VP, Enterprise Sales (Crypto Clients) - Bookit.com

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

Bookit is hiring an Enterprise Sales Director (Crypto & Fintech) to drive adoption of our rewards, travel, and experiences software-as-a-service (Saas) platform across crypto and fintech enterprises. In this role, you will identify and lead business-to-business (B2B) sales with technology-centric enterprise partners including: crypto communities, crypto exchanges, crypto wallets, and fintech platforms, working with them to design and launch customer rewards programs powered by Bookit.

Compensation is tied to performance against revenue plan. You will own the full sales cycle from lead generation and negotiation through contract execution, and remain involved post-close to support successful partner launches and long-term growth. In so doing, you will collaborate cross-functionally with our Customer Success, Legal, Product, and Technology teams to bring enterprise partnerships to life and help grow Bookit's market share.

Responsibilities:

• Source, qualify, and close enterprise B2B deals with crypto and fintech companies against an assigned sales quota
• Own revenue outcomes, managing the full enterprise sales cycle from prospecting through contract execution
• Drive pipeline development, forecasting, and consistent progress toward quarterly and annual targets
• Lead complex enterprise deal strategy, including solution positioning, pricing, and commercial negotiations
• Engage executive stakeholders at prospect companies to secure buy-in and close high-value contracts
• Partner cross-functionally with Product, Engineering, Legal, and Finance to support deal execution and launches
• Represent Bookit as a trusted commercial advisor in crypto, fintech, and payments sales conversations
• Provide accurate pipeline reporting and deal updates to leadership

Requirements

• 7+ years of experience; minimum 3 years leadership in B2B enterprise sales in SaaS and/or travel industries
• Deep familiarity with the crypto and fintech ecosystem (e.g., exchanges, wallets, payments, stablecoins)
• Demonstrated history of closing complex B2B deals in growing companies or startup environments
• Experience selling platforms, marketplaces, or infrastructure-style solutions
• Strong consultative selling, negotiation, and executive communication skills
• Demonstrated executive presence, including the ability to deliver clear, compelling presentations to senior leaders
• Ability to operate effectively in ambiguous, fast-moving environments
• "Player-coach mindset with interest in helping shape early GTM processes
• Experience with white-label platforms, loyalty, rewards, or payments products a plus

Location & Compensation

• Hybrid role in Miami is preferred (remote considered for highly qualified candidates)
• Base salary: $125,000
• Additional compensation: performance-based commission tied to achievement of assigned revenue targets, bringing on-target earnings (OTE) to approximately $250,000

Benefits

• Health care plan (Medical, Dental & Vision)

• Vacation: Flexible/Unlimited PTO with manager approval.

• 401K Plan – Tax-Deferred and/or Roth options

• Collaborative culture with industry veterans and mission-driven builders

Bookit is an equal opportunity employer. 

We strive to create and maintain an equitable workplace where contributors of all backgrounds feel welcomed and valued. We do not discriminate against applicants or employees based on racial identity, color, religion, sex (including gender identity, sexual orientation, and pregnancy), national origin, age, disability or genetic information. Be part of an inclusive company culture emphasizing autonomy, mastery, and purpose.