Vice President of Operations

Sasser, Inc. • Oak Brook, IL

1d • Onsite

About The Position

Sasser is a transportation asset services and management company, recognized as one of the Best Places to Work in Chicago. Its subsidiary, Union Leasing, is a premier fleet leasing and management solutions provider with over 60 years of experience. The Vice President of Operations will lead all aspects of Union Leasing’s operations, driving operational performance, product innovation, and vendor partnerships. This role focuses on steering the end-to-end lifecycle of fleet management solutions, optimizing efficiency, and enhancing service delivery. The leader will define the strategic vision for operational excellence, champion innovation in products and services, and elevate the organization’s analytics capabilities to drive data-driven decisions. As a key member of the Union Leasing Leadership Team, this position is central to shaping organizational strategy and growth, with an emphasis on talent development and fostering a culture of urgency and accountability to deliver industry-leading service and value.

Requirements

• Bachelor’s degree in business administration, operations management, engineering, or other related field.
• 10+ years of leadership experience in fleet management, rental, automotive, or asset-intensive operations with a strong understanding of process improvement.
• Background in technology leadership, successful technology projects.
• Demonstrated ability to lead cross-functional teams in a matrixed environment.
• Results driven, able to focus on organizational growth and financial performance.
• Strong attention to detail, highly analytical, capable of turning insights into action plans.
• A strong sense of urgency and a willingness to do what it takes to support customer needs.
• Proficiency in Microsoft Office Suite (specifically Excel and Word).
• Outstanding communication skills, both verbal and written.
• Excellent analytical skills, process improvement mindset, experience analyzing large volumes of data.
• Entrepreneurial mindset with a roll up your sleeves attitude, not afraid to dig into the details.
• Ability, credibility and experience to autonomously direct and lead negotiations, influencing outcomes with vendors and suppliers.
• Demonstrated ability to influence and inspire through persuasion, negotiation, and relationship building.
• A high level of personal skill and experience making formal, persuasive presentations, effectively supporting and articulating the strategic positioning of the business, with the ability to work effectively with people at all levels of the organization or industry.
• Ability to independently drive projects to completion, while also functioning effectively in a team environment.

Nice To Haves

• Advanced degree preferred.

Responsibilities

• Provide overall leadership and direction for all Operating departments, including Procurement, Remarketing, Maintenance & Fuel, and Licensing, Compliance & Safety.
• Establish and enhance performance metrics to ensure data driven, efficient day to day operations.
• Drive continuous improvement in operational processes, delivering measurable gains in efficiency, service quality, and cost performance.
• Define system and automation requirements; partner with IT and senior leadership to recommend and implement technology investments that improve service delivery and customer experience.
• Lead the development and enhancement of revenue generating products and services, including innovation, optimization, and execution of new product opportunities.
• Strengthen vendor partnerships where strategically and financially beneficial, ensuring Union Leasing’s interests are protected and aligned with profitability targets.
• Oversee vendor negotiations to secure favorable terms, operational support, and financial value.
• Serve as the strategic leader for Operations, ensuring the organization has a clear, actionable strategy and that progress is made against it.
• Develop and execute strategies to enhance profitability, operational efficiency, and alignment with the company’s broader business objectives.
• Act as the lead executor of enterprise-wide strategic initiatives, working collaboratively with executive leadership to shape and implement organizational direction.
• Identify opportunities to improve products and services through partnerships, investments, or M&A activities.
• Lead initiatives to automate and streamline processes in partnership with Information Technology.
• Provide oversight and leadership for business transformation efforts, ensuring successful execution and alignment with strategic priorities.
• Advance Union Leasing’s analytics capabilities across customer, operational, and financial domains to support a fully data driven organization.
• Strengthen reporting, analytics adoption, and insights delivery to improve decision making at all levels.
• Harness telematics and real time data to enhance fleet visibility, utilization, safety, performance, and cost control.
• Leverage customer behavior analytics—including mileage, driver behavior, maintenance activity, alerts, and cost trends—to provide actionable recommendations.
• Implement predictive analytics to anticipate maintenance needs, optimize lifecycle costs, and improve customer outcomes.
• Monitor and manage operating KPIs, ensuring performance insights translate into targeted action plans.
• Analyze pricing trends to ensure competitive vehicle pricing and maximize auction proceeds.
• Evaluate auction throughput and efficiency, recommending strategic adjustments as needed.
• Continually assess and upgrade talent across the Operations organization to ensure the right people are in the right roles.
• Develop deep organizational expertise regarding Union Leasing’s products, customer needs, and industry trends.
• Foster a culture of urgency, accountability, respect, process discipline, continuous improvement, and data driven decision making.
• Set clear expectations for performance and hold team members accountable through consistent leadership and feedback.
• Mentor and develop staff to build the next generation of operational leadership.
• Remain current on industry developments and emerging trends to inform strategy and operational best practices.
• Partner closely with Customer Experience and Sales to align operational capabilities, service features, and product innovation with customer needs.
• Work with Finance to support budgeting, cost control and profitability.
• Collaborate with Express 4x4 leadership to leverage vendor synergies, operational efficiencies, and shared best practices.
• Work closely with the VP of Operations at Express 4x4 to maximize the value of combined scale and operational alignment.
• Act to support the interests of the department and organization and to perform other duties as assigned to ensure the successful achievement of departmental and company objectives.

Benefits

• Comprehensive medical, dental, and vision insurance plans, including HSA and FSA accounts with employer contributions toward HSA
• 100% Company-paid disability and life insurance plans
• 401K plan with company match PLUS additional end-of-year funding
• Paid vacation time (tiered based on tenure), as well as personal time, sick days and summer half days for certain roles
• 10 paid holidays annually
• Paid parental leave for new parents, as well as a monetary gift towards a 529 education account
• Confidential Employee Assistance Program
• Training and tuition reimbursement
• Community service opportunities, charity match opportunities, employee recognition programs, and many celebrations!

What This Job Offers

• Job Type: Full-time
• Career Level: Executive