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Executive Support Analyst (C-Level/Owner Support)

Insight Global

Rosemont, ILContractSeen todaySeen in employer's feed today

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At a glance

Compensation
No compensation found
Location
Rosemont, IL
Schedule
Contract
Work Authorization
Not specified

Olive lists jobs from US employers, including remote roles you can work from the United States.

Job overview

Insight Global is seeking an experienced IT Executive Support Analyst to provide dedicated, discreet technical support to approximately 160 high-priority users, including owners and C-suite executives. The role combines in-person and remote support across Mac and Windows environments, devices, Microsoft technologies, executive residences, and meetings. The contractor begins onsite five days per week; a hybrid schedule may be possible after conversion but is not guaranteed.

Skills & qualifications

RequiredNice to have

Skills

Executive SupportVIP SupportWhite-Glove SupportMac SupportWindows SupportOperating SystemsEnd-User TechnologyMobile Device SupportDevice EnrollmentMicrosoft 365OutlookMicrosoft TeamsMicrosoft OfficeAzureEntra IDActive DirectoryIn-Person Technical SupportRemote Technical SupportWritten CommunicationVerbal CommunicationExecutive PresenceComposureSolution OrientationProfessionalismDiscretionSound JudgmentAttention to DetailIndependent WorkIssue Ownership

Qualifications

5+ Years Executive Support ExperienceC-Suite and Owner Support ExperienceOnsite Rosemont Availability

Full job description

Job Description

seeking an experienced IT Executive Support Analyst to provide dedicated, white-glove technical support to approximately 160 high-priority users. The user population includes company owners, family members, spouses and children, family-office personnel, C-suite executives, executive administrators, aviation and flight-coordination teams, clients, maintenance personnel, and household staff. This is not a traditional help desk position. The person will work directly with high-profile users who expect responsive, professional, and discreet support. The right candidate must be equally strong technically and interpersonally. They need to communicate clearly, remain composed under pressure, and confidently own issues through resolution. The position is approximately: 40% in-person support 60% remote support The contractor will begin onsite five days per week to learn the environment, build relationships, and provide direct support. There may be an opportunity for a hybrid schedule after conversion, but this should not be presented as guaranteed. Responsibilities Provide white-glove technical support to owners, family members, C-suite executives, executive administrators, family-office personnel, aviation teams, and other high-priority users. Deliver approximately 40% in-person support and 60% remote support. Troubleshoot and resolve issues across both Mac and Windows environments. Support desktops, laptops, mobile phones, tablets, printers, peripherals, operating systems, and Microsoft applications. Set up and configure new phones, iPads, laptops, and other devices. Ensure devices are properly enrolled, secured, and configured for corporate access. Troubleshoot access issues involving internal applications, training platforms, payroll or W-2 information, and other business systems. Support Microsoft 365, Azure, Entra ID, Active Directory, and related Microsoft technologies. Troubleshoot home networking, internet connectivity, and technology issues associated with executive residences. Provide support for audiovisual systems, conferencing technology, presentations, executive meetings, and special events. Coordinate with Comcast, technology vendors, and other third-party providers supporting residential or executive environments. Escalate issues to networking, infrastructure, security, identity, or application teams when necessary. Document, manage, and track support requests through ServiceNow. Prioritize successful issue resolution and the executive experience over ticket-volume metrics. Maintain strict confidentiality when handling sensitive personal, financial, executive, and business information. Provide a polished, calm, and customer-focused experience even when users are frustrated or operating under time pressure.

Skills and Requirements

5–7+ years of Executive support, VIP support, and/or white-glove support experience with C-levels/owners of the business Significant experience directly supporting C-suite executives, senior leadership, owners, family-office users, or other high-profile stakeholders. Strong hands-on experience supporting both Mac and Windows environments (Mac and PC support experience is required. Candidates who are heavily experienced in only one environment will not be the right fit) Experience troubleshooting operating systems, laptops, desktops, printers, peripherals, and common end-user technology. Strong mobile-device support experience, including iPhones, iPads, device setup, enrollment, configuration, and application access. Experience supporting Microsoft technologies, including Microsoft 365, Outlook, Teams, and Office applications. Experience working with Azure, Entra ID, and Active Directory. Ability to provide both in-person and remote technical support. Excellent written and verbal communication skills. Strong executive presence with the ability to explain technical issues clearly and professionally. Ability to remain calm, composed, and solution-oriented when supporting demanding or frustrated users. High level of professionalism, discretion, sound judgment, and attention to detail. Ability to work independently and take ownership of an issue through resolution. Willingness and ability to work onsite in Rosemont five days per week.

We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal employment opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment without regard to race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or the recruiting process, please send a request to [email protected].

How this job compares

Set against the 2,922 open IT Support jobs on Olive Jobs, counted October 29, 2026.

Pay
  • This postingNot listed
  • Illinois median$70–90K/yr30 salary ranges
  • Illinois median$25–30/hr32 hourly ranges
Openings
Olive Jobs lists 75 open IT Support jobs in Illinois and 2,922 across the US. 2% of them nationwide are listed as remote or flexible.
Experience
This posting asks for at least 5 years of experience — more than three in four IT Support postings that state a minimum ask for (median 2 years, across 2,041 postings).
Education
525 of the 2,922 open IT Support jobs (18%) ask for a bachelor's degree or higher.

Counted across the open, public US postings on Olive Jobs on October 29, 2026. Pay medians are the middle values of the low ends and of the high ends of postings that list both ends of a range in the same cadence (a yearly salary or an hourly rate); a range's midpoint is halfway between its ends. Pay and experience figures resting on fewer than 20 postings are left out.

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