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Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md). --- # Help Desk Support Analyst - **Company:** Skyward Inc - **Location:** United States (Remote available) - **Experience:** Experienced - **Contract:** Permanent contract - **Skills:** Artificial Intelligence, Smoke Testing, Chatbots, Large Language Models, Servicenow - **Published:** September 12, 2026 - **Apply:** https://startup.jobs/help-desk-support-analyst-skyward-10025011 ## About the Role * 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. ## Description 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. 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. ## Related Videos - [Chatbots are going to destroy infrastructures and your cloud bills](https://www.wearedevelopers.com/videos/1130-chatbots-are-going-to-destroy-infrastructures-and-your-cloud-bills) - [Applying Agile Principles to Incident Management ](https://www.wearedevelopers.com/videos/101-applying-agile-principles-to-incident-management) - [Implementing smoke testing and proactive monitoring in production](https://www.wearedevelopers.com/videos/171-implementing-smoke-testing-and-proactive-monitoring-in-production) - [Agentic employees in world's most downloaded FinTech app](https://www.wearedevelopers.com/videos/100123-agentic-employees-in-world-s-most-downloaded-fintech-app) - [Integrate your Cognitive Assistant with 3rd-party DBs and software](https://www.wearedevelopers.com/videos/249-integrate-your-cognitive-assistant-with-3rd-party-dbs-and-software) - [The AI-Ready Workforce: Upskilling Lessons from the Real World](https://www.wearedevelopers.com/videos/100280-the-ai-ready-workforce-upskilling-lessons-from-the-real-world) ## Related Articles - [How to Become an AI Engineer](https://www.wearedevelopers.com/magazine/331-how-to-become-an-ai-engineer) - [Got AI ideas but no money? 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