Details for Position: Orl-VP SA

Vice President of Systems Administration

Location: Orlando

The Vice President of Systems Administration reports to our Chief Information Officer and is responsible for overseeing, developing and leading the strategic and tactical functions of the Systems Operations, Data Center Operations and internal IT operations, which includes small to complex initiatives. The position will develop and implement a flexible team that aligns with the organization’s business objectives and responsibilities.

The ideal candidate will have extensive experience in ecommerce operations including managing data centers, IT Systems, hardware and operating systems and databases as well as cloud computing and solid managerial and operational knowledge. The person hired into the role will develop the Company’s System Administrators Department.  The role will develop and manage a team and help Entertainment Benefits Group ensure agility and effectiveness as we grow.

The role ideally will be based in Orlando, FL. Some travel (less than 10%) is required and will mainly be to other offices or data centers. We will not consider remote candidates.


  • Define the System Administrator Department roles and build a team of Systems Administrators, Application Administrators and IT teams encompassing a mixture of on property, off property hosted, cloud based systems ranging from Linux, Windows, Azure, AWS and Managed Co-lo.
  • Create, plan and prioritize projects based on strategic objectives, cost/benefit considerations, risk, timing, capacity and interdependencies.
  • Develop standardized reporting to proactively and consistently report on status, and demand utilization.
  • Define, document and iterate on the key processes including roles, activities, artifacts, workflows and change processes. Continuously assess process to ensure new opportunities to increase effectiveness.
  • Develop team to deliver best practices (initiation to planning and execution) through information sharing and training throughout the organization.
  • Assure understanding and control of sync points and dependencies within the portfolio.
  • Tracking and reporting of budget vs plan.
  • Serves as primary contact for senior leadership on site operational status, objectives and issues.
  • Responsible for maintaining the systems budget, as well as department forecasts
  • Coach and mentor all team members to elevate consistent performance across the team.
  • Be a source for leaders that can be deployed into operational roles.
  • Ability to lead groups, employ strategic thinking, and direct involvement in delivering against targets
  • Understanding of software development and infrastructure project lifecycles
  • Ability to assess the impact of new project requirements on an existing team workload
  • Work with internal clients to understand their needs and assess business processes and workflows
  • Ensure 24/7 availability for the website, sertvers and internal systems such as phones.
  • Resolve and/or escalate issues in a timely fashion
  • Develop and distribute documentation to the community as needed
  • Complete special assignments necessary to support business strategy
  • Perform other related duties as required and assigned
  • Demonstrate behaviors which are aligned with the organization’s desired culture and values
  • Stay current on systems best practices and provide expertise


  • 10+ years of a proven record of successful Systems Administrations or IT Operations Management including managing large-scale initiatives through all phases of its life-cycle.
  • Hands on person, not an ivory tower type of person.
  • Hands-on experience in project/portfolio resource planning, reporting, prioritization, and resource budgeting.
  • Deep Understand in most of the following with topics along with expertise in several of the products in parentheses.
    • Operating Systems (e.g. Linux, Windows Server and Desktop, iOS)
    • Web Servers (e.g. Apache, Microsoft)
    • Databases (e.g. MS SQL, MySQL)
    • Programming Languages (e.g. PHP, C#)
    • Hardware (e.g. Servers, Switches, Firewalls, Load Balancers, PC’s)
    • 3rd party Applications (e.g. SalesForce, Jira, Confluence, Office 365)
    • Scripting Tools and Admin tools (e.g. PowerScript, Shell, Bash, SaltStack, Python)
    • Source Control (e.g. git, SVN)
    • DevOps (e.g. Jenkins, Puppet)
    • Development Methodologies (Agile, SAFe, Scrum, Kanban, Waterfall)
    • Telephone Systems (ShoreTel, Interactive Intelligence)
  • Ability to build an open environment
  • Ability to create, refine and implement process and methodology.
  • Able to function tactically but also strategically.
  • Proven ability to work with executive management as well as develop strong partnership with peers and other team members, influencing decision making at all levels without formal reporting structure authority.
  • Demonstrated leadership of multidiscipline, high-performance work teams/groups.
  • Good communication, and facilitation skills.
  • Ability to support executives to develop budgets for projects and activities.
  • Ability to lead change and then coach others in the acceptance and support of change.
  • Strong Vendor management and procurement experience.
  • Demonstrate ability to advance multiple priority assignments concurrently and within established deadlines.
  • Bachelor’s degree and/or Systems Administration certification(s) preferred but not required.

Other Information

The statements contained herein reflect general details as necessary to describe the principal functions of this job, the level of knowledge and skill typically required, and the scope of responsibility but should not be considered an all-inclusive listing of work requirements.