Endpoint Engineer

We are seeking a Senior Endpoint Systems Engineer to serve as the final escalation point for all Windows and POS related endpoint environments across a large scale restaurant/retail footprint. This role owns the design, certification, and ongoing support of Windows 10 and Windows 11 images, drives endpoint and POS strategy across both cloud and on prem environments, and builds automation using PowerShell (primary) and Python. The engineer will provide Level 3 POS support for Windows based POS systems, including hands on support of terminals, printers, pin pads, and kitchen display systems, and will manage endpoint tooling (e.g., Avanti) to ensure performance, compliance, and scalability across thousands of endpoints. Responsibilities include root cause analysis for escalated issues, PCI vulnerability remediation and patching, monthly compliance scanning, architecture and change documentation, and clear communication with leadership and security teams. The ideal candidate has deep POS experience in restaurant or retail environments, strong networking fundamentals, ITIL foundation knowledge, proven automation expertise, and experience influencing endpoint strategy, with certifications such as Microsoft 365 Modern Desktop Administrator, ITIL v4, Azure Fundamentals, or equivalent. This is a hands on, advanced engineering role-not desktop support-requiring expertise in endpoint design, compliance, and automation at scale.

Compensation:
$43/hr to $45/hr.
Exact compensation may vary based on several factors, including skills, experience, and education.
Employees in this role will enjoy a comprehensive benefits package starting on day one of
employment, including options for medical, dental, and vision insurance. Eligibility to enroll in
the 401(k) retirement plan begins after 90 days of employment. Additionally, employees in this
role will have access to paid sick leave and other paid time off benefits as required under the
applicable law of the worksite location.

We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment regardless of their race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or recruiting process, please send a request to View email address on click.appcast.io learn more about how we collect, keep, and process your private information, please review Insight Global's Workforce Privacy Policy:


Required Skills & Experience
- 7+ years of experience
- PowerShell or Python scripting experience
- POS experience
o Within a windows or Linux based environment
- Endpoint management experience both on Prem and cloud
- Experience automating processes
- Experience driving end point and POS strategy influence
- Some sort of certifications - Microsoft 365 Certified: Modern Desktop Administrator Associate (MD-100, MD-101), ITILv4, Azure Fundamentals Agile Certification Microsoft MCSA / MCP or equivalent


Nice to Have Skills & Experience
- PAR POS experience
- AI - how to leverage it for automation


Benefit packages for this role will start on the 1st day of employment and include medical, dental, and vision insurance, as well as HSA, FSA, and DCFSA account options, and 401k retirement account access with employer matching. Employees in this role are also entitled to paid sick leave and/or other paid time off as provided by applicable law.