Head of Operations (Travel Tech / B2B2C Platform) - Bookit.com

Superlogic • Boston, MA

10d • $175,000 - $190,000 • Hybrid

About The Position

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.

Requirements

• 8+ years of operations leadership experience in high-growth technology, marketplace, or platform-based businesses (travel, e-commerce, fintech)
• 5+ years in senior leadership roles (Director, Head, or VP level) with P&L ownership
• Experience partnering closely with executive leadership as an operational decision-maker
• Proven success scaling multi-sided marketplaces with complex inventory management
• Strong vendor and partner management experience at scale
• Track record with major online travel or marketplace platforms (e.g., Expedia, Booking.com), digital booking businesses, or high-growth tech startups
• Proficiency with modern operations tech stacks, CRM systems, BI tools, and AI-driven tools
• Proven ability to lead and scale cross-functional operations teams in fast-growing organizations
• Highly collaborative and adaptable leader who contributes positively to company culture

Nice To Haves

• Spanish proficiency
• Web3 / crypto familiarity
• Miami-based or willing to relocate (preferred, not required)

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.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed
• Number of Employees: 11-50 employees