Cradle to Grave Sales Manager

About RWB Trucking

RWB Trucking, LLC is a multi-office freight and logistics company built on “The RWB Way” — Relentless Service, Winning Culture, and Accountability. With offices spanning Woodridge, St. Charles, Tampa, River North, and beyond, RWB has grown into a trusted freight partner for shippers across the country. We're growing our sales leadership bench and looking for proven freight sales talent ready to take the next step into management

Our Culture & Values

At RWB, culture drives performance. Our team operates with a clear set of values that define how we work, serve, and grow together:

• Relentless Service – We go above and beyond to support our customers, carriers, and teammates.
• Winning Culture – We bring energy, urgency, and a competitive mindset to everything we do.
• Be Accountable – We take ownership of our work, our results, and our commitments.

• We believe success is built through execution, consistency, and doing the right thing — especially when it’s difficult.
• Why Join RWB Trucking?
• At RWB, we believe strong partnerships are built through trust, integrity, and consistent performance. We offer real opportunities for growth, advancement, and long-term career development within a fast-moving, performance-driven organization.
• If you are looking for a place where hard work is recognized, growth is earned, and performance matters, RWB Trucking is the place to build your future.

Equal Opportunity Employer

RWB Trucking is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or veteran status.

Requirements

• Proven success in full-cycle (“cradle to grave”) freight or 3PL sales — from prospecting through closing and account management.
• Experience operating at a senior account manager level or above, having grown and retained a meaningful book of business.
• A genuine interest in and readiness for a sales leadership/management role — you're ready to develop others, not just carry your own number.
• A track record of bringing on 20+ profitable new customer accounts over the course of your career.
• Experience mentoring, training, or coaching junior sales reps — whether formally or informally.
• Top-performer recognition (President's Club or equivalent) a plus.

Summary

RWB Trucking is hiring a Sales Manager to lead a team of New Account Executives (NAEs) through the full “cradle to grave” freight sales cycle — from prospecting and cold outreach through closing and onboarding new customers. This role is for an experienced freight sales professional who has already proven they can win business and is ready to build and coach a team that does the same.

Key Responsibilities

• Lead and coach a team of New Account Executives (NAEs) through the full freight sales cycle.
• Own the onboarding and ramp plan for new hires, with structured coaching — not just time on the calendar — to help new reps become productive faster.
• Set realistic quota and activity milestones for new reps based on where they are in their ramp, not an arbitrary calendar date.
• Run weekly 1-1s and call reviews coaching objection handling, call structure, and prospecting discipline.
• Partner with recruiting on hiring decisions for your team.
• Lead ongoing training sessions to keep your team's skills sharp.