Freight Sales Leader: Build & Scale Remote Playbook

CloudTrucks; San Francisco (CA); On-site; USD 81,000 - 99,000; Full time

Benefits offered by this job

Remote work

Job summary

CloudTrucks is seeking a Head of Sales, Brokerage to design and scale a repeatable sales motion across freight modes. You will sell, build the system, and eventually lead the team, while maintaining a personal quota from day one.

This hunter role emphasizes relationship-building, outbound prospecting, and coaching. Remote with flexibility to manage territory, you will report to leadership and shape the sales org as it grows.

Qualifications

• 3–5 years freight brokerage sales experience, ideally in smaller or mid-size shops.
• Proven ability to build relationships and close business on service and hustle.
• Experience selling across TL, LTL, drayage, and intermodal.

Responsibilities

• In the first 90 days, carry a personal quota and prospect aggressively.
• Identify target segments and build a credible target account list.
• Outreach via calls, warm intros, and in-person visits where relevant.
• Close new accounts across all supported modes and ensure early wins are serviced.
• Develop the sales playbook, including ICP, outreach, pitch, and close process.
• Define success metrics for activity, pipeline, and conversion.
• Recruit, coach, and hire additional salespeople as the playbook proves.
• Set quotas, supervise performance, and report progress to leadership.
• Maintain personal quota as the team scales and lead by example.
• Operate in a smaller, flexible org with ownership and impact.

Skills

Cold outreach

Account prospecting

Freight brokerage sales

Closing deals

Building sales playbooks

Coaching & hiring

Quota ownership

Job description

CloudTrucks is seeking a Head of Sales, Brokerage to design and scale a repeatable sales motion across freight modes. You will sell, build the system, and eventually lead the team, while maintaining a personal quota from day one.

This hunter role emphasizes relationship-building, outbound prospecting, and coaching. Remote with flexibility to manage territory, you will report to leadership and shape the sales org as it grows.