Remote Help Desk Lead for Enterprise AI Services

Skyward

United States

Hybrid

USD 90,000 - 130,000

Full time

11 days ago

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Benefits offered by this job

Medical/Dental/Vision insurance

15 days paid leave

401K with 4% employer contribution

Company laptop provided

Professional development $5,000/year

Life and disability insurance

HSA and FSA

Job summary

Skyward, a government contractor based in Maryland, is seeking a Help Desk Support Lead to calm frustrated users and keep a high-velocity support queue running smoothly for CMS enterprise AI services.

You will mentor staff, own the queue, craft playbooks, and relay leadership feedback to product and engineering. Skyward emphasizes remote-friendly, flexible hours and a culture focused on integrity and excellence.

Qualifications

5+ years in IT support with team-lead or supervisory experience.
Exceptional communication skills, capable of supporting executives.
Calm, unflappable demeanor in high-stress situations.
Ability to research and resolve technically complex issues.
Must be able to obtain and maintain a Public Trust security clearance.

Responsibilities

Lead CMS’s enterprise AI services support for high-profile users.
Own the support queue, set response quality, and maintain rhythm.
Provide white-glove support to CMS stakeholders, up to the Administrator’s office.
Mentor staff, build playbooks, raise team performance.
Channel leadership feedback to product, AI, and engineering teams.
Maintain SOPs, knowledge base, and post-deployment tests.