Help Desk Support Analyst

Are you the “go-to tech person” in your group of friends, the one who can make confusing technology feel easy without ever making anyone feel dumb for asking? Do you stay calm and friendly when the pressure’s on and take pride in making someone’s day a little smoother?

This is white-glove support with a front-row seat to the future of AI at CMS. If you’ve got the patience of a saint and a genuine love for helping people, please apply.

Let’s go Skyward together.

• Be the friendly face of AI. 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. Support them via chat, email, phone, video, and the service desk portal.
• Make sophisticated AI feel simple. Answer questions, guide usage, and turn “how does this work?” into “oh, that’s great.”
• Troubleshoot with grace. Diagnose and resolve software and AI-tool issues with discretion and a calm head.
• Be the voice of the user. Capture feedback and route it back to the product and engineering teams.
• Keep quality high. Maintain SOPs and knowledge base articles and support UAT and smoke testing.

• 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, unflappable demeanor under pressure.
• Genuine curiosity about AI and helping people use new technology with confidence.

• Experience supporting AI/ML, chatbot, or LLM-based tools.
• Experience with the ServiceNow platform.
• Previous experience supporting CMS or another federal agency.

Even if you don’t meet 100% of the qualifications, we encourage you to apply. At Skyward, we’re focused on hiring individuals with the right skills and passion to grow, not just checking off every box.