Role overview

Checkout.com powers digital payments for over one billion global shoppers annually, working behind the scenes for companies like eBay, Spotify, Klarna, Uber, and Sony. We are seeking a Strategic Enterprise Account Executive to lead pursuits with the world’s largest and most complex global enterprises, taking ownership of a carefully curated portfolio of Fortune 50 and tier-one strategic accounts rather than managing high-volume pipeline across territories.

Key responsibilities

Develop and execute comprehensive multi-year account strategies for mega-cap enterprises, identifying systemic inefficiencies within their existing payment infrastructure.
Build and maintain credible relationships across multiple stakeholder groups within enterprises, including C-suite executives, Global Heads of Treasury, Chief Technology Officers, and corporate procurement teams.
Lead and coordinate dedicated cross-functional pursuit teams spanning Solutions Engineering, Product, Legal, Treasury, Regulatory, and Executive Leadership to deliver tailored proposals and executive-level presentations.
Translate complex technical, regulatory, and financial concepts into quantifiable ROI models and business cases designed for board-level evaluation.
Navigate and drive momentum through extended procurement cycles lasting 12 to 24 months or longer, maintaining alignment through organizational changes and competitive challenges.
Lead negotiations of master services agreements, pricing frameworks, service-level commitments, and risk alignments with top-tier corporate legal and procurement partners.

Requirements

Proven track record of quota attainment in enterprise software, fintech, or payments, with substantial experience closing multi-million-dollar contracts or platform-scale commercial deals.
Demonstrated success originating, navigating, and closing enterprise procurement cycles lasting 12 to 24 months or longer with Fortune 100 or global tier-one digital enterprises.
Executive presence and ability to engage confidently with C-level stakeholders, corporate treasurers, and technical architects while communicating complex payment infrastructure concepts clearly.
Strong capability to align internal executive stakeholders, influence resource allocation, and shape product roadmaps to support winning large enterprise accounts.
Strategic account planning expertise using methodologies such as MEDDPICC, Challenger, or equivalent enterprise sales frameworks.
Prior experience in enterprise payments, financial infrastructure, cloud platforms, or complex transaction processing is strongly preferred.

What makes this role worth considering

This is a senior individual contributor position designed for an elite enterprise seller where you operate with deep ownership of transformative, high-stakes pursuits rather than managing high-velocity pipeline. Deal cycles are measured in quarters and years with contract values spanning tens of millions in revenue, allowing you to orchestrate sophisticated, mission-critical infrastructure solutions for the world’s most ambitious global buyers.