Demo

Business Development Sales Representative

Headwall Logistics LLC
Chicago, IL Full Time
POSTED ON 11/23/2025
AVAILABLE BEFORE 5/18/2026

Job description - This is an in-office role in Denver, CO


ABOUT US

Founded by brothers Dave and Steve Peek, this high energy company provides businesses the tools and resources they need to complete their shipping needs. Headwall isn't just a name; it embodies our entire approach. The headwall of a mountain is the steepest cliff and often the most difficult to ascend. Our clients come to us time and time again because we never shy away from the ascent, regardless of the pitch.

Delivering for our clients is made possible by our team's commitment to Headwall's core values, practiced daily as we act as strategic partners for our clients:


  • Solutions. Solutions. Solutions: We are solvers. We are fixers. We are outcome oriented.
  • Integrity: We say what we mean and do what we say. That simple.
  • Details Are Everything: We live in the details so our clients can focus on the results.
  • Family Mentality: Whether a client, carrier, or employee, we look out for our people.


ROLE – Business Development Sales Representative

This is an in-office role in Denver, CO (remote work is not available) – minutes from downtown, 1 mile from Sloan’s Lake, and conveniently located in the heart of the Highlands.


Headwall Sales offers a unique and fun sales environment fueled by the nonstop pace of the transportation industry. We provide solutions across multiple modes; including flatbed, dry van, hot shot, and specialized freight projects. Our team thrives in a fast-paced atmosphere where competition and camaraderie go hand in hand.


Headwall Sales offers many incentives like team outings, happy hours, and personalized coaching. We take pride in all aspects of the company being accessible and investing in our employee's success and development. Employee engagement is at the heart of the organization and incredibly important to us.


You Will:

  • Training & Development: Complete Headwall training that preps you for your new team – one on one coaching throughout your career to development new and fresh sales strategies
  • Prospecting & Business Development: Call customers daily to generate new business, develop deep relationships, and grow your book of business
  • Account Management: Outbound calling, quoting freight, coordinating with operations, updating CRM and building relationships with clients
  • Internal Collaboration: Cross functionally with operations to ensure delivery of Headwall’s tracking and customer service standards
  • Become an expert in overcoming objections to business owners over the phone
  • Collaborate with leadership and other team members to continue to master your sales pitch


Career Growth– What to Expect:

  • Experience personalized one-on-one coaching to become a sales expert
  • Opportunity to manage account teams through book of business
  • Leadership that is invested in your success and development
  • Additional leadership training offered throughout time of employment
  • Direct contact, coaching, and mentoring from the founders of the company


What we are looking for:

  • Bachelor’s degree in Business preferred
  • 1-3 years of Experience and/or intense interest in sales, pipeline management, and negotiations
  • You're not afraid to fail and you can recover quickly from difficult objections - rejection doesn’t get to you
  • Ability to think on your feet and pivot quickly when selling to businesses over the phone
  • You’re an excellent listener and you can communicate clearly & concisely both verbally and in written forms
  • Strong ability to adapt and possess a coachable mindset - you'll receive frequent coaching
  • Openness to growth and desire for leadership opportunities a plus
  • Desire to work hard and exceed goals- you’re not satisfied unless you’re the best


Benefits & Compensation:

  • Base salary and uncapped commission – expected first year earnings of 72k to 90k
  • Ongoing bonus opportunities and incentives
  • Team outings, events, and a supportive, high-energy environment
  • Employer paid medical coverage
  • 401(k) with company matching


Headwall Logistics LLC provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.

This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation and training.


Salary : $72,000 - $90,000

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