[Hiring] Help Desk Support Lead @Skyward IT Solutions

Role Description

We need a Help Desk Support Lead. Are you the person who can calm a frustrated user and a frazzled team in the same five minutes? Do you take real pride in a support queue that runs like a well-oiled machine - fast, friendly, and never dropping the ball? If you love running a support operation that makes people’s day smoother, then please apply.

• 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.

Qualifications

• 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.

Requirements

• Experience supporting AI/ML, chatbot, or LLM-based tools.
• Experience providing executive or VIP-level support.
• Previous experience supporting CMS or another federal agency.

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.
• $78,000 - $95,000 a year
• Flexible working hours and remote opportunities to help maintain a healthy work-life balance for all employees.