Founding Account Executive

Our client is building the AI command center for fleet operations, helping trucking carriers automate the repetitive communications, workflows, and operational tasks that traditionally require large back-office teams. Their AI-native platform integrates across transportation management systems, telematics, safety tools, dispatch software, and other critical systems to automate high-volume operational work.

Already deployed with some of the largest fleets in the United States, the platform is autonomously handling a significant portion of day-to-day workflows while delivering measurable operational improvements. Founded by former engineers and operators from leading fleet technology companies, the business is backed by top-tier investors and is rapidly scaling its go-to-market team.

We are seeking a Founding Account Executive to work directly alongside the founders to build and scale the company’s sales motion from the ground up. This is a high-impact opportunity for a top-performing SaaS seller who enjoys creating process, closing complex deals, and helping shape the future of a fast-growing AI company.

Key Responsibilities:

• Own the full sales cycle from outbound prospecting through discovery, demonstrations, trial management, negotiation, and close.
• Build and develop pipeline through proactive outreach to trucking carriers and transportation operators.
• Partner directly with founders to refine messaging, qualification frameworks, pricing strategies, and overall sales methodology.
• Manage customer evaluation and trial processes, ensuring prospects achieve clear business value and progress efficiently toward purchase decisions.
• Build and maintain forecasting, pipeline reporting, and sales process infrastructure.
• Develop relationships with executive and operational stakeholders across target accounts.
• Represent the company at customer meetings, industry conferences, and transportation-focused events.
• Provide market feedback and customer insights to help influence product direction and go-to-market strategy.

Key Qualifications:

• 3-6+ years of experience closing mid-market or enterprise SaaS deals with contract values of $100K+ ARR.
• Proven full-cycle account executive experience, including prospecting, pipeline generation, and closing complex opportunities.
• Previous experience as a founding AE or early sales hire in a startup environment is highly preferred.
• Demonstrated history of quota attainment with clear performance metrics and achievements.
• Experience selling into logistics, transportation, trucking, supply chain, or operations-focused industries is strongly preferred.
• Track record of rapid career progression and high performance within sales organizations.
• Experience selling complex technical products, including SaaS, AI, machine learning, or enterprise software platforms.
• Strong understanding of pricing strategies, deal economics, contract negotiations, and enterprise procurement processes.
• Proficiency with CRM platforms such as Salesforce or HubSpot.
• President’s Club recognition, top-performer awards, or equivalent sales achievements are highly valued.
• Comfortable working onsite five days per week in San Francisco.