Help Desk Support Lead

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🦀 Maryland – Remote

🦀 Maryland – Remote

💵 $78k - $95k / year

⏰ Full Time

🟠 Senior

💻 IT Support

🦅 H1B Visa Sponsor

This company has sponsored H1B visas in the past.

👻 Ghost score 2%

What it means: how likely this posting is sitting open without active hiring.How to read it: 60% or higher means we think this is a ghost. Lower scores are less of a worry.How we score it: age, reposts, open roles vs team size, how fast jobs close, and whether pay is listed.Fine print: an estimate from public data, not a judgment of the company. Real jobs can score high, so treat it as a hint, not a fact.

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Skyward

WebsiteLinkedInAll Job Openings

51 - 200 employees

🤖 Artificial Intelligence

🏛️ Government

Artificial Intelligence • Government • Technology

Skyward is a Maryland-based digital services organization that specializes in AI/ML, Agile DevSecOps, and Data Science, serving as a trusted Federal partner. With a mission to serve the American people, Skyward delivers agile, user-centered, and scalable solutions for mission-critical programs, working closely with Federal Government allies. The company prides itself on being a member of the Digital Services Coalition and focuses on advancing innovation and excellence in government technology. Skyward is dedicated to transforming AI possibilities into impactful realities and is committed to improving customer experiences and software delivery processes. The company has significantly grown its workforce and impacts millions of Americans and small businesses through its services.

📋 Description

• 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 • Support UAT and post-deployment smoke testing

🎯 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 • Offers of employment contingent upon acceptable results of a background investigation • Experience supporting AI/ML, chatbot, or LLM-based tools (preferred) • Experience providing executive or VIP-level support (preferred) • Previous experience supporting CMS or another federal agency (preferred)

🏖️ 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 • Flexible working hours • Remote opportunities • Opportunity to work in a collaborative, motivated team focused on modernizing government services with cutting-edge technology and innovative solutions