Controller (Fractional)

About Bookit

Bookit is revolutionizing the travel and loyalty industry as the next-generation B2B2C “super app” offering our brand clients and consumers unprecedented value on luxury travel as well as unforgettable VIP music, sports, and lifestyle experiences. Consumers save up to 70% when booking on our platform, earning universal rewards points that can be spent with over three million brand partners.

Envisioned as a “next-gen Expedia,” Bookit supports customer transactions in more than 3,000 cryptocurrencies as well as debit/credit cards and brand rewards points. Our SaaS technology infrastructure transforms the future of payments.

Learn more at bookit.com

About the Role

You 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 Do

• Build 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 streams
• Oversee 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 terms
• Supplier and inventory agreements, including pre-purchase commitments, cancellation and refund terms, and settlement timing
• Renewals, escalators, credits, and late fees
• Run recurring audits for revenue leakage, under-billing, margin erosion, missed renewals, and deviations from agreed terms
• Prepare diligence materials for investors and strategic partners, including data room financials, KPI packages, and unit economics
• As-needed fundraising support by developing models for use of proceeds, runway, dilution and cap table scenarios, valuation sensitivities, and more
• Model prospective enterprise and white-label partner deals before signing: Margin waterfall from wholesale cost through merchant margin to the reward percentage funded back to members
• Revenue share and fee structures, minimums, implementation costs, and partner-specific rewards funding
• Points issuance and redemption assumptions, including breakage and the cost of points liability
• Cash timing between supplier payment, member or partner payment, and partner settlement
• Working capital and inventory commitment exposure on pre-booked or pre-purchased inventory
• Run base, upside, and downside scenarios to support go/no-go decisions on large or non-standard deals
• Support 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 billing
• Reconcile transaction, points, and payments data across the platform, payment processors, suppliers, and the general ledger
• Set approval thresholds and controls for discounts, credits, refunds, and non-standard terms
• Align contract templates with what finance can operationally bill, reconcile, and collect
• Oversee 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 sales
• Loyalty points and rewards liability, breakage, and deferred revenue
• Inventory prepayments and supplier deposits
• Lead accounting integration of the M&A activity: purchase accounting, entity consolidation, chart of accounts and systems alignment, and intercompany treatment
• Review and approve monthly financials and deliver management reporting with variance analysis
• Manage 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 compliance
• Oversee payroll, expense management, and benefits accounting in coordination with HR
• Strengthen internal controls and documentation, including readiness for enterprise partner security and vendor reviews
• Manage cash flow forecasting and working capital, including supplier payment timing and inventory exposure
• Define 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 runway

Requirements

What We’re Looking For

• 10+ years of progressive finance experience, including prior CFO, VP Finance, or Controller leadership.
• Demonstrated experience building fundraising models and supporting equity or debt raises
• Strong command of revenue recognition (including principal vs. agent analysis), contract-driven billing, and accounting operations
• Advanced financial modeling skills; FP&A tool experience a plus
• Experience with modern accounting, billing, and payments systems (e.g., QuickBooks, Stripe, Bill.com)
• Experience with M&A integration, including purchase accounting and consolidation
• Comfort working with founders, investors, enterprise partners, and outside counsel
• Ability to work independently in a part-time, high-autonomy role.
• Preferred
• Experience in loyalty and rewards, travel or ticketing marketplaces, fintech, or B2B2C platforms
• Experience accounting for points, gift cards, or other stored-value liabilities
• Experience with enterprise partnerships involving banks, card issuers, or large consumer brands
• CPA, CFA, or MBA
• Experience with growth-stage companies (Series A through C)