Strategic Sales Manager - Mid-Market & Enterprise Fleets

Trucker Path, Inc.; Philippines; On-site; PHP 1,400,000 - 2,200,000; Full time

Job summary

Trucker Path, Inc. is seeking a Sales Manager to lead the Mid-Market & Enterprise Senior Account Executives selling into fleets 3-100 trucks.

You will shape strategy, coach experienced AEs, and ensure the team achieves ambitious revenue targets in a segment with longer cycles and higher deal value. You will collaborate with Sales, Marketing, Product, Customer Success, and Finance to optimize processes and pricing for enterprise deals, while mentoring the team toward higher performance and

Qualifications

• 4-5+ years of experience in sales management or operations leadership
• Experience managing complex, higher-value, longer sales-cycle deals
• 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

Responsibilities

• Lead and develop a team of Senior Account Executives focused on mid-market and enterprise fleet accounts (3-100 trucks)
• Design and implement sales strategies tailored to mid-market and enterprise buying cycles - longer timelines, multiple stakeholders, and higher deal value
• Track KPIs relevant to this segment - quota attainment, average deal size, sales cycle length, and win rate
• Identify inefficiencies in the sales motion and implement best practices for workflows, reporting, and resource allocation
• Partner with Sales, Marketing, Product, Customer Success, and Finance to ensure seamless execution of mid-market and enterprise deals
• Coordinate with Legal/Finance on contract terms, pricing structures, and enterprise-specific requirements
• Mentor and coach Senior Account Executives, fostering accountability, innovation, and high performance
• Provide regular performance reports and actionable insights to senior leadership on mid-market and enterprise pipeline health

Skills

Leadership

Data-driven

CRM/Analytics

Cross-functional

Strategic planning

Tools

Salesforce

HubSpot

Tableau

Job description

Trucker Path, Inc. is seeking a Sales Manager to lead the Mid-Market & Enterprise Senior Account Executives selling into fleets 3-100 trucks.

You will shape strategy, coach experienced AEs, and ensure the team achieves ambitious revenue targets in a segment with longer cycles and higher deal value. You will collaborate with Sales, Marketing, Product, Customer Success, and Finance to optimize processes and pricing for enterprise deals, while mentoring the team toward higher performance and