Site Lead

Drive Sally•Chicago, IL

4h•$75,000 - $95,000•Onsite

About The Position

Sally’s mission is to be the most trusted vehicle and service provider for professional drivers. We operate a large fleet of vehicles that we provide to rideshare, last mile, and taxi drivers on a flexible basis. We invest heavily in our technology and our people to deliver best-in-class service to our customers. The Site Lead is the next evolution from the Customer Support Lead role and is responsible for owning the full day-to-day performance of a Sally location, including operational execution, team leadership, and site-level results across customer experience and fleet readiness. This role owns site-level results by leading frontline and Customer Support teams, driving rental workflows, ensuring fleet compliance, and maintaining high service standards. The Site Lead acts as the operational backbone of the location and is accountable for both team performance and customer outcomes. Success in this role looks like high vehicle utilization, strong launch execution, fast resolution of customer issues, and a well-run site that consistently delivers a reliable, professional customer experience.

Requirements

1+ years in the rental car industry
3+ years of experience in operations, site management, office management, or customer support leadership.
Experience leading teams in fast-paced, customer-facing environments.
Strong organizational, communication, and problem-solving skills.
Comfort using data and reporting tools (e.g., Google Sheets) to guide decisions.
Ability to prioritize, adapt, and lead calmly under pressure.
Flexibility to work varied schedules as business needs require.
Willingness to travel as needed.

Responsibilities

Own day-to-day site operations, ensuring efficient, safe, and compliant execution of rental activities.
Lead rental workflows including vehicle launches, returns, swaps, repossessions, impounds, and customer inquiries.
Monitor and drive site-level operational metrics, including utilization rate, launch performance, and customer satisfaction.
Step into operational gaps as needed, resolving staffing, workflow, or customer issues in real time.
Act as escalation point for both employees and customers, resolving complex issues professionally and efficiently.
Deliver a high-quality customer experience across phone, text, email, and in-person interactions.
Partner closely with maintenance and garage teams to ensure vehicle readiness and minimize downtime.
Own fleet compliance at the site level, including registrations, insurance, inspections, and city sticker renewals.
Oversee office operations, including facilities coordination, supplies and inventory management, vendor and landlord relationships, compliance postings, and maintaining a safe and organized workspace.
Identify opportunities for process improvement and support site-level operational initiatives.
Build and maintain strong working relationships with co-located Fleet teams.
Hire, train, and develop a high-performing team through clear expectations, ongoing coaching, performance reviews, and a strong culture of accountability and execution.
Own team productivity and health by managing staffing plans, onboarding, PTO planning, and retention—ensuring the team stays engaged, supported, and consistently delivering results.