Strategic Enterprise Account Executives

The Role

We are seeking an exceptional Strategic Account Executive to lead our pursuits into the largest and most complex global enterprises. This is a senior Individual Contributor (IC) role designed for an elite enterprise seller who excels at high-stakes, multi-year deal campaigns.

Rather than managing high-velocity pipeline across a wide territory, you will hold deep ownership of a curated portfolio of Checkout’s most strategic targets (e.g., Fortune 50 / global tier-one accounts). Deal cycles on these accounts are transformative, measured in quarters and years rather than weeks, with contract values spanning tens of millions in revenue and billions in processed volume.

You will act as the "CEO of the Pursuit," orchestrating cross-functional deal squads-spanning Solutions Engineering, Product, Treasury, Legal, Regulatory, and Executive Leadership-to architect bespoke, mission-critical infrastructure solutions for sophisticated global buyers.

Key Responsibilities

• Strategic Account Orchestration: Develop and execute comprehensive, multi-year account penetration strategies for a select target list of mega-cap enterprises. Map complex, matrixed global organizations to uncover systemic inefficiencies in their existing payment stacks.
• Multi-Threaded Stakeholder Alignment: Build sustained, credible relationships across diverse buying centers within the enterprise-including C-suite executives, Global Heads of Treasury, Chief Technology Officers, Product Leaders, and Enterprise Procurement.
• Deal Team Leadership (Virtual GM): Mobilize, lead, and coordinate a dedicated cross-functional pursuit team (Solutions Engineers, Product Managers, Legal, Commercial Strategy, Integration Specialists, and C-level sponsors) to deliver high-impact proposals, deep-dive workshops, and executive briefings.
• Complex Commercial & Technical Architecture: Translate complex technical, regulatory, and financial mechanics (e.g., cross-border interchange, scheme routing optimization, local acquiring, unified commerce) into quantifiable ROI models and long-term business cases tailored to board-level evaluation.
• Multi-Year Pursuit Governance: Drive sustained momentum through complex, 12- to 24-plus month procurement, evaluation, and proof-of-concept cycles. Maintain discipline, milestone progression, and executive-level alignment despite organizational shifts, market changes, and competitive pressures.
• High-Stakes Contract Negotiation: Lead master services agreement (MSA) negotiations, complex pricing frameworks, service-level commitments, and risk/regulatory alignments in direct coordination with top-tier corporate legal and procurement teams.

Qualifications & Competencies

• Proven Track Record in Mega-Deals: Substantial history of quota attainment within enterprise software, fintech, or payments, specifically characterized by multi-million-dollar ACV or platform-scale commercial contracts.
• Multi-Year Cycle Mastery: Demonstrated ability to originate, navigate, and close 12- to 24-plus month enterprise procurement cycles with Fortune 100 or global top-tier digital enterprises.
• Executive Gravitas & Technical Acumen: Comfortable commanding the room with C-level stakeholders, corporate treasurers, and technical architects; able to synthesize complex payment infrastructure nuances into clear business outcomes.
• Internal Leadership Without Authority: Exceptional ability to align internal executive stakeholders, prioritize cross-functional resources, and influence product roadmaps to win tier-one logos.
• Strategic Endurance & Analytical Rigor: High intellectual curiosity, strategic patience, and structured account planning skills (e.g., MEDDPICC, Challenger, or equivalent enterprise methodologies).
• Domain Knowledge: Prior experience in enterprise payments, financial infrastructure, cloud platforms, or complex transaction processing is strongly preferred.

• Additional Information
• Bring all of you to work
• We create the conditions for high performers to thrive, through real ownership, fewer blockers, and work that makes a difference from day one.
• Here, you’ll move fast, take on meaningful challenges, and be recognized for the impact you deliver. It’s a place where ambition gets met with opportunity, and where your growth is in your hands.
• We work as one team, and we back each other to succeed. So whatever your background or identity, if you’re ready to grow and make a difference, you’ll be right at home here.
• It’s important we set you up for success and make our process as accessible as possible. So let us know in your application, or tell your recruiter directly, if you need anything to make your experience or working environment more comfortable.
• We understand that work is just one part of your life. Our hybrid working model offers flexibility, with three days per week in the office to support collaboration and connection.
• Curious about what it’s like to be part of our team?