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Highway is the fastest-growing freight tech provider in North America, serving major freight brokers by solving carrier identity verification, fraud prevention, and supply chain transparency. The company is hiring a Sales Director to lead the Load Compliance business unit's day-to-day sales execution and team performance.
In this role, you will manage a team of Account Executives and drive consistent sales execution across pipeline creation, forecasting, coaching, and overall team performance. You'll report to the VP, Growth & Enablement and partner closely on implementing commercial priorities, reinforcing Highway's sales process, and ensuring the organization operates with discipline, accountability, and urgency.
Key responsibilities include:
- Team Management & Coaching: Manage daily performance of Load Compliance Account Executives through regular one-on-ones, coaching sessions, and performance reviews. Coach sellers through active opportunities, deal strategy, qualification, negotiation, and closing. Identify development opportunities and drive continuous improvement.
- Pipeline Management & Forecasting: Maintain a healthy pipeline through weekly inspections and forecast reviews. Challenge opportunity quality, stage progression, and close-date accuracy. Identify deal risk early and escalate opportunities requiring additional leadership support. Improve forecast accuracy and sales predictability.
- Sales Execution & Operating Discipline: Reinforce Highway's established sales process and operating standards. Hold the team accountable for CRM hygiene, opportunity quality, and required fields. Identify execution gaps and provide coaching. Surface process improvement opportunities through regular business inspection.
- Cross-Functional Partnership: Work with VP, Growth & Enablement on sales priorities and strategic programs. Collaborate with Marketing on lead quality and campaign execution. Partner with Revenue Operations on reporting and analytics. Provide structured feedback to Product and Customer Experience teams.
This is a strong fit for a frontline sales leader who enjoys coaching, inspecting the business, and building high-performing teams in a fast-moving commercial environment.
Qualifications:
- Bachelor's degree in Business Administration, Economics, Finance, or related field (required)
- 3+ years of experience managing B2B SaaS or technology sales teams (required)
- Proven track record of delivering revenue through a high-performing sales team (required)
- Experience managing both Account Executives and Business Development Representatives (required)
- Strong pipeline management and forecasting experience (required)
- Demonstrated ability to coach sellers through complex opportunities (required)
- Experience working with Salesforce, Gong, and modern sales technologies (required)
- Excellent communication, coaching, and leadership skills (required)
- High ownership, sound judgment, and ability to thrive in fast-paced environments (required)
Preferred Qualifications:
- Logistics, transportation, or supply chain technology experience
- Experience selling multi-product SaaS or platform solutions
- Experience in high-growth organizations
- Experience managing both inbound and outbound new business motions
- Experience working with enterprise and strategic accounts
