Technical Support Engineer - CiraSync On-Premise

About the role

CiraSync On-Premise is our self-hosted contact and calendar synchronization platform for Microsoft Exchange environments. It is the most technically demanding product in our portfolio, and today only a small number of agents can support it. We are hiring a dedicated engineer to expand that coverage.

You will work directly inside customer environments — on-premises Exchange, Active Directory, Windows Server, and the networking layer around them — diagnosing sync, permission, mail flow, and connectivity issues alongside enterprise IT teams. This is a support role that suits a working IT administrator: most of the day is spent doing the kind of troubleshooting a sysadmin already does, but across many customer environments instead of one.

What you will do

• Own on-premises support tickets end to end, from intake through resolution and follow-up
• Work with customers over email, phone, Zoom, and Microsoft Teams, including live screen-share troubleshooting sessions
• Analyze application logs, Windows event logs, Exchange logs, and PowerShell output to isolate root cause
• Reproduce customer issues in an internal lab environment before escalating
• Escalate to engineering with clear, structured reproduction steps and evidence
• Support customer upgrades, server migrations, and environment health checks
• Write and maintain knowledge base articles so that on-premises expertise is documented rather than held individually
• Participate in internal knowledge sharing to reduce single-point coverage risk on this product

What you’ll bring

• 3+ years as an IT Administrator or Systems Administrator in a Windows Server environment
• Hands-on on-premises Exchange Server administration (2013 / 2016 / 2019 / SE): mailbox and public folder management, permissions, mail flow, Exchange Management Shell
• Hands-on on-premises Active Directory: organizational units, security and distribution groups, delegated permissions, user attributes, Group Policy
• On-premises networking troubleshooting: DNS, firewalls and proxies, TLS certificates, ports and service accounts, connectivity testing
• Windows Server administration, including services, IIS basics, and log file analysis
• Comfortable working in PowerShell
• Fluent spoken and written English, with the confidence to lead a call with an enterprise IT administrator
• Able to explain technical findings clearly to both hands-on admins and non-technical stakeholders

Nice to have

• Exchange Online and Microsoft 365 administration
• Entra ID (Azure AD), hybrid Exchange, Entra Connect / Azure AD Connect
• SQL Server fundamentals
• Prior B2B technical support experience with a ticketing system (Salesforce, Zendesk, or similar)
• Experience writing customer-facing documentation or knowledge base content
• Relevant Microsoft certifications

Working arrangement and home office requirements

• Fully remote, work from home
• 8-hour workday, Monday through Friday, aligned to US business hours across US time zones; your exact shift will be set after the training period
• A quiet, dedicated work area suitable for customer calls and video meetings
• Reliable high-speed internet connection (wired preferred; recommended minimum 50 Mbps down / 10 Mbps up)
• Quality headset and webcam for customer-facing calls
• Structured onboarding and training on CiraSync On-Premises before shift assignment and independent ticket ownership

Conditions of employment

• Exclusive engagement. Secondary employment or contract work ("moonlighting") is not permitted.
• Endpoint protection. Company-managed endpoint protection software must be installed and remain active on the computer used for work.
• Background screening. A personal background check is required prior to start.
• Assessments. Candidates complete a Predictive Index behavioral and cognitive assessment and a live technical screening.

Hiring process

1. Predictive Index assessment
2. Recruiter / hiring manager screen
3. Technical screening — scenario-based, covering Exchange on-premises, Active Directory, and network troubleshooting
4. Interview with the support leadership team
5. Background screening
6. Offer

Cira Apps is committed to a diverse and inclusive workplace. Cira Apps is an equal opportunity employer and does not discriminate based on race, national origin, gender, gender identity, sexual orientation, disability, age, or other legally protected status. If you would like to request an accommodation, please notify us at [email protected]