Director of Sales

Hirewell; Illinois; Hybrid; USD 120,000 - 140,000; Full time

Benefits offered by this job

Medical, dental, and vision insurance

401(k) with company match

Flexible Spending Account (FSA)

Life and AD&D insurance

Long-term disability

Job summary

Hirewell is seeking a Director of Sales in Oakbrook Terrace, Illinois, to drive new logo acquisition in the time-sensitive transportation sector. This is a hunter role with no direct reports, focused on building a high-impact sales pipeline and expanding national coverage.

The successful candidate will own full sales cycles, travel locally and nationally, and collaborate with Pricing, Operations, and Executive Leadership to secure and grow strategic accounts while meeting aggressive revenue

Qualifications

• 10+ years of direct selling experience in domestic air freight or closely aligned niche.
• Proven track record of new logo wins and quota attainment.
• Deep understanding of multimodal transportation and time-critical service requirements.
• Strong negotiation skills and ability to close complex deals with midmarket and enterprise customers.

Responsibilities

• New Logo Acquisition: Aggressively pursue and close new business opportunities within a specialized logistics niche.
• Prospecting and Pipeline Generation: Build and maintain a robust pipeline through targeted outreach and industry networking.
• Customer Engagement: Conduct regular customer visits locally and nationally to advance deals and uncover expansion opportunities.
• Deal Execution: Lead the full sales cycle from initial outreach to contract signature with disciplined qualification.
• Account Expansion: Grow wallet share within new accounts by identifying additional lanes, modes, and service opportunities.
• Competitive Positioning: Articulate value proposition against competitors in time-critical transportation environments.
• Internal Coordination: Work with Pricing, Operations, and Executive Leadership for seamless onboarding and strong customer experience.

Skills

Direct selling

New logo acquisition

Negotiation

Relationship building

Presentation skills

Travel willingness

Job description

Director of Sales

Oakbrook Terrace, Illinois

Direct Hire

Salary Range : $120,000 - $140,000

Benefits : Medicaldentaland vision insurance; 401(k) with discretionary companymatch; Flexible Spending Account (FSA); Life and AD&D insurance; long-term disabilitycoverage,

Role Overview

The Director of Sales is a high impact hunter responsible for driving new logo acquisition and expanding the company’s footprint across targeted verticals. This role is built for a proven logistics salesperson who thrives on prospecting, winning, and growing accounts in a fast moving, timecritical transportation environment. This is an individual contributor role with no direct reports. Success is measured by personal sales production, not team management.

Key Responsibilities

• New Logo Acquisition: Aggressively pursue and close new business
• opportunities within aspecialized logistics niche.
• Prospecting andPipeline Generation: Build and maintain a robust pipeline through targeted outreach, industry networking, and strategic territory development.
• Customer Engagement: Conduct regular customer visits locally and nationally to advance deals, strengthen relationships, and uncover expansion opportunities.
• Deal Execution: Lead the full sales cycle from initial outreach to contract signature, ensuring disciplined qualification and strong close rates.
• Account Expansion: Grow wallet share within newly acquired accounts by identifying additional lanes, modes, and service opportunities.
• Competitive Positioning: Articulate the company’s value proposition clearly and persuasively against competitors in timecritical transportation.
• Internal Coordination: Work with Pricing, Operations, and Executive Leadership to ensure seamless onboarding and strong customer experience.

Performance Expectations

• Annual New Revenue Target: Produce $2M in new revenue annually.
• Pipeline Coverage: Maintain an active pipeline of 15-20 opportunities at all times, representing $5M in potential revenue.
• New Account Growth: Close 15+ new accounts per year.

Required Qualifications

• 10+ years of direct selling experience in domestic air freight, specialized ground services (white glove, box truck, sprinter vans, etc.) or a closely aligned niche.
• Proven track record of newlogo wins, aggressive prospecting, and consistent quota attainment.
• Deep understanding of multimodal transportation and timecritical service requirements.
• Strong negotiation skills and the ability to close complex deals with midmarket and enterprise customers.
• Ability to work primarily inoffice at Oak Brook Terrace, with flexibility.
• Willingness to travel for customer meetings (local + national), though travel is not excessive.
• Excellent communication, presentation, and relationshipbuilding skills.

Preferred Qualifications

• Existing customer relationships and the ability to bring business (not required).
• No active nonsolicit or restrictive covenant limiting customer engagement.
• Experience selling in highservice, timecritical transportation environments.
• Strong industry network and established reputation

Success Profile

The ideal candidate is a relentless hunter: competitive, resourceful, and highly skilled at opening doors and closing deals. They excel in fastpaced environments, know how to navigate complex logistics challenges, and consistently deliver new revenue. They bring urgency, discipline, and a strong commercial presence to every customer interaction.