Job Description
Executive Support IT Specialist
Cleveland OR Richfield, OH (Onsite, with oversight of a multi-regional team) We are seeking an experienced, customer-driven Executive Support Specialist to lead our geographically dispersed IT support team. In this role you'll manage a local support staff and provide leadership to a remote team across multiple U.S. locations. This position plays a critical role in ensuring high-quality, white-glove support to C-level executives, executive assistants, and other high-visibility stakeholders.
This is a true player/coach position with a 50/50 split between hands-on support and team management. You will be directly responsible for overseeing daily ticketing operations, managing vendors and resources, introducing and optimizing a single service number queue, and distributing support responsibilities among a team of 6–8 technicians. The environment supports approximately 1,400 users and demands a high level of organization, responsiveness, and leadership maturity.
We're looking for someone who not only brings strong technical skills but who also excels in people management and communication. The ideal candidate is an extroverted leader who thrives in fast-paced settings, can manage diverse personalities, and remains composed and solutions-focused in high-pressure executive support situations.
Key Responsibilities: - Lead and mentor a geographically dispersed team of desktop support technicians
- Manage vendor relationships, resource planning, and out-tasked IT functions (Level 1 help desk, imaging and deployment, field services)
- Establish and manage a unified service desk number and ticket queue
- Ensure timely and effective resolution of support requests, with a customer-first mindset
- Provide high-touch executive and conference support at the Cleveland HQ
- Actively contribute to shaping and building the future state of the IT support organization
- Serve as escalation point for high-impact support issues and sensitive user interactions
- Balance team management responsibilities with hands-on support as needed (50/50 role)
Required Skills & Experience: - Proven experience leading desktop support teams across multiple regions or locations
- Demonstrated ability to manage support operations for both enterprise users and senior leadership
- Strong communication skills and ability to defuse tense situations diplomatically
- Hands-on technical support expertise, including troubleshooting Windows OS, Microsoft 365, hardware, and networking issues
- Familiarity with ITIL or other structured incident management frameworks
- Experience with support tools including ticketing systems, remote support platforms, and asset tracking
- Track record of driving process improvement, introducing new tools, and enhancing end-user experience
- Customer-obsessed attitude with an ability to build rapport across all levels of an organization
- Capable of managing diverse personalities, from C-level executives to junior contributors
- Experience shaping or scaling an internal IT department is a strong plus
Preferred Traits: - Extroverted and approachable leadership style
- White glove customer service
- High emotional intelligence and people management instincts
- Resourceful, adaptable, and forward-thinking in both strategy and execution
Job Tags
Full time, Local area,