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
- Predictive Index assessment
- Recruiter / hiring manager screen
- Technic