Head of Software Development

  • Des Plaines, IL - United States
  • Full-time

The Company


Focused on your fleet and driving optimal results to your business.Wheels is the world’s most experienced automotive fleet leasing and management company, and a trusted industry leader. We provide organizations around the world with company cars and trucks along with state-of-the-art services and support.

  • We’re the largest privately held fleet management company. In fact, with more than $1.6 billion in annual sales and nearly $3 billion in assets, we’re one of North America’s largest private companies in any industry.
  • Our single line of business gives us a dedicated focus. Fleet leasing and management are all we do, so we’re able to commit 100% of our resources to delivering innovative fleet solutions for our clients.
  • Find us around the corner and around the world. With more than 300,000 vehicles under management throughout North America and more than 1.6 million globally, chances are you see a Wheels vehicle on the road every day.
  • We service some of the world’s best-known companies. Our client portfolio includes dozens of Fortune 500 businesses and other leading organizations who view their sales or service fleets as a strategic business tool.

The Head of Software Development is accountable to drive large-scale, high-profile, strategic and operational initiatives inside the technology organization to increase operational efficiency, improve existing service quality/delivery and create new service models in support of our client’s goals while creating competitive differentiation for Wheels in our industry by effectively managing a highly skilled workforce in a culturally diverse environment.

This role is expected to develop organization wide procedures for the Software Development team to develop systems that align with the product management and IT architecture goals. Additionally, this role is responsible for the strategic development of software development plans and objectives that support the architecture, user experience, design, development, implementation and support of innovative software products using a strong technical skill-set and creativity.



  • Responsible for technology leadership of the group. Defines the technological vision and roadmap for the software development department. Ensuring that the development group is always at the cutting edge of technology and user experience. Assign research goals and technology targets for teams in the department.
  • Define team structure and leader responsibilities according to the department needs. Assign available positions to the different teams and define new roles and teams when needed.
  • Responsible for financial management of salary, T&E, vendor/contract services, software acquisition and maintenance, and project budgets.
  • Responsible for the deliverables of the software development department and their quality. Define targets, technological guidelines and quality standards for the managers in the group. Review execution, quality and technology/usability standard adherence of the deliverables of the different teams and provide active coaching for the managers in the group.
  • Lead the software development management team. Define personal goals and objectives for senior team leaders. Provide technological and management skill guidance to the different managers in the team. Define the management values and best practices for the software development management team
  • Initiates and maintains positive relationships with the team and other members of the company; facilitates relationships with all cross-functional team members while working on joint projects.
  • Plans for and manages the recruitment, interviewing, selection, orientation and continued training and education of staff. Evaluates the work of individuals assigned to the departments supervised.
  • Key member of the IT and Company Leadership. Key contributor to the product vision and roadmaps. Contribute to strategic decisions for the identification, evaluation and selection of technologies to improve the speed of development, quality and innovation.
  • Manage outsourced, contract and software vendor relationships to maximize value and quality
  • Maintain responsive and accountable services, with rapid response to customer requests and appropriate follow-through. Manage internal and external customer expectations and anticipate their needs; continually review existing services in light of changing company strategies; and design appropriate new services, anticipating rapid changes in information technology.
  • The overall performance of the holder of this position is measured by the performance of the software development department - Deliverables being provided on schedule and in high quality with an intuitive user experience. Additional aspects are: the innovative solutions that are developed in the department, the improvements in the efficiency of the department’s work, the use of leading edge technologies, and the improvement in the professional level of the work force in the department achieved either by internal development plans or recruiting.
  • Other duties as assigned.


Supervisory Responsibilities

  • Supervise a total team of 50 plus employees (8 in leadership/managerial roles) and approximately 40 - 50 consultants
  • Supervise a geographically dispersed team primarily in Des Plaines, IL and India
  • Manage an annual budget around $15M

QUALIFICATIONS To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. The requirements listed below are representative of the knowledge, skill, and/or ability required. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

Professional Knowledge: Effective leadership principles, deep expertise in the areas of interpersonal relations, planning, collaboration, and issue analysis; working knowledge of current technologies, enterprise systems and their applications; network systems and applications; relational data base systems; understanding of business processes and operations; understanding of the possibilities and limits of technologies; budgeting and resource management processes; operational effectiveness principles; decision making and analytical tools.

Professional Skills: Excellent communication, oral, listening, and written; public speaking; assessment of needs; strategic thinking; organization, supervision, staff education and training, project management, report writing, complex problem solving, credibility, team player, standard mathematic calculations, delegation, statistical concepts and their applications, and interpretative analysis.

Professional Abilities: Able to communicate well with and at all levels of the company; form alliances and relationships with business partners; work collaboratively and effectively with all employees; agility to stay flexible and open at all times; manage resources when demand exceeds availability; ethical in all matters; network with others within and outside of company; able to cross over the artificial boundaries between silos in the organization; and advocate for the application of technology. Demonstrated ability to create an environment which provides superior and innovative software development and technical support.


Minimum Requirements


  • BS in Computer Science or related field or MBA preferred
  • 10+ years of proven experience in managing teams and senior managers
  • Proven experience in building and motivating teams
  • Ability to work independently with effective time management in a fast paced, deadline driven environment
  • Hand-on software development background and experience
  • Experience managing a team to build and support mostly custom software using modern technologies
  • Knowledge of IT infrastructure/environment concepts like virtualization, cloud, containers, load balancers, network design, security, release management, etc.
  • Experience in one or more Agile methodology
  • Excellent soft skills
  • Ability to work across teams and with remote teams


Desired Qualifications

  • Deep knowledge of Agile methodologies
  • Development background in Web and Mobile preferred
  • Deep knowledge with advance DevOps techniques
  • Managing custom software develop using Microsoft centric technologies including C#, SQL Server, Web Services, and Xamarin plus AngularJS, Qlik, etc.
  • Knowledge of emerging low-code platforms like Force.com, OutSystems, Mendix, etc.

PHYSICAL DEMANDS The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

WORK ENVIRONMENT The work environment characteristics described here are representative of those an employee encounters while performing the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

ID: 2017-2310

External Company Name: Wheels, Inc.


Seniority Level

Mid-Senior level


  • Automotive
  • Management Consulting
  • Transportation/Trucking/Railroad

Employment Type


Job Functions

  • Engineering
  • Information Technology


Disclaimer: This job offer was originally posted on LinkedIn.