Seeking a driven, high-performance closer ready to grow with an early-stage team and help build the revenue engine from the ground up for the future operating system for freight sales. We are looking for a founding sales representative who wants to help shape the revenue engine from day one. This is a commission-only role where the individual will own the entire front end of revenue, encompassing Prospecting, Outreach, Discovery, Demos, and Closing. You will collaborate directly with the founders to refine critical elements such as messaging, ICP targeting, pricing, objection handling, and sales playbooks. This is an opportunity to not just plug into an existing system, but to actively help build the entire sales structure.
Key responsibilities include generating a consistent pipeline through proactive outbound efforts (email, LinkedIn, calls) and effective inbound follow-up. You will be responsible for running detailed discovery calls to qualify prospects based on pain, budget, authority, and urgency, conducting compelling product demos, and successfully moving deals through a simple pipeline structure. The role demands careful activity tracking, maintaining pristine data hygiene, and continuously testing and iterating sales messaging and sequences. The compensation for this role is commission-only, featuring a clear written commission agreement provided before starting, accelerator opportunities for high early performance, and a defined pathway to transition to a base salary plus commission structure after achieving crucial revenue milestones. This position is best suited for a candidate comfortable trading short-term financial certainty for significant long-term upside and organizational influence.
Key Requirements
Based in the U.S. (Central Time preferred)
Reliable internet and video-call capability for remote work
Familiarity with CRM tools and outbound sales workflows
Legally eligible to work as an independent contractor
Ability to generate pipeline through proactive outbound efforts (email, LinkedIn, calls) and inbound follow-up
Proven skill in running detailed discovery calls and qualifying prospects (pain, budget, authority, urgency)
Proficiency in conducting product demos and moving deals efficiently through the sales pipeline
Experience tracking sales activity meticulously and maintaining high data hygiene standards
Capacity to test and iterate messaging and sequences for improved conversion
Comfortable in an early-stage, high-influence environment, trading short-term certainty for long-term upside