Job Details

Enterprise AI | Account ExecutivePosition Overview

We are seeking a highly skilled Account Executive to join our AI Solutions Sales team. In this role, you will work directly with operators, technical teams, and executive leadership to deploy autonomous AI agents that transform core operational workflows. You will lead complex, consultative sales cycles that require deep discovery, problem mapping, and the ability to navigate large, multi-layered organizations.

You will partner closely with customers to understand their operational challenges, design agent-driven solutions, and guide them through the evaluation and adoption of AI-powered workflows. You will also collaborate with our product and engineering teams to shape how agents are deployed, improved, and expanded across customer environments.

Key Responsibilities

• Own the sales cycle: Run discovery, qualification, multi-threading, scoping, and negotiation end-to-end; build strong executive and operator-level relationships.
• Enterprise discovery: Lead structured workflow mapping across safety, compliance, dispatch, maintenance, and ops; translate fragmented processes into clear automation opportunities.
• Evaluation design: Shape customer evaluations with clear criteria, timelines, success metrics, and stakeholder sequencing; keep cycles predictable and moving forward.
• Value articulation: Build ROI models rooted in workflow time studies, operational KPIs, and risk reduction; present business cases to senior leadership.
• Pipeline leadership: Build, prioritize, and advance a high-quality pipeline across mid-market and enterprise accounts; forecast accurately; maintain disciplined CRM hygiene.
• Discovery excellence: Run structured discovery to surface operational pain, workflow breakdowns, and measurable business impact; separate signal from noise and define clear evaluation paths.
• Strategic qualification: Assess budget, authority, urgency, technical viability, and cross-functional support; identify blockers early and shape deals around true economic buyers.
• Account mapping: Build dynamic account maps identifying champions, influencers, blockers, and executive sponsors; understand internal politics and navigate multi-department complexity.
• Deal strategy: Develop structured opportunity strategies with stakeholder sequencing, mutual success plans, and clear commercial milestones; drive momentum with crisp next-step discipline.
• Agentic framing: Explain autonomous AI agents (task ownership, guardrails, exception handling, memory, auditability) in simple, credible terms for operators and executives.
• Commercial orchestration: Structure proposals, pilots, packaging, and pricing aligned to customer value; support negotiations, SOW drafting, and executive reviews.
• Stakeholder alignment: Multi-thread across Operations, Safety, Compliance, Dispatch, IT, and Finance; ensure all functions are aligned on value, outcomes, and success criteria.
• Expansion motion: Identify new agent opportunities, drive account penetration, and support quarterly executive reviews alongside leadership.

Required Skills & Experience

• 3–5 years of experience as a quota-carrying Account Executive, ideally in SaaS or automation.
• 1–2 years of experience in a startup or fast-moving environment, with comfort operating amid evolving processes and limited structure.
• Proven ability to run complex, multi-threaded sales cycles involving multiple stakeholders and departments.
• Exceptional discovery skills — ability to uncover operational pain, map workflows, and identify high-impact automation opportunities.
• Demonstrated ability to create urgency, drive next steps, and maintain momentum through long enterprise cycles.
• Excellent communication skills with the ability to explain complex concepts simply for operators, frontline managers, and executives.
• Experience with strategic account planning, account mapping, and stakeholder alignment.
• Ability to learn new industries quickly and speak credibly with operational teams in safety, compliance, maintenance, dispatch, or adjacent functions.
• High ownership, self-direction, and comfort leading opportunities independently.

Preferred Qualifications

• Experience selling AI, automation, RPA, or workflow orchestration platforms.
• Familiarity with trucking and logistics systems such as McLeod, Samsara, Tenstreet, RMIS, Highway, or Workday (not required; ability to learn quickly is more important).
• Ability to use time studies, operational KPIs, and risk reduction metrics to quantify ROI.
• Experience navigating internal politics, aligning cross-department teams, and multi-threading across complex organizations.
• Comfort addressing questions around agent accuracy, escalation paths, and operational safeguards.

What You'll Bring

• High ownership and the ability to steer customers through evolving, unstructured processes.
• Curiosity for how operational teams work and where agents can take full task ownership.
• Ability to manage change thoughtfully and help teams adopt agent-driven workflows.
• Strong commercial instincts and the ability to translate operational pain into clear business cases.
• A collaborative approach and eagerness to work closely with founders and engineers.

What We Offer

• The opportunity to shape the commercial strategy for a new category of AI-driven operations.
• Direct collaboration with founders and engineering as you influence the agent roadmap.
• Competitive compensation including base salary, commission, and equity.
• A fast-moving, collaborative environment where customer feedback drives product evolution.