Enterprise GTM Lead

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.

Visit our Website (https://trailhq.com) and Youtube (https://www.youtube.com/watch?v=5nmGmgv9lx0) to learn more!

The role

This is a builder's role. You'll work closely with the leadership and sales teams to identify high-potential opportunities, run GTM experiments and unlock new channels for growth. From testing a new customer segment to experimenting with account-based marketing or exploring an untapped channel, you'll own initiatives end-to-end and turn what works into repeatable growth engines.

We're looking for someone smart, driven, and entrepreneurial — someone who takes initiative, moves fast, and is comfortable figuring things out without a playbook. Founder experience is a strong plus.

What you'll do

1. Run GTM experiments

• Identify promising customer segments, use cases, and GTM approaches for Trail and its products.
• Design and execute experiments to test new messaging, ICPs, outreach strategies, and conversion levers.
• Analyse results, identify what works, and rapidly iterate to improve qualified pipeline generation.

2. Build and scale outbound motions

• Develop targeted outbound strategies for enterprise accounts across relevant industries.
• Experiment with prospecting approaches, account prioritisation, messaging, and outreach tools.
• Work closely with AEs to turn insights from customer conversations into more effective prospecting and pipeline generation.

3. Create new GTM channels

• Identify and test new 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 the channels that demonstrate traction.
• Explore unconventional approaches to reaching decision-makers and generating qualified opportunities.

4. Own outcomes end-to-end

• Track funnel performance, identify bottlenecks, and use data to make decisions.
• Build lightweight processes and repeatable playbooks around successful experiments.
• Work directly with leadership, bringing structure to ambiguous problems and taking ownership from strategy through execution.

Who we're looking for

• 5+ years with an undergraduate degree from a Tier 1 institute
• Founder or early-stage startup experience is strongly preferred. You've built something, taken an idea to market, or worked in an environment where you had to create your own playbook.
• You can break down ambiguous problems, identify the highest-impact opportunities, and turn ideas into action.
• You don't wait for instructions or perfect information. You take initiative, experiment quickly, and follow through.
• You understand how businesses buy, what drives customer decisions, and how to translate a product's value into demand.
• Curious about new AI and GTM tools and willing to use them to move faster and work smarter.
• Can engage with different stakeholders, articulate ideas clearly, and build conviction around new initiatives.