About Us:

Trail is the context layer AI agents run on. We're building the missing layer between your company's rules, exceptions, and institutional knowledge and the agents trying to act on them. It's a governed graph that lets any agent or platform, including Trail agents, make the right call on your most complex business processes. Agents today fail not because models are weak, but because they're never given the judgment a business builds up over years. We're fixing that.

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The role

Trail is hiring a Strategic Account Executive to win and grow Fortune 1000 accounts. You’ll own complex enterprise sales cycles and close platform deals ranging from $250,000 to $2 million or more in annual contract value.

This is a quota-carrying role for someone who can build executive relationships, develop a clear business case and bring multiple decision-makers to agreement. You’ll work directly with Trail’s founders and leadership team, alongside Solutions Engineering, to help customers adopt AI-powered automation across their organizations.

Roles and Responsibilities

• Own strategic enterprise opportunities through discovery, technical validation, procurement, negotiation and close, with sales cycles typically lasting 6 to 9 months.

• Build relationships with C-suite executives, VPs and senior decision-makers across IT, Operations, Finance and business units.

• Understand each customer’s priorities, identify high-value use cases and connect Trail’s capabilities to a credible business case.

• Build consensus across business sponsors, technical teams, security, procurement and other stakeholders involved in the buying decision.

• Lead account planning and develop opportunities to expand Trail across existing Fortune 1000 customers.

• Partner with Solutions Engineering on enterprise architecture, integrations and technical validation.

• Navigate security reviews, compliance requirements and complex procurement processes while keeping the customer’s decision criteria and next steps in focus.

Requirements and Skills

• At least 5 years of professional experience, including 2 years in a closing or consulting role.

• Experience managing multiple stakeholders and leading conversations with C-level executives and VPs.

• Ability to quickly understand a business, identify a prospect’s challenges and translate them into opportunities for AI.

• Personable and perceptive, with the ability to read the room and build strong relationships.

• Ability to navigate complex organizations, identify decision-makers and develop long-term customer relationships.

Nice to have

• Experience selling at an early-stage startup scaling from 1 to 10+

• Experience in consulting or investment banking.

• Ability to hold basic technical conversations with customers and internal teams.

Additional Information

This is a Bay Area-based hybrid role, with two days per week in our Palo Alto office.

On-target earnings: $300,000 -$400,000 annually, with a 50/50 base-to-commission split.

Base salary: $150,000 - $200,000 annually.

Base salary will be levelled depending on experience and performance during interviews.