Help Desk Support Lead

Skyward IT Solutions•Rockville, MD

13d•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. Our values are integrity, compassion, inquisitiveness, unconventionality, and authenticity. We are looking for a Help Desk Support Lead who can calm a frustrated user and a frazzled team, take pride in a support queue that runs efficiently, and enjoys making people's day smoother. This role involves leading support for CMS’s enterprise AI services, owning the support queue, providing white-glove support to CMS stakeholders, mentoring support staff, channeling feedback to product teams, and maintaining SOPs and knowledge base articles.

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.