Head of Operations (Travel Tech / B2B2C Platform) - 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

Head of Operations

Location: Miami-Hybrid preferred. Remote considered for highly qualified candidates

Salary Range: $175,000 – $190,000

The Head of Operations drives strategic excellence across all facets of Bookit’s rapidly scaling B2B and B2B2C platform. The role combines deep operational expertise with senior leadership to oversee a digital booking platform spanning travel, VIP experiences, premium retail, and blockchain-powered payments.

You will help grow and support a cross-functional team of technology builders, operators, and customer service professionals, delivering high-value rewards to consumers and meaningful engagement to brand clients. The ideal candidate has experience scaling operations in high-growth travel technology, marketplace, or startup environments, with the strategic and financial acumen to build scalable operating frameworks at the intersection of travel, fintech, loyalty, and entertainment.

**This role is not focused on hotel property operations, on-site hospitality, or traditional guest services. We are seeking operators with experience running technology platforms, marketplaces, and digital booking systems at scale.

We value operators who are comfortable building structure in ambiguity and who thrive in early-stage, fast-scaling platform environments.

Responsibilities

• Develop and execute comprehensive operational strategies that support Bookit’s rapid growth across travel, experiences, retail, and payments verticals
• Own and scale core business operations across Bookit, including people operations, finance operations, legal/compliance workflows, vendor management, and internal systems
• Partner closely with the CEO and executive team to translate company strategy into operational plans, priorities, and execution
• Support the CEO and Executive Team in serving our B2B2C brand clients and developing foundational partnerships across the travel and experiential industries
• Serve as primary liaison between Bookit leadership and its founding partners, ONE Company, Starboard, Superlogic and other affiliated companies
• Collaborate closely with our Product, Technology, Marketing, and Finance teams to optimize the Bookit platform for our brand clients and ensure a seamless end-to-end customer experience for our end users
• Oversee Customer Service team to ensure reliable 24/7 customer support; develop business continuity plans in the event of travel disruptions, or other unforeseen events
• Oversee hiring, company goal setting, and personnel evaluation/development
• Foster a culture of continuous improvement and data-driven decision making; establish and monitor key performance metrics across business units
• Manage budgets, forecasting inputs, and operational spend in partnership with Finance; ensure cost discipline and operational efficiency
• Stay current with industry trends, emerging technologies, and best practices in travel operations, e-commerce fulfillment, and experiential services
• Build, document, and continuously improve scalable processes across onboarding/offboarding, hiring operations, vendor onboarding, contract management, and internal approvals
• Oversee operational readiness for rapid growth, including headcount scaling, cross-functional workflows, and internal tooling
• Execute with minimal oversight, with the ability to navigate complex operational challenges from concept through completion

Requirements

• 8+ years years of operations leadership experience with a proven track record in high-growth online travel, e-commerce, and/or fintech companies
• 5+ years in senior leadership roles (Director, Head, or VP level) with P&L ownership
• Demonstrated success scaling operations in multi-sided marketplace environments with complex inventory management
• Experience building and scaling internal operations, systems, and processes from scratch
• Experience partnering closely with executive leadership as an operational decision-maker
• Proven ability to lead and scale cross-functional operations teams in fast-growing organizations
• Strong vendor and partner management experience at scale
• Proficiency with modern operations tech stacks, CRM systems, BI tools, and AI-driven tools
• Collaborative approach with the ability to work effectively across all organizational levels and be a positive contributor to company culture
• Self-starter with the ability to deliver exceptional customer experiences and thrive as a leader amidst a fast-paced, entrepreneurial environment

Bonus:

• Experience at a major online travel platforms (e.g., Expedia, Booking.com, Marriott), experiential companies, or other scaled consumer marketplaces
• Spanish proficiency
• Familiarity with crypto, fintech, or modern payments ecosystems

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.