Head of Capital Markets

ABOUT RAILRail is a Delaware C-Corp balance sheet lending company purchasing SMB receivables originated through marketplace platforms. We are building a capital-efficient, technology-driven lending platform with a lean team, leveraging AI underwriting, outsourced compliance, and BPO servicing. We are raising senior secured warehouse financing and preferred equity subordination to fund growth from launch to $500M in annual originations.THE ROLEYou will be the first capital markets hire and will own the entire funding stack - from financial modeling and lender origination through facility negotiation, closing, and ongoing compliance reporting. This is not a support role and it is not for someone who needs to be told what to do. You will sit at the table with warehouse lenders, family offices, and institutional investors, and you will be the person who builds the models they base their credit decisions on. You will work directly with the CEO on capital strategy and be a key voice in board-level discussions. We are looking for someone who is exceptionally sharp, moves fast, and has the intellectual horsepower to operate across financial modeling, legal negotiation, and investor relations simultaneously.RESPONSIBILITIESOwn the company financial model and FP&A function end-to-end: origination projections, portfolio roll-forward, payment waterfall, warehouse mechanics, P&L, cash flow, budgeting, and board reporting - maintaining it as the single source of truth for all capital raise and board discussionsBuild and maintain pro forma portfolio projections for each product channel (RBF, Term Loan, Card) including vintage-level performance tracking, collection curves, and chargeoff waterfallsLead warehouse facility origination: identify target lenders (banks, credit funds, specialty platforms), build relationships, prepare pitch materials, and manage the full diligence process through commitment letter and closingStructure and negotiate facility terms: advance rates, interest rates, covenants, concentration limits, eligibility criteria, borrowing base mechanics, and early amortization triggersSource and close preferred equity subordination: engage family offices and institutional investors, structure terms, and manage ongoing investor communicationsBuild and maintain lender reporting infrastructure: monthly borrowing base certificates, portfolio performance reports, covenant compliance dashboards, and quarterly investor updatesMonitor facility utilization and capacity planning: forecast when facilities need upsizing, negotiate accordion features, and manage facility scaling as origination volume growsPartner with the CEO on capital strategy: equity raise timing, balance sheet optimization, securitization pathways, and credit facility diversificationLead ABS takeout planning: build the analytical framework for term securitization, evaluate timing and execution strategy, and position the portfolio for rated deal issuanceStructure economics for channel partner and referral agreements, including commission structures, volume commitments, and holdback termsREQUIRED QUALIFICATIONS7+ years in capital markets, structured finance, or treasury at a specialty lending company, fintech lender, or credit fund - this is a senior role and we expect a senior track recordDirectly involved in closing at least one warehouse facility of $50M+ as borrower-side lead or a key member of the deal team - you have been through the full lifecycle from term sheet to closing docsDeep understanding of receivables-based lending economics: factor rates, MCA/RBF mechanics, payment waterfall structures, and SPV-level cash flow modelingExpert financial modeler: you have built warehouse facility models and pro forma portfolio projections that were reviewed by lender credit committees and used to set facility termsStrong relationships with warehouse lenders, credit funds, or institutional capital providers in the SMB lending or specialty finance space - you can pick up the phone and get a meetingComfortable operating in an early-stage environment with minimal support staff - you will build the function from scratch and that excites you, not intimidates youSTRONGLY PREFERREDCFA charterholder or MBA/MS Finance from a top-tier program (Ivy League, Stanford, MIT, Chicago Booth, Wharton, or equivalent)Prior role as VP/Director of Capital Markets, Treasury, or Structured Finance at an MCA, RBF, or SMB lending platform (OnDeck, Kapitus, Credibly, Libertas, Clearco, Pipe, or similar)Experience structuring facilities with both bank warehouse lenders and non-bank credit fundsExposure to credit card receivables funding, interchange economics, or BaaS/prepaid card programsUnderstanding of covenant negotiation from the borrower side - DSCR tests, concentration limits, delinquency triggers, and how to build headroom into facility structuresExperience with Column, Evolve, Celtic, or similar bank partnership infrastructureWHAT SETS THIS ROLE APARTFirst capital markets hire at a company with live marketplace distribution, existing origination partnerships, and a clear path to $500M+ in annual volume - you are not building a hypothetical businessDirect access to the CEO with no layers of management - you will shape capital strategy, not just execute itMeaningful equity in a capital-efficient business model with a lean team and outsourced operations - this is a founding-team level opportunityDual marketplace structure provides diversified origination that warehouse lenders value - your job is to translate this into best-in-class facility termsCOMPENSATION & BENEFITS$175,000-$215,000 base salary, depending on experienceMilestone bonuses tied to warehouse facility tranche closes, plus annual discretionary bonusFully remote with travel budget for lender meetings and industry conferences