Senior Director of Field Sales

COMPANY OVERVIEW

CrossCountry Freight Solutions (CCFS) is an exceptional company with a mission to achieve universal prosperity with our Customers, Company, Team Members, & Communities. We use the latest technology to provide quality service and on-time delivery to our customers. CCFS provides direct service throughout the Western and Central United States. We look forward to having you Hitch on and Prosper with us!

JOB TITLE

Senior Director of Field Sales

DEPARTMENT

Business Development

JOB STATUS

Exempt

COMPENSATION

$140,000 - $150,000 + Incentive (based on experience and skills)

LOCATION

Dallas, TX

REPORTS TO

VP of Business Development

DIRECT REPORTS

Yes

JOB SUMMARY

CrossCountry Freight Solutions is looking for a data-driven, coaching-focused sales leader who thrives on developing people, driving accountability, and aligning a distributed team to a unified strategy. In this position, you will lead a high-performing Field Sales organization of 20–30 representatives responsible for $75–100M+ in annual revenue across multiple territories. Oversee three Regional Sales Managers with planned expansion as the organization grows, and directly manage 4–8 representatives in strategic territories. Your primary mission: Ensure each individual on the team performs at their highest possible level—hitting revenue targets, following sales processes, developing their skills, and retaining customers at 99%+ rates. This is 90% a management role focused on coaching, accountability, performance management, and team development. You will execute sales strategy set by the VP of Sales, driving consistent execution across all territories while developing your Regional Managers and building a promotion pipeline from Outside Sales → Senior Outside Sales.

ESSENTIAL JOB DUTIES

Team Performance Management (60%)

• Drive individual rep performance across all metrics: revenue achievement, pipeline health, CRM compliance, customer retention
• Conduct weekly one-on-one meetings with Regional Sales Managers and direct report reps
• Review data and metrics to identify performance gaps and coaching opportunities
• Develop and execute performance improvement plans for underperforming reps
• Hold team and individuals accountable to sales process, CRM discipline, and company standards
• Conduct field ride-alongs for special situations (struggling reps, new markets, development opportunities)
• Make tough personnel decisions: recommend terminations, PIPs, demotions to VP of Sales
• Celebrate wins and recognize top performers to drive engagement and retention

Regional Sales Manager Development (20%)

• Coach and develop Regional Sales Managers on leadership, coaching, and accountability
• Ensure Regional Managers are executing company strategy and processes consistently
• Review Regional Manager performance on team metrics, hiring, and people development
• Align Regional Managers on territory design, quota setting, and resource allocation in collaboration with VP of Sales
• Address Regional Manager performance gaps through coaching, PIPs, or role changes as needed
• Develop succession pipeline for Regional Manager roles

Hiring & Team Building (10%)

• Final approval on all hires made by Regional Managers (ensure hiring standards are met)
• Directly hire 3-4 sales reps for strategic territories not covered by Regional Managers
• Fill open positions quickly with high-quality candidates
• Partner with recruiting and HR to build talent pipeline
• Ensure consistent use of hiring profiles, PI assessments, internal resources, and structured interview processes
• Drive retention of top performers through engagement, development, and career pathing, making promotion recommendations when possible

Strategy Execution & Cross-Functional Leadership (10%)

• Execute sales strategy, processes, and systems defined by VP of Sales
• Collaborate with VP on territory design and quota setting
• Influence (but not own) compensation plan design through feedback to VP
• Work cross-functionally with Operations, Pricing, Customer Service, and Finance as needed
• Influence Sales Operations on CRM administration, reporting, and analytics needs
• Represent Outside Sales leadership in company strategic discussions
• Forecast revenue and provide business updates to VP and executive team

MINIMUM REQUIREMENTS

• Minimum: 5+ years sales leadership experience, including 2+ years managing managers (not just individual contributors)
• Experience managing field sales teams of 15+ representatives
• Proven track record improving underperformer performance or making tough personnel decisions
• Experience with structured sales processes, CRM systems, and data-driven management
• Demonstrated success hiring, developing, and retaining sales talent
• Data-driven leadership: Comfortable with metrics, dashboards, analytics, CRM reporting
• Coaching ability: Can develop people through one-on-ones, feedback, and skill-building
• Accountability: Willing to have tough conversations and make difficult personnel decisions
• Influence without authority: Can align Regional Managers who have significant autonomy
• Hiring judgment: Makes good talent decisions and doesn't settle for wrong fits
• Freight Technology proficiency: CRM systems, Shipper Platforms (MyCarrier, Kuebix, FreightView), Microsoft Office Products (Teams, Excel), data/reporting tools (PowerBi)
• Executive presence: Can represent sales leadership in company strategic discussions and presentations

BENEFITS

• Medical, Vision, Dental, Supplemental, and Life Insurances available.
• Paid time off, paid holidays, paid community volunteer time
• 401k retirement plan

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