Technical Support Engineer

• Serve as the technical front line between customers and the R&D team
• Own incoming technical issues end to end, from first report to resolution
• Resolve customer issues directly or debug them using internal tools before escalating to R&D
• Classify issues as user error, product knowledge gaps, or real bugs
• Coach users through product gaps to prevent recurring questions
• Confirm bugs and report them to R&D with reproduction steps and context
• Own technical onboarding of each new pilot from kickoff to go-live
• Set up SSO and identity provider access with enterprise IT, including Okta and other IdPs
• Secure approvals for Google Calendar or Outlook integrations
• Manage CRM connections with customer CRM administrators
• Handle Mac and Windows desktop app rollouts, OS permissions, MDM, and VPN compatibility
• Lead onboarding meetings, train customer IT teams, and troubleshoot blockers
• Manage issues for customer IT teams, CRM admins, and end users across the US, escalating complex matters to the CTO when necessary

• Native or near-native English, comfortable leading calls with US customers ranging from end users to enterprise IT
• Experience in a technical support, support engineering, IT, or implementation role, ideally at a B2B SaaS company selling to enterprises
• Hands-on IT experience with SSO and identity providers (Okta, Microsoft Entra ID or similar), user/group management, MDM, and VPNs
• Strong Mac and Windows troubleshooting skills, including desktop app installs, OS-level permissions (mic, screen recording, accessibility), and MDM deployment
• Experience with CRM administration or integrations (e.g., Salesforce, HubSpot), particularly regarding user permissions and connected apps
• A structured debugging approach to separate user error from real bugs using logs, reproduction steps, and clear evidence
• Proven ownership of deadlines and follow-ups across multiple concurrent customer accounts
• Strong customer-facing communication skills with the ability to explain technical concepts plainly to non-technical users and speak to enterprise IT admins as peers
• Methodical and structured approach to debugging and problem-solving
• Proactive ownership and accountability over onboarding deadlines and issue resolution
• Ability to manage and prioritize multiple customer implementations simultaneously
• Experience with Google Workspace or Microsoft 365 admin, especially calendar app approvals and OAuth/admin-consent issues (nice to have)
• Familiarity with enterprise security, IT review processes, and domain allowlisting (nice to have)
• Basic scripting or log analysis skills for debugging (nice to have)
• Prior startup experience (nice to have)