Remote AI Help Desk Analyst for Enterprise Tools

Skyward IT Solutions, LLC; United States; Remote; USD 60,000 - 72,000; Full time

Benefits offered by this job

Medical, dental, vision insurance

15 days paid leave

7 days sick leave

2 days bereavement leave

11 federal holidays

401K with 4% employer contribution

Up to 4 weeks paid paternity/maternity

Company laptop

$5,000/year for professional dev

$600/year for supplies

$2,000 referral bonus

Life and disability insurance

HSA and FSA

Voluntary benefits: Legal Shield & ID 

Remote-friendly working

Job summary

Skyward IT Solutions, LLC is seeking a Help Desk Support Analyst to provide friendly Tier 1–2 support for CMS’s enterprise AI tools. You’ll assist users via chat, email, phone, video, and the service desk portal, making complex AI feel simple and approachable.

Ideal candidates are calm under pressure with strong communication skills, and a genuine curiosity about AI. This remote-friendly role supports flexible hours and a dynamic government-facing environment.

Qualifications

• 2+ years delivering top-notch customer service in an IT help desk or technical support environment.
• Strong communication and people skills, with professionalism and discretion.
• A calm, friendly demeanor under pressure.
• Genuine curiosity about AI and helping people use new technology with confidence.

Responsibilities

• Provide Tier 1–2 support for CMS’s enterprise AI tools to stakeholders across the agency — warmly, quickly, and professionally.
• Meet users where they are via chat, email, phone, video, and the service desk portal.
• Explain usage and guide users to make AI feel simple and effective.
• Troubleshoot software and AI-tool issues with discretion and a calm head.
• Capture user feedback and relay to product/engineering teams.
• Maintain SOPs and knowledge base articles; assist with UAT and smoke tests.

Skills

Customer service

IT help desk

Communication

Discretion under pressure

Tools

ServiceNow

Job description

Skyward IT Solutions, LLC is seeking a Help Desk Support Analyst to provide friendly Tier 1–2 support for CMS’s enterprise AI tools. You’ll assist users via chat, email, phone, video, and the service desk portal, making complex AI feel simple and approachable.

Ideal candidates are calm under pressure with strong communication skills, and a genuine curiosity about AI. This remote-friendly role supports flexible hours and a dynamic government-facing environment.