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Trail

Trail, a Palo Alto-based company, enables AI agents to leverage enterprise institutional knowledge and business rules, helping Fortune 1000 organizations in finance, healthcare, and supply chain management achieve operational efficiency at scale.

See 16 open roles

Work at Trail?

Locations
Bengaluru+2
Also Palo Alto, Remote
Team size
11-50
Founded 2026
Total raised
$43.6M
Pre-seed
Salary range
$100–400k
+ equity · 6 of 16 roles
Open roles
16

Open positions · 16

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About Trail

Trail is a Palo Alto-based company that equips AI agents with the institutional knowledge, business rules, and exceptions that enterprises have built up over years, addressing the fundamental problem that AI agents fail without this critical judgment. The company serves large enterprises, including Fortune 1000 organizations, primarily in document-heavy industries such as finance, healthcare, and supply chain management. Trail's deployments are strategic platform initiatives that engage IT, Operations, Finance, and Business Unit stakeholders, typically impacting thousands of users and generating millions in operational savings. The company targets enterprises with 1,000+ employees, with deals valued at $100K+ ACV that typically take six months or longer to close. Led by a small but growing sales team under Michael Cattermole's leadership, Trail is expanding its enterprise sales capacity and maintains a hybrid work model from its Palo Alto headquarters.

Culture & values

Small sales team still growing with real influence on enterprise sales motion

AEs work directly with the founders and can bring the CEO onto customer calls

Company values reps who follow a disciplined sales process and can clearly explain why they win or lose deals

Reps sit close to leadership

AEs source about half of their own pipeline through outbound prospecting

Hybrid work arrangement out of Palo Alto office with flexible in-office days

Funding

$43.6Mtotal raised

Company at a glance

Founded2026
Location
Palo Alto, United States
Websitetrails.so
LinkedInLinkedIn

Top Benefits

  • Compensation includes equity aligned with both individual and company success
  • Hybrid work arrangement out of Palo Alto office with flexible in-office days

The team at Trail

11-50 peopleSee everyone on LinkedIn

Location

Life at Trail

Frequently asked questions

Key benefits include: Compensation includes equity aligned with both individual and company success, Hybrid work arrangement out of Palo Alto office with flexible in-office days.

Of 16 open roles, Trail has 3 remote, 10 hybrid, 3 on-site positions.

Trail is based in Palo Alto.

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