Director of Finance & Sales Innovation, VACAYA

Title: Director of Finance & Sales Innovation, VACAYA

Location: McLean, Virginia USA

Reports to: CEO and CMO

Employment Type: Full-time

About VACAYA

VACAYA is a community-driven travel company focused on curated full-ship and full-resort travel experiences. We prize guest service excellence, data-driven sales growth, and disciplined financial operations that support sustainable expansion.

Role Overview

VACAYA is hiring a hands-on Director of Finance & Sales Innovation to own all financial operations while simultaneously leading our Sales and Guest Service teams to deliver outstanding results. This hybrid role combines full-spectrum small-business finance responsibilities (bookkeeping, payments, payroll oversight, credit card processing, reconciliations, and tax reporting, including the processing of 1099s) with strategic and operational leadership of Sales/Guest Service using RezMagic and ZenDesk. The ideal candidate is detail-oriented with strong accounting chops, payment systems experience, and proven sales leadership within travel, hospitality, or consumer/lifestyle brands.

Key Dual Responsibilities

Financial Operations

• Own day-to-day financial operations: bookkeeping, AP/AR, invoicing, bank reconciliations, cash management, and month-end close.
• Manage all incoming and outgoing payments: vendor payments, refunds, guest payments, travel agent commissions (including eligibility to earn commission based on the established criteria), and internal transfers.
• Oversee credit card processing systems and merchant relationships; ensure secure PCI-compliant processing and reconciliation of card transactions.
• Maintain and reconcile merchant accounts, payment gateways, and third-party travel platforms.
• Oversee payroll processing or coordinate with payroll provider to ensure timely, accurate payroll and related tax filings.
• Oversee VACAYA’s Healthcare and 401K initiatives for all employees.
• Prepare and deliver accurate monthly financial statements, cash flow forecasts, and variance analysis to senior leadership.
• Manage accounts receivable collections and traveler payment plans; resolve disputed charges and chargebacks.
• Prepare P&L Statements for each VACAYA event.
• Administer 1099 preparation and filing; coordinate with external accountants for year-end tax reporting, corporate tax filings, and audit support.
• Implement and maintain internal financial controls, policies, and documentation to safeguard assets and ensure compliance.
• Manage relationships with bank(s), insurers, payroll/benefits vendors, external accountants, tax advisors, and individual states where Seller of Travel licenses and bonds are required.
• Lead budgeting and forecasting processes; provide scenario analyses to inform pricing, promotions, and new product investments.
• Maintain general ledger integrity, chart of accounts, and financial process improvements; supervise any bookkeeping staff or contractors.
• Ensure compliance with applicable state and federal financial regulations, sales tax obligations, and travel-industry-specific reporting.

Sales & Guest Service Innovation & Leadership

• Develop and execute sales strategies and tactics to meet/exceed revenue targets through outreach to travel agents, partners, and direct guests. Represent company at industry and trade events.
• Lead, coach, and manage Sales and Guest Service teams: hiring, training, scheduling, performance reviews, and issue resolution.
• Own performance metrics and reporting cadence (daily/weekly/monthly Sales Reports); translate data into actionable strategies.
• Manage sales technologies and workflows: RezMagic (ecommerce/reservations), ZenDesk (guest inquiry tracking), Grasshopper or equivalent phone systems, and related tools.
• Monitor frontline interactions: respond to escalated agent/guest issues.
• Actively engages with guests by handling incoming calls and inquiries when needed, ensuring seamless coverage for team members and maintaining a strong connection to guest feedback, needs, and satisfaction.
• Oversee sales audits and data integrity:
• Maintain cruise/resort manifests and guest lists
• Audit reservations, ship inventory, and pricing
• Conduct travel agent commission audits and anti-poaching resolution
• Deliver year-over-year growth in productive Travel Agent ranks.
• Build and maintain strong relationships with top travel agents and partner distribution channels; assign and monitor agent relationships across the team.
• Ensure enforcement and communication of guest and agent policies; draft and maintain policy documents.
• Support onboard/resort Guest Services when attending events/trips.
• Collaborate with Marketing to align promotion strategies, pricing, and campaigns that drive conversions. Deliver requested sales reports to CMO that inform sales & marketing strategies.
• Assist with employee onboarding and team hardware/software provisioning.
• Lead or participate in special projects (new product launches, systems implementations, process re-engineering).
• Oversee the delivery of email lists generated from consumer submissions at marketing events.

Cross-Functional & Strategic

• Serve as a trusted business partner to CEO, CMO, and senior leadership, integrating financial insights with sales strategy.
• Drive cross-functional alignment between finance, sales, marketing, guest experience, and operations.
• Recommend and implement process and systems improvements (automation of payments, reporting dashboards, fraud prevention).
• Ensure data privacy and security best practices for guest financial data.

Requirements

• 5 years combined experience in finance/accounting and sales leadership; or equivalent combination of relevant experience.
• Solid bookkeeping and accounting experience: GL management, reconciliations, month-end, financial statements, payroll coordination, and tax reporting (1099s, year-end).
• Experience with payment processing systems, merchant services, PCI compliance, and chargeback resolution.
• Proven sales leadership experience with measurable success meeting/exceeding targets; prior experience in travel, hospitality, consumer, or lifestyle brands strongly preferred.
• Hands-on experience with RezMagic (or similar reservations/ecommerce platforms) and ZenDesk (or similar guest inquiry/CRM systems); familiarity with call center operations and phone systems (e.g., Grasshopper).
• Strong analytical skills and experience creating and maintaining sales & financial reports and dashboards.
• Excellent communication and interpersonal skills; ability to influence across all levels including executive leadership.
• Highly organized, detail-oriented, with strong problem-solving skills and the ability to prioritize in a fast-paced environment.
• Proficiency with accounting software (e.g., QuickBooks Online, Xero), Excel/Google Sheets, and modern SaaS tools.
• BA/BS degree in Finance, Accounting, Business, or related field preferred; CPA or relevant certification a plus.
• Team player with integrity, accountability, and a collaborative spirit.

Compensation & Benefits

• Competitive salary (commensurate with experience) performance incentives.
• Benefits package (health, paid time off, travel perks, etc.), with details provided during interview process.
• Hybrid work model with required in-office days, work-from-home days, and occasional travel to events/trips.

How to Apply

Please submit a resume, your social handles, and a brief cover letter highlighting relevant finance and sales leadership experience, familiarity with RezMagic and ZenDesk, and a summary of payments/merchant systems you’ve managed to info@myvacaya.com. Subject: Director of Finance & Sales Innovation Position

VACAYA is an equal opportunity employer. We welcome candidates from diverse backgrounds and lived experiences.