We are Skyward.

That is, a love for people, for improvement, for human advancement through information technology. We are a people-centered business with a desire to serve others. We are diverse and unified; creative and collaborative; a collection of complementary, not competing talents. And though on the surface we remain relaxed, beneath, a torrent of energy links us to our civic tech mission.

We stand by our values, and we won’t compromise on any of them.

Integrity: We’re conscientious, intentional, and empathetic. Our words and actions align. That’s our character. Please don’t ask us to play another part, we’re poor actors.

Compassionate: If we may borrow a quote from Theodore Roosevelt: “No one cares how much you know until they know how much you care.” Because our team is thoughtful and supportive, caring deeply for each other, our clients, and our work, this comes naturally.

Inquisitive: We remain students by failing openly and turning lessons into solutions.

Unconventional: For us, life isn’t what happens outside of work. Work happens inside of life and our culture erases the line often dividing the two.

Authentic: Made possible only because we embody the values listed above. We’re relaxed and fun yet intensely curious and driven. Team members are placed with thought, care, and precision to ensure that Trust, Truth, and Transparency continue to represent our brand.

Because of that, we continue Onward, Upward, and Skyward.

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.

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!

$60,000 - $72,000 a year

We believe great work deserves great pay. That’s why we ensure our compensation is not only competitive but also fair and transparent, as required by Maryland law. Expect a salary that matches your skills, experience, and the value you bring to the table - because you’re worth it!

At Skyward, we support flexible working hours and remote opportunities to help maintain a healthy work-life balance for all employees.

Offers of employment with Skyward are contingent upon acceptable results of a background investigation.

Applicants must have the ability to obtain and maintain a Public Trust security clearance due to the nature of our work as a government contractor.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.