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Trail

Digital operations platform for hospitality checklists

Enterprise Account Executive

Account ExecutiveConfirmed live in the last 24 hours
Full-timePalo Alto, CA, USA

About the Job

Requirements

  • Five years of closing experience, including at least two years of enterprise experience.
  • A proven track record closing deals of $250,000 or more in Fortune 1000 environments.
  • Experience with complex enterprise sales cycles of at least six months, procurement processes, and security and compliance requirements.
  • Strong relationships with enterprise IT and business stakeholders.
  • Ability to navigate matrix organizations and build consensus among multiple decision-makers.
  • Track record of growing accounts through expansion and strategic relationship building.
  • Enterprise credibility and comfort presenting to C-suite and board-level audiences.

Responsibilities

  • Own and close seven-figure deals with Fortune 1000 organizations in a quota-carrying role.
  • Manage complex enterprise sales cycles, multiple C-level stakeholders, and strategic platform deployments.
  • Build relationships with C-suite executives, vice presidents, and senior enterprise decision-makers.
  • Navigate complex procurement processes, security reviews, and enterprise compliance requirements.
  • Build consensus among stakeholders across IT, Operations, Finance, and business units.
  • Plan strategically for accounts and expand existing Fortune 1000 customer relationships.
  • Partner with Solutions Engineering on enterprise architecture and technical validation.
  • Partner directly with the founders and executive team to establish the company as an enterprise standard for AI-powered automation and work with customers on initiatives affecting thousands of users and millions in operational savings.

Desired Qualifications

  • Experience selling AI or machine-learning platforms, automation tools, or enterprise software as a service.
  • Background in document-heavy industries such as Finance, Healthcare, or Supply Chain.
  • History working at high-growth enterprise software companies with more than $100 million in annual recurring revenue.
  • Technical aptitude to understand platform capabilities and enterprise integration requirements.

About the Company

Trail

Digital operations platform for hospitality checklists

Trail provides a digital operations platform for hospitality to replace paper-based processes, centered on a smart checklist that guides daily tasks like food safety and opening/closing checks. It works by prompting the right team member at the right time, logging every completed action to support accountability, audits, and inspection readiness, and offering features such as custom tasks, record logs, audits, dashboards, corrective actions, and real-time alerts, plus an AI Copilot for policy questions. It differentiates itself by targeting multi-site hospitality operations with a clear path from paper to digital workflow, comprehensive audit and compliance tools, and scalable pricing based on active sites with unlimited users. Trail aims to boost operational efficiency, consistency, and compliance across hospitality teams by replacing manual paperwork with an integrated, data-driven system.

Company size
Not listed
Company stage
Not listed
Total funding
Not listed
Headquarters
San Francisco, CA
Founded
2026

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