Enterprise GTM Lead

About the role

• Trail is the context layer AI agents run on. It is building a governed graph connecting company rules, exceptions, and institutional knowledge with agents, allowing any agent or platform—including Trail agents—to make decisions on complex business processes.
• This is a builder's role working closely with leadership and sales to identify high-potential opportunities, run GTM experiments, and unlock new growth channels.
• Own initiatives end-to-end, from testing customer segments and account-based marketing to exploring untapped channels, and turn successful experiments into repeatable growth engines.
• Trail seeks someone smart, driven, and entrepreneurial who takes initiative, moves fast, and is comfortable working without a playbook. Founder experience is a strong plus.
• Learn more at Trail's website and YouTube.

Responsibilities

• Identify promising customer segments, use cases, and GTM approaches for Trail and its products.
• Design and execute experiments testing new messaging, ideal customer profiles, outreach strategies, and conversion levers.
• Analyze results, identify what works, and iterate rapidly to improve qualified pipeline generation.
• Develop targeted outbound strategies for enterprise accounts across relevant industries.
• Experiment with prospecting approaches, account prioritization, messaging, and outreach tools.
• Work closely with account executives to translate customer conversation insights into more effective prospecting and pipeline generation.
• Identify and test ways to reach enterprise buyers through conferences, events, account-based marketing, partnerships, communities, content-led acquisition, and emerging GTM tools.
• Take new initiatives from idea to execution, measure outcomes, and scale channels demonstrating traction.
• Explore unconventional approaches to reaching decision-makers and generating qualified opportunities.
• Track funnel performance, identify bottlenecks, and use data to make decisions.
• Build lightweight processes and repeatable playbooks around successful experiments.
• Work directly with leadership to bring structure to ambiguous problems and take ownership from strategy through execution.

Requirements

• 5+ years with an undergraduate degree from a Tier 1 institute.
• Founder or early-stage startup experience is strongly preferred: experience building something, taking an idea to market, or creating your own playbook.
• Ability to break down ambiguous problems, identify the highest-impact opportunities, and turn ideas into action.
• Initiative, quick experimentation, and follow-through without waiting for instructions or perfect information.
• Understanding of how businesses buy, what drives customer decisions, and how to translate a product's value into demand.
• Curiosity about new AI and GTM tools and willingness to use them to move faster and work smarter.
• Ability to engage different stakeholders, articulate ideas clearly, and build conviction around new initiatives.