Role Overview

The Sales Manager, Mid-Market & Enterprise leads Trucker Path's team of Senior Account Executives selling into fleets in the 3-100 truck range — the mid-market and enterprise segment of the trucking and logistics market.

This role is responsible for driving strategic alignment and operational excellence across the team, ensuring it hits ambitious sales and growth targets in a segment where deal complexity, sales cycle length, and account value run meaningfully higher than the owner-operator segment. It requires a leader who can coach senior, experienced AEs through longer, multi-stakeholder sales cycles rather than managing a high-volume, transactional motion.

Team Leadership

• Lead and develop a team of Senior Account Executives focused on mid-market and enterprise fleet accounts (3-100 trucks)

• Manage day-to-day operations, accountability, and performance consistency across the team

Strategic Execution

• Design and implement sales strategies tailored to mid-market and enterprise buying cycles — longer timelines, multiple stakeholders, and higher deal value — to accelerate revenue growth in this segment

• Align segment strategy with overall company growth objectives

Performance Optimization

• Track KPIs relevant to this segment — quota attainment, average deal size, sales cycle length, and win rate — and drive continuous improvement across the team

• Analyze performance data to identify where deals are stalling or reps are underperforming, and act on it

Process Improvement

• Identify inefficiencies in the mid-market and enterprise sales motion and implement best practices for workflows, reporting, and resource allocation

• Build repeatable processes for the more complex deal structures common in this segment (custom pricing, multi-stakeholder approval, contract negotiation)

Cross-Functional Collaboration

• Partner with Sales, Marketing, Product, Customer Success, and Finance to ensure seamless execution of mid-market and enterprise deals

• Coordinate with Legal/Finance as needed on contract terms, pricing structures, and enterprise-specific requirements

Compliance & Quality

• Ensure adherence to company policies, industry regulations, and internal operational standards in how enterprise and mid-market deals are structured and closed

Leadership Development

• Mentor and coach Senior Account Executives, fostering accountability, innovation, and high performance at a more sophisticated deal level

• Support career growth and retention of senior, experienced sellers on the team

Reporting & Insights

• Provide regular performance reports and actionable insights to senior leadership on mid-market and enterprise pipeline health and grow

Must Have

• 4-5+ years of experience in sales management or operations leadership, with at least 2 years managing sales teams

• Experience managing complex, higher-value, longer sales-cycle deals — as opposed to high-volume, transactional sales

• Background in trucking, logistics, transportation, or B2B SaaS sales strongly preferred

• Demonstrated ability to lead and develop senior-level individual contributors

• Strong data-driven decision-making skills, with experience using reporting and performance metrics

• Excellent verbal and written communication skills

• Experience with CRM systems, analytics platforms, and operational management tools

Nice to Have

• Experience selling fleet management, telematics, or logistics technology to fleets in the 3-100 truck range

• Experience managing enterprise deal cycles involving procurement, legal, or multi-stakeholder buying committees