Head of Sales, Brokerage

Responsibilities

In the First 90 Days — Sell

• Take over active prospecting immediately and carry a personal quota from day one.
• Identify the most winnable customer segments and develop a target account list.
• Build relationships through outbound — cold calls, warm introductions, in-person visits where it matters.
• Close new accounts across any mode: TL, LTL, drayage, intermodal.
• Work closely with operations to ensure early wins are serviced well and retained.

Ongoing — Build

• Develop the sales playbook: ideal customer profile, outreach approach, pitch, objection handling, and close process.
• Define what ‘good’ looks like for a salesperson: activity metrics, pipeline standards, conversion benchmarks.
• Identify where current sales efforts are breaking down and fix them.
• Collaborate with account management to ensure clean handoffs and retention.

As We Scale — Coach & Hire

• Recruit and hire additional salespeople once the playbook is proven.
• Coach and develop the sales team — ride-alongs, deal reviews, pipeline coaching.
• Set team quotas and hold people accountable.
• Report on pipeline, forecast, and performance to leadership.
• Maintain a personal quota indefinitely (player-coach role).

Requirements

• Built a book of business from cold or near-cold outreach (not inherited accounts or inbound leads at large brokers).
• Comfortable with outbound selling: cold calls, in-person visits, building relationships over time.
• Closed freight accounts based on service, reliability, and relationships (not brand recognition).
• Sold freight brokerage services with understanding of modes (TL, LTL, drayage, intermodal), lanes, carrier relationships, and shipper needs.
• Can speak credibly to transportation managers or VPs of logistics about brokerage operations and margins.
• 3–5 years of freight brokerage sales experience, ideally at a smaller or mid-size shop.
• Managed salespeople before or clearly ready to; able to articulate development approach.
• Systems thinker who wants to build repeatable processes.
• Comfortable with ambiguity, thrives in scrappy environments with ownership and impact.
• Self-managed, proactive, and motivated by performance-based compensation.

Compensation

• Base Salary: $90,000+ depending on experience.
• Variable: Commission on gross margin from personally brought-in accounts (target variable equals base at quota).
• OTE: $180,000+ at quota (uncapped above that).
• 50/50 base and variable split.
• Income stream continues from retained accounts.