Account Executive - Enterprise

About the role: 

This role is based in Flexport’s new Dublin office and is one of the first Account Executive positions on the ground in Ireland. As part of the founding commercial team, you have the opportunity to build a completely new territory within Flexport — shaping the go-to-market approach, establishing the first enterprise relationships, and helping define how Flexport operates and wins in the Irish market from the ground up.

You will be responsible for driving complex, high-value enterprise deals and establishing long-term strategic partnerships with large customers. This role owns advanced, multi-stakeholder sales cycles that often span regions, business units, and decision layers.

You will be operating with a high degree of autonomy, shaping deal strategy, influencing executive stakeholders, and orchestrating cross-functional teams to deliver differentiated, value-driven solutions.

Pipeline & Opportunity Ownership

• Own and close high-value, complex enterprise opportunities, consistently meeting or exceeding individual quotas.
• Build a strategic pipeline through self-prospecting, account planning, and SDR partnership.
• Proactively identify whitespace, expansion potential, and multi-entity opportunities within target accounts.
• Maintain forecasting, opportunity hygiene, and deal governance in Salesforce (SFDC).

Strategic Discovery & Solution Architecture

• Lead executive-level discovery to understand enterprise supply chain strategy, risk posture, and long-term business objectives.
• Navigate complex buying groups across procurement, ops, finance, IT, and senior leadership.
• Design integrated, multi-product Flexport solutions aligned to customer priorities and business outcomes.
• Position Flexport as a strategic partner through compelling value narratives, business cases, and solution roadmaps.

Deal Strategy, Negotiation & Closing

• Own end-to-end deal strategy for complex opportunities, including stakeholder mapping, decision criteria, and close plans.
• Lead advanced commercial negotiation, pricing, contracts, and non-standard deal structures.
• Orchestrate internal stakeholders (Ops, Finance, Legal, Product) to progress deals efficiently

Onboarding, Expansion & Relationship Leadership

• Own the onboarding motion, ensuring enterprise customers are set up for scalable success.
• Establish and maintain trusted relationships with senior and executive customer stakeholders.
• Identify expansion opportunities together with Account Management to drive sustained growth.
• Serve as a point of escalation and strategic advisor during the customer lifecycle.

Enterprise Leadership & Market Impact

• Act as a senior commercial voice in enterprise pursuits, sharing market insight and customer feedback internally.
• Contribute to enterprise sales best practices, deal reviews, and peer coaching.
• Represent Flexport with credibility and confidence in high-stakes customer interactions.
• As part of the founding Irish team, help shape early market strategy and commercial playbooks that will define Flexport’s approach to the territory going forward.

Prerequisites

• 5+ years of experience managing complex, enterprise-level sales cycles with consistent quota attainment.
• Proven ability to close large, multi-stakeholder deals with long sales cycles and high deal complexity.
• Strong executive presence with the ability to influence senior decision-makers.
• Advanced discovery, negotiation, and value-based selling skills.
• High degree of autonomy, strategic thinking, and commercial judgment.
• Strong logistics, freight forwarding, or supply chain industry experience preferred.
• Self-sufficient learner with a track record of ramping quickly in new markets, products, or environments without an established playbook to follow.
• High level of intellectual curiosity — proactively seeks out market, product, and customer knowledge rather than waiting for it to be provided.
• Deep understanding of the Irish market and local business landscape, with the credibility to engage enterprise buyers from day one.
• Strong mix of supply chain/logistics industry knowledge and tech sales acumen, able to sell a platform-based solution with the same confidence as a traditional freight service.
• High degree of agility and adaptability — comfortable operating with ambiguity and evolving priorities as the Irish territory is built out.
• Fluent in English; additional languages are a plus.

What we offer: 

• An opportunity to contribute to one of the fastest-growing companies, where you’ll have the chance to create a global impact while being a part of a  thriving multinational environment 
• Equity program: every team member becomes a shareholder, aligning our success with yours. As a private company in a multi-trillion dollar industry, you have a direct stake in our collective growth and success.
• Employee Assistance Program through Aetna Resources for Living: Flexport provides an employer-sponsored program at no cost to you and your household members
• Parental leave benefit: Flexport is here to support you and your families in one of the most important times in life – the birth of a child! Our parental leave program allows both mothers and partners to take time off from work for pregnancy, childbirth, and to bond with your new child.

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