Help Desk Support Lead

Skyward IT Solutions, LLC • Rockville, MD

14d • $78,000 - $95,000 • Hybrid

About The Position

We are Skyward, a people-centered business driven by a love for people, improvement, and human advancement through information technology. We are a diverse, unified, creative, and collaborative team unified by a civic tech mission. Our values of Integrity, Compassion, Inquisitiveness, Unconventionality, and Authenticity guide our actions. We are looking for a Help Desk Support Lead who can manage a support queue efficiently, provide excellent service to users, and lead a team. If you enjoy making people's day smoother through effective support operations, we encourage you to apply and join us at Skyward.

Requirements

• 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.

Nice To Haves

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

Responsibilities

• 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.

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.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level