Enterprise Sales Leader

KAYAK, part of Booking Holdings (NASDAQ: BKNG), is a leading travel search engine. With billions of queries across our platforms, we help people find their perfect flight, stay, rental car and vacation package. We’re also transforming business travel with a new corporate travel solution, KAYAK for Business.

As an employee of KAYAK, you will be part of a travel company that operates a portfolio of global metasearch brands including momondo, Cheapflights and HotelsCombined, among others. From start-up to industry leader, innovation is at our core and every employee has an opportunity to make their mark. Our focus is on building the best travel search engine to make it easier for everyone to experience the world.

We’re fixing the key issues in the travel management sector — content, UX and data — and it’s exciting to see how we deliver compliance and savings to travel programs. This role gives you the chance to bring enterprise customers into that journey.

KAYAK for Business is hiring an Enterprise Sales Leader as an individual contributor to own and grow strategic enterprise accounts across the US. You will be responsible for landing new enterprise customers, managing end‑to‑end sales cycles, negotiating complex contracts, and partnering cross‑functionally to shape product, pricing and go‑to‑market for large customers. A background in SaaS travel management software or enterprise travel management sales is required. This will be a collaborative role, working closely with teams across lead generation, RFP management and marketing!

In this role, you will:

• Own a book of target enterprise accounts and drive new business

• Manage full sales cycle including prospecting, product demos, commercial negotiation and contract close.

• Build account strategies and executive engagement plans (Travel Managers, Procurement, Finance, IT).

• Coordinate internally with Product, Marketing and Customer Success to tailor proposals and onboarding plans.

• Create and maintain accurate forecasting and pipeline reporting for your accounts.

• Represent KAYAK for Business at industry events and run executive‑level meetings and briefings.

• Monitor competitors and market trends; provide feedback to product and commercial teams.

Please apply if you have:

• 8+ years selling enterprise travel solutions or SaaS travel management software in the US as an individual contributor with a track record closing large, complex deals.

• Proven ability to manage long sales cycles, negotiate multi‑stakeholder contracts and close against procurement processes.

• Strong executive presence; comfortable engaging executive buyers and procurement.

• Data‑driven approach to pipeline management and forecasting (Salesforce experience preferred).

• Excellent cross‑functional collaboration skills and ability to operate autonomously in a fast‑paced environment.

• Ability for occasional travel to customer and company meetings.

Benefits & Perks

• Work from (almost) anywhere for up to 20 days per year

• Focus on mental health and well-being:

  • Company-paid therapy sessions through SpringHealth

  • Company-paid subscription to HeadSpace

  • Company-wide week off a year - the whole team fully recharges (and returns without a pile-up of work!)

• No meeting Fridays

• Paid parental leave

• Generous paid vacation + time off for your birthday

• Paid volunteer time

• Focus on your career growth:

  • Development Dollars

  • Leadership development

  • Access to thousands of on-demand e-learnings

• Travel Discounts

• Employee Resource Groups

There are a variety of factors that go into determining a salary range, including but not limited to external market benchmark data, geographic location, and years of experience sought/required. The range for this Massachusetts based role is $140,000 - 165,000.00.

In addition to a competitive base salary, roles are eligible to be considered for additional compensation and benefits including: commission-based compensation; health benefits; flexible spending account; retirement benefits; life insurance; paid time off (including PTO, paid sick leave, medical leave, bereavement leave, floating holidays and paid holidays); and parental leave and benefits.

Inclusion

At KAYAK, we want everyone to have the space to grow, share ideas and do great work. That’s why we’re focused on hiring the best talent from all walks of life and experiences, supporting them well and making sure no one feels like they have to fit a mold to belong here.

Need any adjustments for the interview, application or on the job? No problem - just give us a heads-up. We’ve got you.