Senior Enterprise Account Executive

About the role

The Sr. Enterprise Account Executive will drive strategic sales initiatives targeting merchants with annual U.S. D2C sales exceeding $500M, navigating complex deals with extended sales cycles ranging from six months to one year. In this role, you will build detailed account maps and execute multi-threaded outreach to engage and establish relationships with key stakeholders at the highest levels. Leveraging your expertise in enterprise sales and data-driven insights, you will deliver tailored, ROI-driven solutions that position Zip as the premier payment option for the 100M+ Americans traditionally underserved by legacy financing and payment providers. As a trusted advisor, you will unlock value for merchants by addressing their unique challenges and driving incremental business growth.

Responsibilities

• Account Ownership & Mapping: Manage and map a dynamic roster of 15-20 qualified high-value enterprise accounts, ensuring tailored and strategic engagement.
• Stakeholder Engagement: Conduct highly targeted and customized outreach to develop relationships with 3-5 key stakeholders per account, ensuring comprehensive account coverage.
• Strategic Solution Selling: Develop and present ROI-driven business cases and analyses rooted in pains uncovered during a thorough Discovery process. Leverage account mapping and data insights to quantify and articulate Zip’s value. Engage internal resources to execute multi-threaded sales strategies.
• Pipeline Management: Maintain an active pipeline, qualifying and transitioning opportunities as discovery calls progress.
• Collaboration: Partner closely with marketing, analytics, and engineering teams to customize solutions and support client success.
• Tech Innovation & AI: Regularly experiment with AI driven workflows to refine messaging, surface account opportunities, and unlock smarter, faster decision making across the sales cycle.
• Account Review Process: Participate in weekly 1:1 sessions to review top-of-funnel KPIs and account activity, ensuring strategic alignment.

Requirements

• Enterprise Sales Expertise (12+ years)
• Strong ability to generate and manage a highly detailed and organized pipeline of enterprise sales opportunities.
• Extensive experience engaging C-suite and VP-level decision-makers and managing multi-threaded relationships within large enterprise organizations.
• Expertise in strategic sales methodologies such as MEDDIC, Challenger Sale, or Solution Selling.
• Demonstrated ability to leverage data to build compelling business cases and ROI analyses.
• Expertise in Salesforce, LinkedIn Sales Navigator, and other modern sales platforms.
• Familiarity with a range of e-commerce platforms, orchestration layers, and enterprise software tech stacks.

Qualifications

• Deep understanding of retail payments, BNPL, payment systems, and checkout optimization, with insights into industry challenges and solutions.
• Proven success in enterprise sales, closing complex, multi-stakeholder deals with Fortune 1000 merchants.
• Experience managing and closing large-scale deals (e.g., $1M+ contracts) with major retailers or companies of similar scale.
• Strong ability to generate and manage a highly detailed and organized pipeline of enterprise sales opportunities.
• Extensive experience engaging C-suite and VP-level decision-makers and managing multi-threaded relationships within large enterprise organizations.
• Ability to tailor communication to diverse stakeholders, including Influencers, Coaches, Economic Buyers, and Decision Makers.
• Deep understanding of retail payments, BNPL, payment systems, and checkout optimization, with insights into industry challenges and solutions.
• Expertise in strategic sales methodologies such as MEDDIC, Challenger Sale, or Solution Selling.
• Demonstrated ability to leverage data to build compelling business cases and ROI analyses.
• Expertise in Salesforce, LinkedIn Sales Navigator, and other modern sales platforms.
• Familiarity with a range of e-commerce platforms, orchestration layers, and enterprise software tech stacks.

Skills

• Enterprise Sales Expertise
• Strategic Relationship Management
• Payments Industry Knowledge
• Process Methodology & Data-Driven Selling
• Advanced Sales Tools Proficiency
• Collaboration
• Tech Innovation & AI

Benefits

• Flexible working culture
• Incentive programs
• Unlimited PTO
• Generous paid parental leave
• Leading family support policies
• Company-sponsored 401k match
• Learning and wellness subscription stipend
• Beautiful Union Square office with a casual dress code
• Industry-leading, employer-sponsored insurance for you and your dependents, with several 100% Zip-covered choices available

Pay

The actual base salary will be determined by various individualized factors, including job-related knowledge, skills, experience, location, internal equity, as well as other objective business considerations. The annual base Pay Range for this position is $135,000 - $170,000 USD. In addition, you will be eligible for a commission of equal value to the base pay range, making on-target earnings $270,000 - $320,000 (OTE) (50% base salary and 50% commission).

Schedule

Remote-first opportunity in the United States. Hybrid opportunity for Greater New York Metro based employees at our Manhattan office.

Application Instructions

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