Job Description

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.

Overview:

We’re looking for a hands-on, people-first leader to drive Sally’s Chicago operations. This role is equal parts operational execution, team development, and strategic thinking. You’ll oversee a high-performing rental site, lead a team with clarity and urgency, and ensure we deliver reliable service while scaling responsibly.

This position demands grit, transparency, and sound judgment. You’ll be expected to lead when others aren’t around, bring structure to chaos, and prioritize in real time.

What you’ll do

• Own and exceed key operating and financial targets, including utilization rates, average rental rates, active rental days per unit, revenue, average wrench days, average hold days, and Google review scores.
• Lead rideshare operations, including customer interactions via email, text, phone, and in-person, as well as daily rental launches, returns, swaps, repossessions, and market-related inquiries.
• Coach, develop, and inspire frontline team members to execute with consistency and urgency
• Step into operational bottlenecks directly — whether it’s a workflow issue, customer escalation, or morale concern
• Liaise with garage facility operations to ensure vehicle readiness and efficient service turnaround times.
• Resolve customer issues promptly to ensure a positive customer support experience.
• Manage core administrative tasks: timecard approvals, PTO, performance conversations, hiring coordination
• Provide weekly reports to the management team.

What we look for

• Leadership & Execution
• Hands-on leader with a strong presence — earns respect by example
• Capable of inspiring and unifying teams around clear, metric-driven goals
• Calm under pressure, decisive, and fast-moving when needed
• High sense of urgency, follows through without letting details slip
• Character & Communication
• Genuine and transparent — doesn’t just say what people want to hear
• Gritty, reliable, and not afraid to get their hands dirty
• Communicates with clarity, respect, and motivation — even when delivering hard truths
• Strategic Thinking & Prioritization
• Exceptional judgment and critical thinking — can triage chaos into a plan
• Knows when to say no or push back — excellent risk management instincts
• Organized, structured, and able to keep moving pieces on track
• Purpose & Drive
• Seeks more than a job — looking to build skills, make an impact, and grow in responsibility
• Understands and can articulate what motivates them professionally

Qualifications

• 4+ years experience in operations, logistics, automotive, retail, or rental vehicles
• 3+ years in a people leadership role, ideally in a dynamic, fast-paced setting with up to 30 direct reports
• Bachelor’s degree preferred but not required if experience matches the need
• Strong proficiency in Google Sheets (data tracking, reporting, ops models)
• Proven ability to manage competing priorities and drive results

Benefits

• PTO
• Medical, Dental, and Vision benefits
• 401k
• Weekly team lunches

Compensation range: $95k - 145k

*Offer amounts within our ranges are based on skills, experience, relevant education or training, and other job-related factors. At Sally, we believe in making thoughtful decisions around compensation to ensure the growth and development of our employees. We want you to grow with us as our company grows!

Job Tags

Similar Jobs