Director, Strategic Sales

Description
We’re looking for a Strategic Sales Director who will drive profitable growth by building new customer relationships and selling brokerage and asset-based transportation solutions across the U.S.

This is a full-cycle sales role combining BDR-generated opportunities with independent business development. You’ll own opportunities from initial discovery through contract execution and successful customer launch, while building a strong individual pipeline and expanding customer relationships.

The ideal candidate understands transportation and logistics, is confident prospecting and negotiating, and knows how to turn customer needs into profitable, executable solutions while maintaining an accurate and actionable Salesforce pipeline.

Key Responsibilities
Sales Discovery & Qualification

Conduct discovery calls and meetings scheduled by BDRs and qualify opportunities based on freight profile, lanes, modes, volume, seasonality, service requirements, urgency, and revenue potential.
Identify customer pain points, decision-makers, purchasing processes, competitive alternatives, and implementation timelines.
Determine fit across brokerage, asset-based, and blended transportation solutions while establishing clear next steps and maintaining sales momentum.

Pipeline Generation

Build a self-generated pipeline through outbound calls, email, referrals, networking, account research, dormant-account outreach, and other prospecting activities.
Develop targeted account plans based on assigned industries, territories, freight modes, or customer segments.
Balance BDR-generated opportunities with independently sourced business and re-engage stalled, inactive, and previously lost opportunities.
Maintain sufficient pipeline coverage to support revenue and gross-profit targets.

Solution Development & Sales Execution

Develop and sell transportation solutions aligned with customer operational and commercial requirements, including truckload, LTL, expedited, dedicated, drayage, specialized transportation, and other brokerage or asset-based services.
Partner with pricing, operations, capacity, and carrier teams to develop competitive, operationally viable proposals.
Prepare and deliver presentations, proposals, pricing packages, and service recommendations.
Clearly communicate the capabilities and limitations of brokerage and asset-based solutions.
Negotiate rates, commercial terms, payment expectations, and service-level commitments while closing profitable business and protecting service quality.

Salesforce & Forecast Management

Maintain accurate account, contact, activity, and opportunity records, including customer requirements, risks, communications, next steps, values, close dates, probabilities, and loss reasons.
Advance opportunities through established sales stages based on verified customer actions and manage follow-up tasks to prevent stalled opportunities.
Provide reliable weekly, monthly, and quarterly forecasts while maintaining strong CRM data quality and avoiding duplicate, inflated, or unsupported opportunities.

Customer Onboarding & Account Growth

Coordinate contracts, credit approval, insurance requirements, system setup, pricing, and operational handoff.
Ensure operations receives clear documentation of customer requirements, lanes, rates, service commitments, communication expectations, and escalation procedures.
Remain engaged through initial shipments to support a successful launch and partner with operations and account management to address early service issues.
Identify opportunities to expand customers into additional lanes, locations, modes, or services while supporting retention and profitable account growth.

Cross-Functional Collaboration

Provide BDRs feedback on lead quality, targeting, messaging, and follow-up.
Partner with operations, pricing, capacity, carrier management, and account management to ensure solutions are executable, competitive, and profitable.
Communicate customer expectations clearly and promptly escalate service risks, capacity constraints, pricing changes, credit concerns, claims, and other potential barriers.
Performance Expectations

Success in this role may be measured by:

New revenue and gross profit generation
New customers acquired and activated
Gross margin or gross profit per shipment
Qualified pipeline value and coverage
Self-generated pipeline and revenue contribution
Sales-stage conversion rates
Qualified meetings, proposals, and closed opportunities
Sales-cycle length

Salesforce activity, accuracy, and data quality
Required Qualifications
5+ years of experience in transportation, logistics, freight brokerage, asset-based transportation, or B2B sales.
Demonstrated ability to prospect, qualify, manage a pipeline, negotiate, and close business.
Strong communication, presentation, relationship-building, organization, and follow-up skills.
Ability to understand transportation requirements and translate them into viable solutions.
Ability to collaborate effectively across BDR, pricing, operations, capacity, carrier management, and account-management teams.
Strong commercial judgment and understanding of the relationship between pricing, service, capacity, and profitability.

Preferred Qualifications
Knowledge of the U.S. freight and transportation market.
Experience selling to Enterprise-level shippers.
Experience selling both brokerage and asset-based services.
Familiarity with truckload, LTL, expedited, dedicated, drayage, or specialized transportation.
Established shipper or transportation decision-maker relationships.
Proven success achieving revenue, gross-profit, and new-business targets.
Experience using Salesforce or a comparable CRM.

Role Ownership

The Strategic Sales Director owns each sales opportunity from discovery through signed agreement and successful operational launch. Day-to-day shipment execution generally remains with operations or account management, allowing the Strategic Sales Director to stay focused on prospecting, closing new business, and expanding customer relationships.