Windows Digital Services Technical Lead

Job ID: 113251
Location: Home, DC  [Remote]
Category: App/Dev
Employment Type: Contract
Date Added: 10/13/2026
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Role Summary

This technical leadership position leads Windows digital services initiatives within enterprise and cloud environments. The role supports modernization, automation, and DevSecOps practices while coordinating cross-functional teams to deliver reliable, secure, and scalable Windows and cloud infrastructure solutions.

Responsibilities

  • Configure, administer, and maintain Windows Server and enterprise Windows environments.
  • Monitor system performance, troubleshoot technical issues, and perform root-cause analysis for Windows-based services.
  • Apply patches, updates, and security configurations in accordance with established policies and standards, including DISA STIG and CIS benchmarks.
  • Administer Windows Public Key Infrastructure, including certificate issuance, renewal, maintenance, and troubleshooting.
  • Support Windows services such as Internet Information Services (IIS), as well as backup, recovery, and storage solutions.
  • Lead technical initiatives focused on modernization, continuous delivery, infrastructure automation, and operational improvement.
  • Collaborate with cloud reliability engineers, developers, security teams, and other stakeholders to deliver secure and reliable solutions.
  • Use observability platforms such as Datadog and CloudWatch for monitoring, diagnostics, alerting, and incident response.
  • Develop and maintain operational documentation, incident reports, technical procedures, and process standards.
  • Support Agile planning and delivery activities, establish standard procedures, and identify opportunities to improve team efficiency.

Qualifications

  • 12+ years of experience administering Active Directory, Group Policy, DNS, DHCP, Windows Server, and related enterprise services.
  • Advanced experience with scripting and automation using technologies such as PowerShell, Python, Bash, or Java.
  • Strong experience with AWS services, including EC2, EKS, CloudWatch, and cloud security technologies.
  • Hands-on experience with Kubernetes, AWS EKS, GitLab CI/CD, and observability platforms such as Datadog.
  • Strong knowledge of DevSecOps, application development, cloud security, and Infrastructure as Code using Terraform.
  • Experience leading technical teams, coordinating complex initiatives, and managing critical incidents.
  • Strong troubleshooting, incident management, technical documentation, and communication skills.
  • Ability to balance strategic planning with hands-on technical execution and manage multiple priorities.
  • AWS Certified Solutions Architect Professional and AWS Certified Security – Specialty certifications are preferred.
  • U.S. citizenship is required due to eligibility requirements for a U.S. Government security clearance.

Publishing Pay Range: $90.00 – $95.00 hourly
This is a fully remote role and can be performed from an approved location.

About GDH:
At GDH, we believe in the power of people and the importance of caring. Our culture statement, “We care about people,” isn’t just a tagline – it’s the core of everything we do. GDH is a premier staffing and talent solutions company dedicated to helping businesses find the best talent and assisting job seekers in finding their dream jobs.

Who We Are:
GDH, founded in 2001, has grown into a leader in providing staffing solutions across various industries. We specialize in IT across several sectors, connecting top talent with leading enterprises. As a Best of Staffing firm recognized for excellence in client, employee, talent, and women’s services, we pride ourselves on our commitment to quality and service.

GDH Benefits

GDH offers a range of employee benefits that are designed to promote well-being and help maintain a healthy work-life balance. These comprehensive benefits cover various aspects of an employee’s life and aim to enhance their overall experience with the company. Our health benefits include three medical insurance options with access to KISx Card, Zero Card, and HealthJoy concierge services. Other plan offerings include dental, vision, life, disability, supplemental insurance, and pet insurance plans. Enjoy additional perks like holiday pay, 401(k) plan, direct deposit, an employee referral program, work-life balance benefits, a Wellbeats membership, a discounted gym membership program, and more!  For more detailed information on benefits, please go to GDH’s website under the tab for candidates.

GDH provides equal employment opportunities (EEO) to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, gender, sex (including pregnancy), sexual orientation, gender identity, national origin, age, disability, genetic information, marital status, ancestry, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable federal, state, and local laws. Applicants with disabilities who require an accommodation or assistance in applying and/or for interviewing, please contact our HR Department.

Please visit our notice of collection for California applicants.

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