Apply

Ready to go for it?

AI Apply speeds things up—apply directly if you prefer.

FREE ACCESS
5,000–10,000 jobs/day
Scoutfield Logo

See all jobs on Scoutfield

Search thousands of fresh jobs every day.

Discover
  • Fresh listings
  • Fast filters
  • No subscription required
Create a free account and start exploring right away.
Trail

Strategic Account Executive

Trail

. Win and grow Fortune 1000 accounts .

Posted 11/6/2026full-timePalo Alto • California • United StatesMid-LevelSenior💰 $150,000 - $200,000 per yearWebsite

Core Competencies

Role fit
Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in managing complex enterprise sales cycles, building relationships with C-suite executives, and navigating procurement processes. Proven ability to identify customer challenges and translate them into AI-driven opportunities while leading account planning and expansion efforts.

Highest-signal resume keywords
Enterprise Sales ManagementC-Level Relationship BuildingComplex Procurement NavigationAccount Planning and ExpansionStakeholder Management

ATS Keywords

Tailor your resume
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Soft Skills
Relationship BuildingCommunicationNegotiationConsensus BuildingProblem Solving
Industry Keywords
Fortune 1000 AccountsTechnical ValidationAI-Powered AutomationSecurity ReviewsConsultingInvestment Banking

About the role

Key responsibilities & impact
  • Win and grow Fortune 1000 accounts
  • Own complex enterprise sales cycles from discovery through technical validation, procurement, negotiation and close
  • Close platform deals ranging from $250,000 to $2 million or more in annual contract value
  • Build relationships with C-suite executives, VPs and senior decision-makers across IT, Operations, Finance and business units
  • Understand customer 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
  • Lead account planning and develop expansion opportunities 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
  • Work directly with Trail’s founders and leadership team to help customers adopt AI-powered automation

Requirements

What you’ll need
  • 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
  • Ability to read the room and build strong relationships
  • Ability to navigate complex organizations, identify decision-makers and develop long-term customer relationships
  • Experience selling at an early-stage startup scaling from 1 to 10+ (nice to have)
  • Experience in consulting or investment banking (nice to have)
  • Ability to hold basic technical conversations with customers and internal teams (nice to have)

Benefits

Comp & perks
  • Commission opportunity through a 50/50 base-to-commission split
  • On-target earnings of $300,000–$400,000 annually
  • Opportunity to work directly with Trail’s founders and leadership team
  • Hybrid work arrangement with two days per week in the Palo Alto office