Help Desk Support Analyst

Skyward IT Solutions•Rockville, MD

15h•Hybrid

About The Position

We are Skyward, a people-centered business with a desire to serve others, driven by a love for people, improvement, and human advancement through information technology. We are diverse and unified, creative and collaborative, with a torrent of energy linked to our civic tech mission. We stand by our values: Integrity, Compassionate, Inquisitive, Unconventional, and Authentic. We are looking for a Help Desk Support Analyst who is the "go-to tech person" in their group, can make technology feel easy, stays calm under pressure, and takes pride in making someone’s day smoother. This role offers white-glove support with a front-row seat to the future of AI at CMS. If you have the patience of a saint and a genuine love for helping people, we encourage you to apply. Let’s go Skyward together.

Requirements

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.

Nice To Haves

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

Responsibilities

Be the friendly face of AI, providing Tier 1-2 support for CMS’s enterprise AI tools to stakeholders across the agency warmly, quickly, and professionally.
Support users via chat, email, phone, video, and the service desk portal.
Make sophisticated AI feel simple by answering questions, guiding usage, and turning user inquiries into positive outcomes.
Diagnose and resolve software and AI-tool issues with discretion and a calm head.
Capture user feedback and route it back to the product and engineering teams.
Maintain SOPs and knowledge base articles.
Support UAT and smoke testing.

Benefits

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.
Flexible working hours
Remote opportunities