Director of Sales Fleet Services​/B2B​/Build & Scale

This is a rare opportunity to build and own an inside sales function from the ground up within a well-established, profitable B2B services organization serving commercial trucking fleets. Backed by significant growth capital and recently validated through a McKinsey-led review, the business is positioned for its next phase of scalable growth - and inside sales is a critical lever.

In this role, you will lead the design, execution, and scaling of an outbound inside sales organization focused on selling directly to trucking and fleet operators. You’ll take ownership of structure, tooling, KPIs, and team development - turning an underdeveloped function into a predictable, high-performing growth engine. This is a hands‑on leadership role where you’ll balance strategy with execution and work closely with senior leadership to define how inside sales operates moving forward.

• True build‑and‑scale leadership role - not inheriting a rigid playbook
• Ability to design the team your way (structure, segmentation, KPIs, tooling)
• Immediate team in place with clear runway to scale significantly
• High visibility and direct access to executive leadership and ownership
• Backed by a stable, profitable business with committed capital for growth
• Tangible, real‑world product serving essential commercial operations (not SaaS churn)
• Opportunity to leave a lasting mark on how the company sells going forward

• Base Salary: $150K+ (flexible for the right candidate)
• Bonus / OTE: ~20% bonus, uncapped
• Total On-Target Earnings: ~$180K+
• Benefits:
  Medical, Dental, Vision
• Retirement: 401(k) with company match
• Travel Expenses:
  Covered (limited travel; primarily office-based)
• Work Environment:
  In‑office role (Chicago/Schaumburg area) with potential flexibility over time

• Building structure where little exists today
• Leading a high-volume outbound sales environment with low initial hit rates
• Driving performance and accountability while scaling thoughtfully
• Creating momentum and early wins to unlock broader team growth

• 3+ years of inside sales / call center leadership experience
• Proven track record building, coaching, and scaling outbound sales teams
• Experience implementing dialers, Salesforce, and KPI-driven sales environments
• Comfortable owning both strategy and day-to-day execution
• Industry experience not required (business will teach the market)
• Education
• Bachelor’s degree preferred
• Not required for a strong, proven sales leader

This role requires resilience, discipline, and strong leadership instincts - but offers meaningful upside for someone who enjoys building from ambiguity.