The Role
Leads recruiting and engagement across multiple markets for independent contractor drivers. Responsibilities include coaching a recruiting team, setting sourcing priorities, improving activation and retention, analyzing turnover, managing orientations, resolving driver issues, overseeing recruiting and contractor platforms, coordinating vendors, auditing market practices, and delivering performance reporting. The role requires regular travel, frontline recruiting support, and cross-functional partnership with Operations.
Summary Generated by Built In
Recruiting & Engagement Supervisor
Location: On Site
Compensation: $65,000–$70,000 annually + up to $4,000 annual bonus, paid quarterly
Direct Reports: 3
Travel: Regular travel to company markets
We Find A Way.
At Crossroads Courier, every delivery matters.
From life-saving medical shipments to critical business deliveries, our team helps customers solve urgent logistics challenges every day.
We are seeking a Recruiting & Engagement Supervisor to lead the team responsible for attracting, activating, engaging, and retaining independent contractor drivers across our growing multi-market footprint. This working-supervisor role travels regularly to our markets, including Phoenix, Las Vegas, Tucson, Kansas City, and new markets added as the business grows.
This is not a behind-the-desk leadership role. You’ll coach and develop the team, set market recruiting priorities, step into frontline work when needed, and use data and firsthand experience to continuously improve recruiting, activation, and driver retention.
What You’ll Do
- Lead, coach, and develop the Recruiting & Engagement team across multiple markets.
- Set market priorities and sourcing strategies based on validated driver demand.
- Set clear expectations and hold the team accountable for show rate, activation, engagement, early loss, and 90-day driver retention.
- Analyze driver turnover and partner with Operations to identify root causes and execute targeted action plans.
- Serve as project manager for driver sourcing tied to new customer onboarding, including developing the sourcing strategy, distributing work across the team, monitoring results, and executing additional sourcing levers as needed.
- Develop and maintain a department best-practices toolbox, including vehicle requirements, sourcing strategies, and market-specific recruiting practices.
- Operate with curiosity by experiencing the process from the driver’s perspective, including finding our ads, going through the application process, and identifying opportunities to reduce friction and improve the overall driver experience.
- Continuously identify and implement opportunities to improve the driver experience, reduce preventable early loss, and strengthen 90-day driver retention.
- Improve conversion throughout the driver journey, from initial interest and application through orientation and first delivery.
- Step in to support frontline driver recruiting, screening, orientation, activation, engagement, and advanced driver orientation when additional capacity or urgency requires it.
- Own the content and administration of new and advanced driver orientation curriculum and coordinate client route orientations with Operations.
- Travel to divisions to audit recruiting and engagement practices, evaluate the driver experience, and provide feedback to the team.
- Own driver issue resolution, including settlement escalations, platform access, support coordination, and workflow governance.
- Oversee vendors and platforms supporting independent contractor sourcing, settlements, communication, and orientation, including Indeed, Open Force, CXT, Zello, and Zoho Recruit.
- Provide leadership with scorecards, risks, trends, and data-driven recommendations for improving performance.
What We’re Looking For
- 5+ years of relevant recruiting, staffing, workforce operations, orientation, or contractor-relations experience.
- 2+ years leading people, programs, or multi-market recruiting work.
- Demonstrated ability to improve recruiting, activation, quality, or retention outcomes.
- Strong coaching, facilitation, communication, and cross-functional partnership skills.
- Ability and willingness to travel regularly and step into frontline work when needed.
Preferred Experience
- Independent contractor, transportation, logistics, staffing, or field-workforce experience.
- OpenForce or comparable contractor settlement platform experience.
- Indeed, Zoho Recruit/CRM, CXT, Zello, screening, survey, or dashboard experience.
- Curriculum development, training, vendor management, or process-governance experience.
How Success Will Be Measured
- Stronger 90-day driver retention and reduced preventable early turnover.
- Consistent show rates and activation conversion across markets.
- Validated market needs filled with qualified, active drivers.
- Consistent team performance, accountability, and orientation quality.
- Accurate reporting, reliable contractor processes, and timely identification of workforce risks.
Why Crossroads Courier?
- Lead a function that has a direct impact on our ability to serve customers.
- Build and develop a growing team while still staying close to the work.
- Shape how we recruit, activate, engage, and retain drivers as we enter new markets and win new business.
- Solve real workforce challenges with the freedom to improve processes and build better ways of working.
- Gain visibility and partnership across Operations and company leadership.
If you are a hands-on talent or workforce leader who enjoys developing people, solving operational problems, improving systems, and driving measurable results, we would love to hear from you.
Crossroads Courier is committed to providing equal employment opportunities to all employees and applicants for employment. Employment decisions are based on business needs, job requirements, and individual qualifications, without regard to race, color, religion, sex (including pregnancy, sexual orientation, and gender identity), national origin, age, disability, genetic information, veteran status, or any other characteristic protected by applicable federal, state, or local law.
Skills Required
- 5+ years of relevant recruiting, staffing, workforce operations, orientation, or contractor-relations experience
- 2+ years leading people, programs, or multi-market recruiting work
- Demonstrated ability to improve recruiting, activation, quality, or retention outcomes
- Strong coaching, facilitation, communication, and cross-functional partnership skills
- Ability and willingness to travel regularly and perform frontline work when needed
- Independent contractor, transportation, logistics, staffing, or field-workforce experience
- OpenForce or comparable contractor settlement platform experience
- Indeed, Zoho Recruit or CRM, CXT, Zello, screening, survey, or dashboard experience
- Curriculum development, training, vendor management, or process-governance experience
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The Company
What We Do
Crossroads Courier is a privately held corporation, headquartered in St. Louis, Missouri, that provides a wide spectrum of time-critical, local and nationwide, courier and delivery services. From Warehousing and Logistics to scheduled or next-day deliveries, Crossroads Courier can handle all of your courier needs. The company is a customer-service driven organization that focuses on quality service for its clients and provides a positive workplace for its employees. Local Courier services throughout St. Louis, Kansas City, Phoenix and Las Vegas metro areas include: • On-demand Messenger Service • Rush Deliveries • Scheduled Courier Service • Next Day Distribution • Dedicated Route Service • Fleet Replacement Service • Line Haul Service • Critical Parts Storage
