Fractional Controller

About the RoleYou will be the senior financial leader for a growing rewards-technology business with enterprise partners, a member-facing marketplace, and a recent acquisition to absorb. You will build the models that support fundraising and partner deals, make sure the contracts Bookit signs are financially enforced, and oversee accounting so the books are accurate, timely, and investor-ready. You will work directly with the CEO and leadership team as a strategic partner.The ideal candidate understands how a scaling start-up organization should "see around the corner" of potential financial opportunities and hurdles and prepares the organization to meet them.What You'll DoBuild and maintain an integrated three-statement model (income, balance sheet, cash flows) with defensible assumptions, covering both the licensing of Bookit's B2BC white-labeled travel and experience booking platform and direct-to-member revenue streamsOversee Revenue recognition, including analyzing complex customer contracts, sales terms, and non-standard arrangements to determine proper revenue accounting treatment, to allow for complete PnL analysis.Ensure contract terms are financially enforced, including:Partner billing schedules, minimum commitments, revenue share and rewards-funding termsSupplier and inventory agreements, including pre-purchase commitments, cancellation and refund terms, and settlement timingRenewals, escalators, credits, and late feesRun recurring audits for revenue leakage, under-billing, margin erosion, missed renewals, and deviations from agreed termsPrepare diligence materials for investors and strategic partners, including data room financials, KPI packages, and unit economicsAs-needed fundraising support by developing models for use of proceeds, runway, dilution and cap table scenarios, valuation sensitivities, and moreModel prospective enterprise and white-label partner deals before signing:Margin waterfall from wholesale cost through merchant margin to the reward percentage funded back to membersRevenue share and fee structures, minimums, implementation costs, and partner-specific rewards fundingPoints issuance and redemption assumptions, including breakage and the cost of points liabilityCash timing between supplier payment, member or partner payment, and partner settlementWorking capital and inventory commitment exposure on pre-booked or pre-purchased inventoryRun base, upside, and downside scenarios to support go/no-go decisions on large or non-standard dealsSupport the CEO in investor conversations, board reporting, and financing strategy.Oversee order-to-cash and procure-to-pay across travel, experiential, and retail suppliers and enterprise partners, including aggregated partner billingReconcile transaction, points, and payments data across the platform, payment processors, suppliers, and the general ledgerSet approval thresholds and controls for discounts, credits, refunds, and non-standard termsAlign contract templates with what finance can operationally bill, reconcile, and collectOversee bookkeeping and accounting, whether in-house or outsourced, including the monthly close, reconciliations, and financial statement preparation including:Revenue recognition, including gross vs. net (principal vs. agent) presentation on travel and experiential salesLoyalty points and rewards liability, breakage, and deferred revenueInventory prepayments and supplier depositsLead accounting integration of the M&A activity: purchase accounting, entity consolidation, chart of accounts and systems alignment, and intercompany treatmentReview and approve monthly financials and deliver management reporting with variance analysisManage relationships with external accountants, auditors, and tax advisors, including sales and transient occupancy tax exposure on travel sales, multi-state and international tax, and payroll tax complianceOversee payroll, expense management, and benefits accounting in coordination with HRStrengthen internal controls and documentation, including readiness for enterprise partner security and vendor reviewsManage cash flow forecasting and working capital, including supplier payment timing and inventory exposureDefine and report key metrics: gross bookings, take rate, net revenue margin, points issued vs. redeemed, breakage, partner engagement and redemption rates, CAC, LTV, churn, burn multiple, and runwayWhat We're Looking For10+ years of progressive finance experience, including prior CFO, VP Finance, or Controller leadership.Demonstrated experience building fundraising models and supporting equity or debt raisesStrong command of revenue recognition (including principal vs. agent analysis), contract-driven billing, and accounting operationsAdvanced financial modeling skills; FP&A tool experience a plusExperience with modern accounting, billing, and payments systems (e.g., QuickBooks, Stripe, Bill.com)Experience with M&A integration, including purchase accounting and consolidationComfort working with founders, investors, enterprise partners, and outside counselAbility to work independently in a part-time, high-autonomy role.PreferredExperience in loyalty and rewards, travel or ticketing marketplaces, fintech, or B2B2C platformsExperience accounting for points, gift cards, or other stored-value liabilitiesExperience with enterprise partnerships involving banks, card issuers, or large consumer brandsCPA, CFA, or MBAExperience with growth-stage companies (Series A through C)BenefitsAs this is a part-time aka fractional role it is not benefits eligible.Location: Remote, Columbus, Ohio, United StatesJ-18808-Ljbffr