Senior Manager, Enterprise Account Executives

Checkout.com • San Francisco, CA

2d • Hybrid

About The Position

Checkout.com is seeking a senior individual contributor to lead pursuits into its largest and most complex global enterprises. The role owns a curated portfolio of strategic targets, such as Fortune 50 and global tier-one accounts, and focuses on high-stakes, multi-year deal campaigns rather than high-velocity sales across a broad territory. Deal cycles may span quarters or years, with contract values involving tens of millions in revenue and billions in processed volume.

The successful candidate acts as the CEO of each pursuit, coordinating cross-functional teams across Solutions Engineering, Product, Treasury, Legal, Regulatory, and Executive Leadership to design bespoke, mission-critical infrastructure solutions for sophisticated global buyers. The role requires sustained executive relationships, complex commercial and technical deal architecture, and leadership through long procurement, evaluation, and proof-of-concept processes.

Checkout.com describes a fast-moving, global fintech business with 20 offices across six continents and London as its headquarters. The company offers a hybrid working model with three days per week in the office.

Requirements

• Substantial history of quota attainment in enterprise software, fintech, or payments, including multi-million-dollar ACV or platform-scale commercial contracts.
• Demonstrated ability to originate, navigate, and close 12- to 24-plus-month enterprise procurement cycles with Fortune 100 or global top-tier digital enterprises.
• Ability to command a room with C-level stakeholders, corporate treasurers, and technical architects, and translate complex payment infrastructure into clear business outcomes.
• Exceptional ability to align internal executive stakeholders, prioritize cross-functional resources, and influence product roadmaps.
• High intellectual curiosity, strategic patience, and structured account-planning skills, using MEDDPICC, Challenger, or equivalent enterprise methodologies.

Nice To Haves

• Prior experience in enterprise payments, financial infrastructure, cloud platforms, or complex transaction processing.

Responsibilities

• Develop and execute comprehensive, multi-year account penetration strategies for a select list of mega-cap enterprises.
• Map complex, matrixed global organizations to identify systemic inefficiencies in existing payment stacks.
• Build sustained relationships across enterprise buying centers, including C-suite executives, global treasury leaders, CTOs, product leaders, and enterprise procurement.
• Mobilize, lead, and coordinate cross-functional pursuit teams to deliver proposals, deep-dive workshops, and executive briefings.
• Translate complex technical, regulatory, and financial mechanics into quantified ROI models and long-term business cases for board-level evaluation.
• Maintain deal momentum and governance through 12- to 24-plus-month procurement, evaluation, and proof-of-concept cycles, including milestone progression and executive alignment.
• Lead master services agreement negotiations, complex pricing frameworks, service-level commitments, and risk and regulatory alignments in coordination with corporate legal and procurement teams.

Benefits

• Hybrid working model with flexibility and three days per week in the office.
• Real ownership, fewer blockers, and meaningful work from day one.
• A work environment intended to support high performers and recognize the impact they deliver.
• Accessible application and work-environment accommodations upon request.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed