Help Desk Support Lead

Skyward; United States; Hybrid; USD 90,000 - 130,000; Full time

Benefits offered by this job

Medical/Dental/Vision insurance

15 days paid leave

401K with 4% employer contribution

Company laptop provided

Professional development $5,000/year

Life and disability insurance

HSA and FSA

Job summary

Skyward, a government contractor based in Maryland, is seeking a Help Desk Support Lead to calm frustrated users and keep a high-velocity support queue running smoothly for CMS enterprise AI services.

You will mentor staff, own the queue, craft playbooks, and relay leadership feedback to product and engineering. Skyward emphasizes remote-friendly, flexible hours and a culture focused on integrity and excellence.

Qualifications

• 5+ years in IT support with team-lead or supervisory experience.
• Exceptional communication skills, capable of supporting executives.
• Calm, unflappable demeanor in high-stress situations.
• Ability to research and resolve technically complex issues.
• Must be able to obtain and maintain a Public Trust security clearance.

Responsibilities

• Lead CMS’s enterprise AI services support for high-profile users.
• Own the support queue, set response quality, and maintain rhythm.
• Provide white-glove support to CMS stakeholders, up to the Administrator’s office.
• Mentor staff, build playbooks, raise team performance.
• Channel leadership feedback to product, AI, and engineering teams.
• Maintain SOPs, knowledge base, and post-deployment tests.

Skills

IT support

Team lead

Executive communication

Problem solving

Public Trust clearance

Education

Bachelor's degree

Job description

We are Skyward.
That is, a love for people, for improvement, for human advancement through information technology. We are a people-centered business with a desire to serve others. We are diverse and unified; creative and collaborative; a collection of complementary, not competing talents. And though on the surface we remain relaxed, beneath, a torrent of energy links us to our civic tech mission.

We are Skyward.
That is, a love for people, for improvement, for human advancement through information technology. We are a people-centered business with a desire to serve others. We are diverse and unified; creative and collaborative; a collection of complementary, not competing talents. And though on the surface we remain relaxed, beneath, a torrent of energy links us to our civic tech mission.
We stand by our values, and we won’t compromise on any of them.
Integrity: We’re conscientious, intentional, and empathetic. Our words and actions align. That’s our character. Please don’t ask us to play another part, we’re poor actors.
Compassionate: If we may borrow a quote from Theodore Roosevelt: “No one cares how much you know until they know how much you care.” Because our team is thoughtful and supportive, caring deeply for each other, our clients, and our work, this comes naturally.
Inquisitive: We remain students by failing openly and turning lessons into solutions.
Unconventional: For us, life isn’t what happens outside of work. Work happens inside of life and our culture erases the line often dividing the two.
Authentic: Made possible only because we embody the values listed above. We’re relaxed and fun yet intensely curious and driven. Team members are placed with thought, care, and precision to ensure that Trust, Truth, and Transparency continue to represent our brand.
Because of that, we continue Onward, Upward, and Skyward.

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?

Come join us if you're motivated to learn from others, to learn from mistakes, to be part of a future‑looking and growth-oriented team.

Let's go Skyward together.

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

And now the important part. What we offer you:

• 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. Who says government work can’t be exciting!

At Skyward, we support flexible working hours and remote opportunities to help maintain a healthy work‑life balance for all employees.

Offers of employment with Skyward are contingent upon acceptable results of a background investigation.

Applicants must have the ability to obtain and maintain a Public Trust security clearance due to the nature of our work as a government contractor.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.

We believe great work deserves great pay. That’s why we ensure our compensation is not only competitive but also fair and transparent, as required by Maryland law. Expect a salary that matches your skills, experience, and the value you bring to the table - because you’re worth it!