalized EBITDA and SDE Working-capital analysis Private-company financial analysis Lower-middle-market or small-business transactions Commercial credit or underwriting SBA or acquisition financing Debt-service and leverage analysis Credit memo preparation or review An active CPA with plan to test for CVA, ABV, ASA, or other relevant valuation credentials are required. Experience working directly acquisition financing or evaluating transactions from a credit perspective is particularly interesting to us. What Matters Most You know Quality of Earnings. You can get into the details of a company’s financials, understand what is actually driving earnings, and distinguish defensible adjustments from aggressive ones. You understand valuation. You know how privately held businesses are valued and can identify the assumptions that actually matter. You understand the lender’s perspective. You can look beyond purchase price and EBITDA to think about cash flow, leverage, DSCR, liquidity, downside protection, and repayment risk. You have strong accounting judgment. You’re comfortable working with imperfect private-company financials and know when something doesn’t make sense. You’re still hands-on. You don’t want to simply manage outside advisors. You’re comfortable reviewing financial statements, digging through diligence, building analyses, and forming your own view. You can communicate your conclusions. You can take complicated financial issues and explain what matters to a lender, buyer, or investment professional. You think like an owner. You want meaningful ownership, ambiguity, customer exposure, and responsibility for helping build a company, not just completing engagements. Why This Is Interesting Traditional transaction advisory work is episodic. You analyze a business, deliver the QoE or valuation, close the engagement, and move on. At Chief Rebel, you have the opportunity to take the judgment developed across dozens or hundreds of engagements and help build something that improves how small-business acquisitions are analyzed and financed at scale. You’ll also see what happens after the transaction closes. The opportunity is to connect transaction analysis, underwriting, and actual business performance in a way that traditional advisory work rarely allows. Instead of delivering a report and moving on, you’ll help build the financial standard that sits at the center of the transaction. What Success Looks Like Over the first 12 months, you’ll help us: Establish rigorous standards for QoE, valuation, and transaction financial analysis Review hundreds of real small-business acquisition opportunities Improve the quality and consistency of financial analysis produced through Chief Rebel Develop repeatable processes for evaluating normalized earnings, valuation, cash flow, and debt capacity Work directly with lenders and underwriters to understand and improve their workflows Help Chief Rebel earn the trust of sophisticated credit professionals Build relationships across the lending, valuation, and transaction advisory ecosystem Help recruit and develop the finance and transaction-analysis function as we grow Who You’ll Work With Our CEO has lived the workflow we’re rebuilding, including acquiring and exiting an $8M-revenue business through SBA 7(a), brokering millions in transactions, and advising more than 100 business acquisitions. You’ll work alongside our CEO with clear ownership of Chief Rebel’s financial analysis, valuation +QoE, and transaction standards. Compensation and Ownership $110K-130K base + equity, depending on experience, commitment, and fit. We’re looking for someone who wants to take the judgment they’ve developed in audit, transaction advisory, QoE, valuation, or credit and use it to build the financial foundation for how small-business acquisitions are analyzed and financed. #J-18808-Ljbffr Chief Rebel