Enterprise Sales Leader

KAYAK

Enterprise Sales Leader at KAYAK for Business responsible for managing new enterprise accounts. Leading sales cycles, negotiating contracts, and collaborating with cross-functional teams.

Posted 5/20/2026full-timeCambridge • Massachusetts • 🇺🇸 United StatesSenior💰 $140,000 - $165,000 per yearWebsite

About the role

Key responsibilities & impact

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.

Requirements

What you’ll need

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

Comp & 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

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

sales cycle managementprospectingproduct demoscommercial negotiationcontract closingaccount strategy developmentforecastingpipeline reportingdata-driven decision makingnegotiation of multi-stakeholder contracts

Soft Skills

executive presencecross-functional collaborationautonomous operationengagement with executive buyersadaptability in fast-paced environments