Help Desk Support Lead

What you'll do:

• Lead support for CMS’s enterprise AI services, keeping high-profile users productive and happy.
• Own the support queue, set the standard for response and quality, and keep the team’s rhythm tight.
• Provide white-glove support to CMS stakeholders, up to the Administrator’s office, with polish and discretion.
• Mentor support staff, build playbooks, and raise everyone’s game.
• Channel feedback from leadership back to the product, AI, and engineering teams.
• Maintain SOPs and knowledge base articles and support UAT and post-deployment smoke testing.

What we’d like you to have:

• A bachelor’s degree and 5+ years in IT support, with team-lead or supervisory experience.
• Exceptional communication and people skills, with the polish to support senior executives.
• A calm, unflappable demeanor in high-stress, high-visibility situations.
• The ability to research and resolve technically complex issues.
• The ability to obtain and maintain a Public Trust security clearance.

What would blow us away:

• Experience supporting AI/ML, chatbot, or LLM-based tools.
• Experience providing executive or VIP-level support.
• 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.