Enterprise Sales Leader (US-based, remote)

Booking Holdings Inc.

Job Overview

Location

Remote - US

Job Type

Full-time

Full Job Description

📋 Description

• Own and grow a portfolio of strategic enterprise accounts across the United States as an individual contributor for KAYAK for Business, Booking Holdings’ corporate travel management solution.
• Manage the full enterprise sales cycle from prospecting and lead qualification through product demonstrations, commercial negotiation, contract close, and post-sale onboarding coordination.
• Develop and execute targeted account strategies and executive engagement plans tailored to key decision-makers including Travel Managers, Procurement, Finance, and IT stakeholders.
• Collaborate cross-functionally with Product, Marketing, and Customer Success teams to customize proposals, pricing models, and onboarding experiences for large enterprise customers.
• Maintain accurate, real-time forecasting and pipeline reporting using Salesforce, ensuring visibility into deal progression and revenue expectations.
• Represent KAYAK for Business at industry events, conferences, and executive-level briefings to build brand awareness and credibility in the corporate travel market.
• Monitor competitor activity and evolving market trends in enterprise travel management software, providing actionable insights to Product and Commercial teams to inform roadmap and positioning.
• Navigate complex procurement processes and multi-stakeholder approval workflows to close high-value, multi-year contracts with large organizations.
• Identify and qualify new enterprise prospects through targeted outreach, referrals, and alignment with lead generation and RFP management teams.
• Deliver compelling product demos that highlight KAYAK for Business’s capabilities in compliance, cost savings, and user experience improvements for corporate travel programs.
• Balance autonomous execution with collaborative team alignment in a fast-paced, remote-first environment while maintaining high standards for accuracy and accountability.
• Travel occasionally to meet with clients, attend industry events, or participate in company-wide gatherings to strengthen relationships and reinforce team alignment.
• Ensure all customer interactions reflect KAYAK’s mission to simplify and improve corporate travel through innovation in content, UX, and data-driven insights.
• Contribute to the evolution of KAYAK for Business’s go-to-market strategy by sharing frontline feedback from enterprise customers on product gaps, pricing sensitivity, and feature demand.
• Maintain compliance with internal sales protocols, data hygiene standards, and CRM best practices to support accurate reporting and organizational scaling.
• Build and sustain long-term relationships with enterprise clients by positioning KAYAK for Business as a strategic partner in their travel program transformation.
• Stay informed on regulatory changes and corporate travel policy trends impacting enterprise procurement and compliance needs in the U.S.
• Proactively identify upsell and expansion opportunities within existing enterprise accounts to drive revenue growth and customer retention.
• Partner with Customer Success to ensure seamless handoff and early adoption success after contract execution.
• Align sales activities with broader Booking Holdings initiatives to leverage synergies across KAYAK, momondo, Cheapflights, and HotelsCombined brands.

🎯 Requirements

• 8+ years selling enterprise travel solutions or SaaS travel management software in the U.S. as an individual contributor with a proven track record of closing large, complex deals.
• Proven ability to manage long sales cycles, negotiate multi-stakeholder contracts, and close deals against formal procurement processes.
• Strong executive presence and experience engaging with C-level and senior-level buyers including Travel Managers, Procurement, Finance, and IT leaders.
• Data-driven approach to pipeline management and forecasting with demonstrated proficiency in Salesforce.
• Excellent cross-functional collaboration skills and ability to operate autonomously in a fast-paced, remote environment.
• Willingness and ability to travel occasionally for customer meetings and company events.

🏖️ Benefits

• Work from (almost) anywhere for up to 20 days per year.
• Company-paid therapy sessions through SpringHealth and company-paid Headspace subscription for mental well-being.
• Company-wide week off annually with no work expectations.
• No meeting Fridays to protect deep work time.
• Generous paid vacation, paid birthday off, paid parental leave, and paid volunteer time.
• Development Dollars and leadership development programs with access to thousands of on-demand e-learnings.
• Travel discounts for employees.
• Employee Resource Groups for community and inclusion support.

Skills & Technologies

Senior

Remote

$140k-165k

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Booking Holdings Inc.

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About Booking Holdings Inc.

Kayak is a travel search engine and booking platform that aggregates fares and rates for flights, hotels, rental cars, and vacation packages from hundreds of travel sites and suppliers. It provides price comparison tools, price alerts, mobile apps, and itinerary management features to help consumers find and organize travel options efficiently. The company operates globally and is headquartered in Stamford, Connecticut.

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