# Head of Sales, Brokerage

**Company:** [Cloudtrucks](https://hotfix.jobs/companies/cloudtrucks)
**Location:** Remote
**Role:** Sales Engineering
**Salary:** $90k – $180k/yr
**Experience:** 5+ years
**Skills:** Freight Brokerage Sales, Outbound Prospecting, Cold Calling, Relationship Building, Tl Sales, Ltl Sales, Drayage Sales, Intermodal Sales, Sales Playbook Development, Sales Coaching, Pipeline Management, Gross Margin Selling
**Posted:** 2026-07-22

> Player-coach Head of Sales responsible for building a repeatable outbound freight brokerage sales motion from scratch while carrying a personal quota. Requires 3-5+ years freight brokerage sales experience closing business through relationships and hustle (not brand), plus ability to develop playbooks, hire, and coach a team.

## Job Description

## 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.

## Similar jobs

- [Director, Enterprise Sales](https://hotfix.jobs/jobs/d63e629e-bf84-4813-a4b1-281a4b9a474f) - Datadog - Remote - $150k – $200k/yr
- [Director, Enterprise Sales Engineering - US](https://hotfix.jobs/jobs/04e491a3-af1d-482c-9c2e-9880042617a3) - Datadog - Illinois - $180k – $240k/yr
- [Director of Solutions Engineering - EMEA Enterprise](https://hotfix.jobs/jobs/5a2fd0e4-946e-483b-8bfc-2bac2b163f51) - Decagon - London, United Kingdom - £200k – £250k/yr
- [Director of Solutions Engineering - EMEA Strat](https://hotfix.jobs/jobs/7b3c6a30-d424-466d-bdeb-5a7e40c59525) - Decagon - London, United Kingdom - £200k – £250k/yr
- [Director, Field Engineering](https://hotfix.jobs/jobs/b8020e87-667a-4a1c-8028-7886b563496c) - Databricks - Toronto, Canada - CA$221k – CA$304k/yr

**Apply:** https://hotfix.jobs/jobs/a29474ca-559e-41b7-9d39-58a2ef421a64
**Canonical:** https://hotfix.jobs/jobs/a29474ca-559e-41b7-9d39-58a2ef421a64