Recruiting & Engagement Supervisor

Crossroads Courier•Saint Louis, MO

1d•Onsite

About The Position

Crossroads Courier is seeking a hands-on Recruiting & Engagement Supervisor to lead the team responsible for attracting, activating, engaging, and retaining independent contractor drivers across multiple markets. The role includes coaching and developing three direct reports, setting recruiting priorities based on validated driver demand, and stepping into frontline recruiting and driver-support work when needed. The supervisor travels regularly to company markets, including Phoenix, Las Vegas, Tucson, Kansas City, and new markets as the business grows. The supervisor improves driver recruitment, activation, engagement, and retention through data analysis, firsthand evaluation of the driver experience, process improvements, and partnership with Operations. The role manages new and advanced driver orientation content and administration, coordinates client route orientations, audits market practices, resolves driver issues, oversees related vendors and platforms, and provides leadership with scorecards, risks, trends, and recommendations. The position is onsite and offers annual compensation of $65,000–$70,000 plus up to a $4,000 annual bonus paid quarterly.

Requirements

At least 5 years of relevant recruiting, staffing, workforce operations, orientation, or contractor-relations experience.
At least 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.

Nice To Haves

Experience in independent contractor, transportation, logistics, staffing, or field-workforce environments.
Experience with OpenForce or a comparable contractor settlement platform.
Experience with Indeed, Zoho Recruit/CRM, CXT, Zello, screening, surveys, or dashboards.
Experience in curriculum development, training, vendor management, or process governance.

Responsibilities

Lead, coach, and develop the Recruiting & Engagement team across multiple markets.
Set market priorities and sourcing strategies based on validated driver demand.
Set 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 carry out targeted action plans.
Manage driver sourcing projects tied to new customer onboarding, including strategy, work distribution, results monitoring, and additional sourcing efforts as needed.
Develop and maintain a department best-practices toolbox covering vehicle requirements, sourcing strategies, and market-specific recruiting practices.
Evaluate the driver experience firsthand, from finding advertisements through application, and identify ways to reduce friction.
Implement improvements to the driver experience, reduce preventable early loss, strengthen 90-day retention, and improve conversion through the driver journey.
Support frontline 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.
Resolve driver issues, including settlement escalations, platform access, support coordination, and workflow governance.
Oversee vendors and platforms supporting contractor sourcing, settlements, communication, and orientation, including Indeed, Open Force, CXT, Zello, and Zoho Recruit.
Provide leadership with scorecards, risks, trends, and data-driven performance recommendations.