Help Desk Support Lead
Skyward IT Solutions, LLCRockville, MD
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Overview
Schedule
Flexible-schedule
Full-time
Career level
Director
Remote
On-site
Benefits
Health Insurance
Dental Insurance
Vision Insurance
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 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? If you love running a support operation that makes people’s day smoother, then please apply.
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 demeanorin high-stress, high-visibility situations.
- The ability to research and resolvetechnically 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 CMSor another federal agency.
Even if you don’t meet 100% of the qualifications, we encourage you to apply. At Skyward, we’re focused on hiring individuals with the right skills and passion to grow, not just checking off every box.
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!
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!
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.
Automate your job search with Sonara.
Submit 10x as many applications with less effort than one manual application.
FAQs About Help Desk Support Lead Jobs at Skyward IT Solutions, LLC
What is the work location for this position at Skyward IT Solutions, LLC?
This job at Skyward IT Solutions, LLC is located in Rockville, MD, according to the details provided by the employer. Some roles may also include multiple work locations depending on the requirement.
What pay range can candidates expect for this role at Skyward IT Solutions, LLC?
Employer has not shared pay details for this role.
What employment applies to this position at Skyward IT Solutions, LLC?
Skyward IT Solutions, LLC lists this position under the following employment categories:
- Flexible-schedule
- Full-time
What experience level is required for this role at Skyward IT Solutions, LLC?
Skyward IT Solutions, LLC is looking for a candidate with "Director" experience level.
What benefits are offered by Skyward IT Solutions, LLC for this role?
Skyward IT Solutions, LLC offers following benefits: Health Insurance, Dental Insurance, Vision Insurance, Disability Insurance, Life Insurance, Paid Holidays, Paid Vacation, Paid Sick Leave, Parental and Family Leave, Career Development, 401k Matching/Retirement Savings, and Tuition/Education Assistance for this position. Actual benefits may vary depending on the employer's policies and employment terms.
What is the process to apply for this position at Skyward IT Solutions, LLC?
You can apply for this role at Skyward IT Solutions, LLC either through Sonara's automated application system, which helps you submit applications 10X faster with minimal effort, or by applying manually using the direct link on the job page.