Posted Nov 2, 2026

Sales Development Representative (Outbound) - Contractor

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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 and Youtube to learn more!

About the role

The Sales Development Representative role at Trail is a foundational role within our sales  function. As a Sales Development Representative, you will be the tip of the spear, connecting with  prospective customers via outbound activity and uncovering new sales opportunities for our Sales  team. 

You will be on the front lines every day, making cold calls and sending emails, so you must be  comfortable talking to strangers, addressing questions and objections, effectively introducing  prospects to our products and value proposition, and ultimately building our sales pipeline. 

We want to hear from you if you want to be a part of our growth journey!

What you will work on: 

Preferred experience: 

Our Benefits 

Location: Remote

1+ year lead generation or inside sales experience in SaaS; experience with LinkedIn Sales Navigator, Clay, and Apollo; strong communication and objection handling skills.

Key Responsibilities

Skills & Tools

LinkedIn Sales Navigator, Clay, Apollo

Job Details

Benefits

About Trail

A company building the context layer AI agents run on, providing a governed graph for complex business processes. — Industry: Information Technology