Freight Sales Leader — Build & Scale (Remote)

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

Job summary

CloudTrucks is seeking a Head of Sales, Brokerage to design and execute a new sales motion across TL, LTL, drayage, and intermodal. This player-coach role starts with a personal quota and evolves into building the playbook, metrics, and team as we scale.

You will prospect, close new accounts, and collaborate with operations to service and retain early wins. Remote in the US; you’ll own the territory and report to leadership.

Qualifications

• Built a book of business from cold or near-cold outreach, not from inbound leads.
• Sold freight brokerage services across TL, LTL, drayage, and intermodal.
• 3–5 years of freight brokerage sales experience, preferably in smaller shops.

Responsibilities

• Take over active prospecting immediately with a personal quota.
• Identify winnable customer segments and develop a target account list.
• Build relationships through outbound calls, warm introductions, or in-person visits.
• Close new accounts across TL, LTL, drayage, and intermodal.
• Collaborate with operations to service and retain early wins.
• Develop the sales playbook including ICP, outreach, pitch, and close process.
• Define success metrics, pipeline standards, and conversion benchmarks.
• Coach and hire additional salespeople and build a scalable team.

Skills

Cold Calling

Relationship Building

Sales Leadership

Hunter Mentality

Job description

CloudTrucks is seeking a Head of Sales, Brokerage to design and execute a new sales motion across TL, LTL, drayage, and intermodal. This player-coach role starts with a personal quota and evolves into building the playbook, metrics, and team as we scale.

You will prospect, close new accounts, and collaborate with operations to service and retain early wins. Remote in the US; you’ll own the territory and report to leadership.