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