Senior Sales Executive

Start Date: ASAP

Location: 444 N Wells St, Suite 202, Chicago, IL 60654

Type: Full-time, in-office

Reports To: Founder and CEO

Compensation: Market-competitive base salary plus uncapped 30% commission split. Equity in the company available to top producers based on performance, after 6 months of employment.

The Opportunity

Red Wolf Logistics is hiring a Senior Sales Executive to join the founding team. This is a hunting role for a proven cradle-to-grave broker who closes meaningful business fast, builds a book that compounds, and refuses to lose.

If you are tired of earning less commission % than you deserve, lacking the best tools, and having a ceiling on your earnings, this should be your next move.

Who We Are

Red Wolf Logistics is a US freight brokerage startup founded by operators who have scaled startups into billion-dollar businesses. Our service lines cover full truckload (dry van, reefer, flatbed), small truckload (sprinter vans, box trucks), partial truckload and LTL.

We chase Middle Market shippers ($50M to $750M) who move 50 to 500 loads per week. These are shippers who steadily feed us and value relationships, service, and communication more than price alone. We do not chase cheapest-quote wins the business shippers, and neither will you.

The WOLF Mentality

We are top-performing, highly driven individuals who possess grit, discipline, and a relentless, never-backing-down mentality to achieve our goals. Every person on this team operates with the WOLF mentality:

• Will. Underlying drive. Zero surrender.
• Ownership. Radical accountability. No excuses.
• Lock In. Disciplined focus on what matters.
• Ferocity. Relentless aggression toward obstacles and reaching our goals.

We all need someone to chase down. We want everyone else chasing us.

Grow or Die

Our strategy is simple: take every good load you can get and never give them back. Red Wolf operates on a grow-or-die principle. Speed to market and a relentless sense of urgency, every single day. Your book grows and skills sharpen month over month, or you are in the wrong seat. We hire, train, compensate, and promote to that standard. People who want to grow love this environment. People who want to coast or clock in and clock out do not last here.

Quality of customer and quality of loads beats quantity. Both matter. You will be measured on both.

Sell on Value, Not Price

Anyone can be the cheapest. We are not interested in that game and neither should you be. We win by:

• Understanding the shipper's business before we ever talk capacity
• Solving freight problems competitors will not touch
• Communicating proactively so the customer never has to chase us
• Delivering reliability that justifies a premium and earns repeat business

If your sales motion depends on undercutting the market, this is not the right role or company for you. If you know how to build trust with decision-makers and convert that trust into profitable, repeat freight, keep reading.

What You Will Do

• Hunt and close Middle Market shipper accounts ($50M to $750M) that fit our ICP and value service over rock-bottom price
• Own the full cradle-to-grave cycle: prospect, qualify, quote, win, onboard, operate, and grow each account
• Execute a streamlined sales process built on a modern CRM, ICP-aligned prospecting, direct contact data, and disciplined pipeline management
• Get in front of real decision-makers (VPs of Supply Chain, Transportation Managers, Logistics Directors) to identify prospective clients who transact on value and reliability
• Master pre-booking trucks and carrier utilization to protect margin and delight your customers
• Maintain a top-tier activity bar: calls, meetings, and pipeline coverage that match a producer who wins
• Meet prospects face-to-face
• Develop your own team of A-players once your volume justifies the expense of supporting your daily operations

Who You Are

• 5+ years in freight brokerage sales, cradle-to-grave, with a documented track record of quickly building a book from scratch and growing it
• You sell on value and have the wins to prove it. You can name customers who chose you over a cheaper competitor and tell us why
• You are fluent across modes: FTL (dry van, reefer, flatbed), partial, small truckload (sprinter, box truck), and LTL
• You can quote and win profitable freight, and protect margin without losing the relationship
• You operate with urgency. You return calls fast, follow up faster, and never let a deal sit because you got busy
• You want to be measured. You want a scoreboard. You want to win

What We Offer

• Compensation: Market-competitive base salary plus uncapped 30% commission
• Equity in the company. Top producers earn equity in Red Wolf based on performance. Sell at the level we expect, own a piece of what you build
• Wide-open market. No territory restrictions, no internal competition for accounts, minimal red tape
• Benefits: Health, dental, vision, 401(k), and 15 days PTO
• Founding team voice. You will shape how we sell, how we recruit, and how we operate

How to Apply

Email a short note and your track record to chris@redwolfgl.com. Tell us:

1. Your experience in cradle-to-grave freight brokerage sales
2. What makes you special, differentiating yourself from other candidates that apply. What modes and industries you will focus on and why
3. What your last twelve months of personal production looked like (revenue, margin, margin %, and customer count)

• Applications are reviewed daily. We move fast and so should you.