At VACAYA, we’re on an exciting journey to create one of the most innovative travel brands in the world. As we grow, we’ll assemble a fantastic team of individuals who understand the true importance of teamwork.
VACAYA’s core values inform how our business is run day-to-day. We strive to be thoughtful, generous, curious, bold, flexible, gracious, thankful, and above all, to do the right thing… for each other, for our guests, and for our industry partners. All of us here at VACAYA do this work because of the joy that comes from creation and execution. We are always a team – working together to bring VACAYA’s Mission and Vision to life.
OUR MISSION
To fulfill the vacation dreams of all adults who believe “love is love” through our commitment to highly-personalized world-class service, quality experiences, and unmatched value.
OUR VISION
We believe consistent, ethical, and quality interactions with our guests, business partners, employees, and community will result in loyal long-term relationships. VACAYA is committed to helping make the world a better place by inspiring guests to volunteer, donate, and promote human understanding to those less fortunate within the communities we visit around the globe. Our success is measured by guests who choose to return to us again and again, and who encourage their friends and family to experience VACAYA, as well.
At VACAYA, the personality and cultural leanings of each individual team member matter as much as their skills sets. Vacayans are kind, clever, on top of it, able to think ahead, intuitive, passionate, and respected throughout the industry.
Our hope is to partner with people who are equally right (creative) and left brained (logic) – able to bring a magical flair to the VACAYA experience while being acutely mindful of our business.
As positions become available (and they will), please check back here for specific details and submission instructions.
OPEN POSITIONS
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.