Help Desk Support Lead

atSkywardRemoteUS flagMarylandFull-timeIT SupportSenior$78k – $95k/year

Posted Sep 11

This is a fully remote position, open to applicants in Maryland.

📋 Description

• Serve as the primary support for CMS's enterprise AI services, ensuring that high-profile users remain productive and satisfied.

• Manage the support queue, establish benchmarks for response times and quality, and maintain the team's workflow efficiently.

• Deliver exceptional support to CMS stakeholders, including the Administrator's office, with professionalism and discretion.

• Guide and mentor support personnel, develop playbooks, and elevate the overall performance of the team.

• Relay feedback from leadership to the product, AI, and engineering teams.

• Keep standard operating procedures (SOPs) and knowledge base articles updated.

• Assist with user acceptance testing (UAT) and conduct post-deployment smoke testing.


⛳️ Requirements

• A bachelor’s degree and over 5 years of experience in IT support, including team-lead or supervisory roles.

• Outstanding communication and interpersonal skills, with the ability to support senior executives with professionalism.

• A composed and resilient attitude in high-pressure, high-visibility scenarios.

• Proficient in researching and resolving technically complex challenges.

• Capability to obtain and maintain a Public Trust security clearance.

• Employment offers are contingent upon satisfactory results of a background check.

• Experience in supporting AI/ML, chatbot, or LLM-based tools is preferred.

• Experience in providing executive or VIP-level support is preferred.

• Previous experience supporting CMS or another federal agency is preferred.


🏝️ Benefits

• Medical, dental, and vision insurance.

• 15 days of paid leave.

• 7 days of sick leave.

• 2 days of bereavement leave.

• 11 paid Federal holidays.

• Up to 40 hours for jury duty.

• 401K plan with a 4% employer contribution and no vesting period.

• Up to 4 weeks of paid paternity and maternity leave.

• Company-provided laptop.

• $5,000 per year allocated for professional development.

• $600 per year for technical supplies and equipment.

• $2,000 referral bonus.

• Life and disability insurance.

• Health Savings Account (HSA) and Flexible Spending Account (FSA).

• Voluntary benefits including Legal Shield and ID Shield.

• Flexible working hours.

• Remote work opportunities.

• Chance to collaborate with a motivated team focused on modernizing government services through innovative technology and solutions.

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