System Engineer

Penta Software is transforming how construction companies leverage technology on job sites. With over 50 years of expertise, our ERP platform helps large specialty contractors streamline operations and improve profitability. We're growing fast—and we want you to be part of it.

This System Engineer role is an early-career position on our IT team, keeping our customers' ERP systems accessible, secure, and cost-effective, and keeping Penta's internal infrastructure available so we can deliver quality products and services. You'll work under senior engineers and architects, with clearly scoped tasks, hands-on mentorship, and a defined path toward more advanced work.

This job is for you if:

• You have foundational familiarity with Windows Server and networking fundamentals, plus some exposure to cloud infrastructure (AWS preferred).
• You have a genuine desire to learn Active Directory, SAML, AWS (EC2, Workspaces, and other services), Linux, Oracle, and monitoring tools like Zabbix.
• You dive deep to understand root cause, and you're comfortable escalating when the cause isn't yet clear.
• You bring a systematic approach to problem-solving and learn quickly from both successes and failures.
• You thrive in a fast-paced environment and are responsive to customer needs.
• You enjoy autonomy but welcome structure and feedback as you grow, and you proactively seek out coaching on your career development.
• You work well collaboratively in a fully remote, transparent environment.

Here's what an ordinary week might look like:

• Respond to customer inquiries and help troubleshoot and resolve issues, handling first- and second-line support for things like network interruptions and software installation/configuration.
• Execute well-defined tasks within established runbooks, partnering with senior engineers to build your troubleshooting instincts and escalating when you hit an unknown.
• Install, configure, test, and maintain operating systems, application software, and system management tools under guidance, including hosted Windows and Linux servers in AWS.
• Perform routine system health checks (logs, disk space, processor/memory utilization) and assist with patching, backups, and anti-threat measures.
• Maintain basic PowerShell scripts to reduce manual effort, and assist with Microsoft 365 administration tasks.
• Occasionally provide on-call coverage or work outside standard hours as your skills develop.

Here's the experience we expect will help you excel in this role:

1–2 years in a technical support, help desk, or systems administration role, with exposure to several of the following:

• Basic administration of Windows-based environments (Linux exposure a plus)
• Networking fundamentals (TCP/IP, DNS, DHCP, VPN concepts)
• Some exposure to cloud technologies, preferably AWS
• Basic scripting ability, or a strong willingness to learn (PowerShell preferred)
• Core cybersecurity hygiene and best practices
• Clear written and verbal client communication
• A strong desire to learn and receptiveness to mentorship

Even more helpful:

• CompTIA A+ or Network+ certification
• AWS Certified Cloud Practitioner (or Solutions Architect – Associate)
• Microsoft certifications (e.g., MS-900, AZ-900, or Windows Server)
• Exposure to Oracle administration
• Hands-on exposure to monitoring (Zabbix), RMM (Datto), or automation

Here's what Penta offers:

• An Agile organization working in a fast-paced, ever-changing, exciting environment.
• Work with mentors who care about your personal growth and development.
• A culture committed to continued growth and development.
• An onboarding experience designed to set you up for success by providing the support you need with clearly understood expectations.
• A team with rich construction payroll domain knowledge to help you understand our users and the challenges they face.
• A 100% remote work environment.
• Comprehensive benefits including Health, Dental, Vision, Disability, Life Insurance, Paid Maternity and Paternity Leave, and 401k with company match.

Penta cannot provide Visa sponsorship at this time.