We need a 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.
Come join us if you're motivated to learn from others, to learn from mistakes, to be part of a future-looking and growth-oriented team.
Let's go Skyward together.
What you’ll do:
- 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.
What we’d like you to have:
- 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.
What would blow us away:
- 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.
And now the important part. What we offer you:
- Medical, dental, vision insurance
- 15 days of paid leave
- 7 days of sick leave
- 2 days bereavement leave
- 11 paid Federal holidays
- Up to 40 hours for jury duty
- 401K with 4% employer contribution (and no vesting period)
- Up to 4 weeks of paid paternity and maternity leave
- Company provided laptop
- $5,000 per year for professional development
- $600 per year for technical supplies and equipment
- $2,000 referral bonus
- Life and disability insurance
- HSA and FSA
- Legal Shield and ID Shield Voluntary Benefits
- Opportunity to work in a collaborative, motivated team focused on modernizing government services with cutting-edge technology and innovative solutions. Who says government work can’t be exciting!
Skills Required
- 2+ years delivering customer service in an IT help desk or technical support environment
- Strong communication and interpersonal skills
- Professionalism and discretion
- Calm, friendly, and unflappable demeanor under pressure
- Curiosity about AI and helping people use new technology
- Ability to obtain and maintain a Public Trust security clearance
- Experience supporting AI/ML, chatbot, or LLM-based tools
- Experience with the ServiceNow platform
- Experience supporting CMS or another federal agency
What We Do
Skyward IT Solutions, LLC is a technology services provider specializing in AI-driven government services and digital modernization for federal and public sector operations. Founded in 2013, the company delivers secure, scalable, and user-centered solutions including custom AI agents, cloud engineering, and agile software development, focusing on improving service delivery and operational efficiency for agencies such as CMS and the SBA.
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