Director of Sales

Monson Group; Chicago (IL); On-site; USD 120,000 - 180,000; Full time

Job summary

Monson Group is seeking a Director of Sales in Chicago to lead the sales organization and drive growth in transportation and logistics. You will own revenue, build a scalable sales process, and develop a high-performing team, collaborating with Operations and Carrier Sales to ensure exceptional execution from sale to service.

The role requires hands-on leadership, a track record of acquiring new business, expanding existing accounts, and coaching sales professionals in a fast-paced,

Qualifications

• 5+ years of sales experience in transportation, logistics, freight brokerage, 3PL, or a related industry
• Proven track record of generating new business and growing revenue
• Previous sales leadership or management experience
• Strong understanding of freight brokerage and transportation
• Demonstrated ability to build, coach, and manage a sales team
• Strong business development and prospecting skills
• Excellent communication, negotiation, and relationship-building abilities
• Competitive, driven, and results-oriented
• Strong leadership and decision-making skills
• Comfortable operating in a fast-paced, entrepreneurial environment
• Strong organizational and analytical skills
• Willingness to take ownership and be accountable for results

Responsibilities

• Lead the overall performance and direction of the sales organization
• Develop and execute a strategy for sustainable revenue and gross profit growth
• Establish individual and team sales goals, KPIs, activity standards, and performance expectations
• Build a consistent and scalable sales process
• Manage pipeline, conversion rates, revenue, gross profit, customer acquisition, and retention
• Identify new markets, industries, customers, and growth opportunities
• Stay current on transportation market conditions, pricing, capacity, and industry trends
• Hire, onboard, train, coach, and develop sales professionals
• Build and retain a high-performing sales team
• Create a culture of accountability, urgency, teamwork, and performance
• Conduct regular performance reviews and provide ongoing coaching
• Identify and develop future sales leaders
• Address performance issues quickly and appropriately
• Determine when additional sales resources are needed and participate in recruiting efforts
• Hold the team accountable for established goals and objectives
• Personally participate in major customer opportunities and strategic sales initiatives
• Develop relationships with key decision-makers
• Generate new business through prospecting, networking, referrals, and industry relationships
• Lead customer presentations, negotiations, and major account opportunities
• Develop strategies to grow existing accounts
• Identify opportunities to diversify the customer base and revenue mix
• Partner with Operations to ensure sales commitments can be executed successfully
• Work closely with Carrier Sales on capacity and competitive pricing
• Maintain strong communication between Sales, Operations, and executive leadership
• Help build processes that create a seamless customer experience
• Provide market intelligence and customer feedback to leadership

Skills

5+ years sales experience in transport

Proven new business growth

Sales leadership/management

Freight brokerage knowledge

Build/coach/manage sales team

Business development/prospecting

Excellent communication/negotiation

Results-driven

Leadership/decision-making

Fast-paced entrepreneurial mindset

Strong organizational/analytical

Own accountability for results

Job description

Director of Sales

Location: Chicago - Downtown
Industry: Transportation & Logistics
Position Type: Full-Time, On-site

The Opportunity

Our client is a growing transportation and logistics company looking for an experienced Director of Sales to lead its sales organization and help drive the next stage of growth.

This is a high-impact leadership role with significant ownership and visibility. The Director of Sales will be responsible for sales performance, new business development, team leadership, and building a scalable sales organization.

This is not a position for someone who simply wants to manage from the sidelines. The right person will be a hands-on sales leader who can develop people, create accountability, win business, and help shape the company's overall sales strategy.

Position Overview

The Director of Sales will be responsible for driving revenue and gross profit growth through new customer acquisition, expansion of existing accounts, and development of the sales team.

This individual will work closely with executive leadership, Operations, and Carrier Sales to ensure customer expectations align with operational capabilities and that the organization delivers a strong customer experience from initial sale through ongoing execution.

Key Responsibilities

Sales Leadership & Strategy

• Lead the overall performance and direction of the sales organization


• Develop and execute a strategy for sustainable revenue and gross profit growth


• Establish individual and team sales goals, KPIs, activity standards, and performance expectations


• Build a consistent and scalable sales process


• Manage pipeline, conversion rates, revenue, gross profit, customer acquisition, and retention


• Identify new markets, industries, customers, and growth opportunities


• Stay current on transportation market conditions, pricing, capacity, and industry trends

Team Leadership & Development

• Hire, onboard, train, coach, and develop sales professionals


• Build and retain a high-performing sales team


• Create a culture of accountability, urgency, teamwork, and performance


• Conduct regular performance reviews and provide ongoing coaching


• Identify and develop future sales leaders


• Address performance issues quickly and appropriately


• Determine when additional sales resources are needed and participate in recruiting efforts


• Hold the team accountable for established goals and objectives

Business Development

• Personally participate in major customer opportunities and strategic sales initiatives


• Develop relationships with key decision-makers


• Generate new business through prospecting, networking, referrals, and industry relationships


• Lead customer presentations, negotiations, and major account opportunities


• Develop strategies to grow existing accounts


• Identify opportunities to diversify the customer base and revenue mix

Cross-Functional Leadership

• Partner with Operations to ensure sales commitments can be executed successfully


• Work closely with Carrier Sales on capacity and competitive pricing


• Maintain strong communication between Sales, Operations, and executive leadership


• Help build processes that create a seamless customer experience


• Provide market intelligence and customer feedback to leadership

Qualifications

• 5+ years of sales experience in transportation, logistics, freight brokerage, 3PL, or a related industry


• Proven track record of generating new business and growing revenue


• Previous sales leadership or management experience


• Strong understanding of freight brokerage and transportation


• Demonstrated ability to build, coach, and manage a sales team


• Strong business development and prospecting skills


• Excellent communication, negotiation, and relationship-building abilities


• Competitive, driven, and results-oriented


• Strong leadership and decision-making skills


• Comfortable operating in a fast-paced, entrepreneurial environment


• Strong organizational and analytical skills


• Willingness to take ownership and be accountable for results

What Success Looks Like

Success in this role will be measured by the ability to:

• Grow revenue and gross profit


• Win new customers


• Expand existing accounts


• Build and retain a high-performing sales team


• Develop future sales leaders


• Create accountability and consistency within the sales organization


• Build a scalable and repeatable sales process


• Strengthen the company's competitive position in the transportation market

Why This Opportunity

This company is at an important stage of growth and is investing in its people, technology, systems, and processes.

The Director of Sales will have the opportunity to help shape the sales organization rather than simply inherit an established structure. This person will have meaningful input into hiring, sales strategy, team development, and how the company approaches growth.

It's a strong opportunity for a hands-on sales leader who wants ownership, accountability, and the ability to make a measurable impact on the business.