System Administrator

At Dollar Days, our mission is simple:
Make a difference for those who are making a difference.

Since 2001, Dollar Days has partnered with nonprofits, schools, churches, healthcare organizations, disaster relief agencies, and other mission-driven organizations by providing wholesale products that help communities across the country. Every day, our team supports organizations making a positive impact, and we're looking for someone who wants their work to make a difference too.

About the Role

Dollar Days is looking for a Systems Administrator with a strong technical foundation who enjoys helping people and wants to continue growing their IT career. This is a hands‑on role supporting approximately 50 employees and serving as a key technology resource for the organization.

You may have 2-5 years of experience in systems administration, IT infrastructure, or desktop support with increasing responsibility. Success in this role is about more than technical ability. We're looking for someone who takes ownership, communicates well, solves problems, and provides exceptional customer service.

The right person will be curious, motivated, eager to learn, and interested in building a long‑term career with a mission‑driven company. Technical skills can continue to develop, but a positive attitude, strong work ethic, and genuine desire to support others are essential.

What You’ll Do

As our Systems Administrator, you'll be responsible for maintaining a secure, reliable, and efficient technology environment while providing exceptional support to our employees.

Responsibilities include:

• Administer Microsoft 365, Azure Hybrid Active Directory, and Windows infrastructure.
• Manage Azure cloud resources and support ongoing cloud initiatives.
• Support AWS environments as needed.
• Deploy, configure, and maintain Windows laptops and Mac computers.
• Manage Windows and Linux servers.
• Provide day‑to‑day technical support for employees, including hardware, printers, software, and general troubleshooting.
• Administer firewalls, networking, endpoint detection and response (EDR), multifactor authentication (MFA), and cybersecurity tools.
• Support and maintain our hosted SaaS phone system.
• Assist with cybersecurity awareness, best practices, and continuous security improvements.
• Help establish governance and best practices around Artificial Intelligence usage within the organization.
• Identify opportunities to improve processes, security, automation, and overall technology efficiency.
• Partner with leadership on future technology initiatives while ensuring our systems remain reliable and secure.

Required Qualifications

• 2+ years of experience in Systems Administration, IT Support, Infrastructure, or a similar technical role.
• Experience supporting Microsoft 365 and Windows environments.
• Working knowledge of Azure Active Directory (Entra ) or Hybrid Active Directory.
• Experience deploying and supporting Windows laptops and hardware.
• Basic networking and infrastructure troubleshooting experience.
• Strong customer service and communication skills.
• Excellent problem‑solving skills with the ability to prioritize multiple requests.
• Highly organized with strong attention to detail.
• Ability to work onsite Monday through Friday.

Preferred Qualifications

• AWS experience.
• Cybersecurity experience, including EDR, MFA, or endpoint security.
• Experience administering SaaS applications.
• Interest or experience in AI governance or AI security.
• Bachelor's degree in Computer Science, Information Technology, or a related field (or equivalent experience).

Who You Are

The ideal candidate is someone people enjoy calling when they need IT help because you genuinely like helping others. You take pride in providing outstanding customer service, enjoy figuring things out, and don't wait to be asked before jumping in to solve a problem. You understand that great IT isn't just about technology. It's about supporting the people who rely on it every day.

You're someone who:

• Takes ownership and follows through.
• Has a positive attitude and enjoys supporting others.
• Builds trust through excellent communication.
• Thrives in a fast‑paced, evolving environment.
• Is dependable, organized, and detail‑oriented.
• Is…