Our client is building AI-powered Copilots and workflow automation for modern accounting firms! Our client is a post-product-market-fit B2B SaaS startup with rapidly growing ARR and customer usage. Our platform helps tax firms automate data intake and service delivery, and we’re scaling fast.

We’re looking for an experienced Windows System Administrator, with a deep understanding and experience supporting RDP, to support our customers in hosted Windows environments. You’ll troubleshoot RDP access issues, printing problems, profile inconsistencies, and hosted application errors and help tax professionals stay productive during their busiest season.

NOTE: This is a contract to hire role. Our client intends have this person work as a contractor until April, then could potentially convert this to a full-time position.

What You'll Own And Drive

Customer-Facing Tech Support: Diagnose and resolve customer issues related to

Remote Desktop (RDP) access, including login failures, session lag, and connection

drops in hosted Windows environments.

Hosted Application Support: Support users running tax software like QuickBooks,

Lacerte, and Drake within virtual desktop or RDP environments. Troubleshoot

performance and compatibility issues.

User and Access Management: Manage user accounts, reset passwords, resolve

profile corruption and assist with MFA setup or account lockouts.

Peripheral Troubleshooting: Assist with printing, drive mapping, and shared folder

issues common to remote desktop environments.

Backup Oversight: Monitor and verify system and user data backups for hosted

environments. Identify and escalate backup failures, and assist in the execution of

restore operations when needed. Contribute to improving backup workflows and

reliability.

Escalation Handling: Independently triage and resolve Tier 1–2 issues, and escalate system-wide or complex problems to the engineering team with clear documentation and logs.

Documentation and FAQs: Contribute to internal and customer-facing documentation by capturing fixes, recurring issues, and process improvements.

What We’re Looking For

Hands-on experience with Active Directory, Group Policy management, and Windows Firewall.

Experience managing EC2-based Windows servers, ideally with AWS SSM.

Track record of customer-facing support for Windows Server and RDP environments, including helpdesk issue triage and resolution.

Strong knowledge of user profile management and administration in multi-user Windows environments.

Experience configuring and maintaining hosted desktop platforms (Amazon

WorkSpaces, Windows Server with RDP, or Citrix): user provisioning, patching, network access, and image management.

Proficiency troubleshooting networking, DNS, VPN, zero trust connectivity, and printing issues in both local and remote Windows environments.

Excellent English communication skills, with a clear and empathetic approach (written and verbal).

Proven ability to work independently, take initiative, and proactively resolve issues.

Bonus Skills

Experience supporting US-based accounting or tax firms

Familiarity with popular accounting and tax software such as QuickBooks and Lacerte.

Proficiency in Python programming language.

Strong scripting and automation skills to improve workflows.

Knowledge of cloud-hosted Windows environments like AWS WorkSpaces and Microsoft Azure.

Understanding of compliance frameworks including SOC 2 and IRS Publication 1075.

We are a small team that moves quickly. If you thrive in customer-facing environments, have deep expertise in Windows hosting, and enjoy working independently, we’d love to meet you.

** Please note: We cannot currently provide visa sponsorship. If you require visa sponsorship now, or in the future, please do not apply for this position. **

Windows System Administrator

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