Technical Support Engineer

Technical Support Engineer

Our client is an AI sales coach that provides sales reps with real-time guidance during live calls, pre-call dossiers, and automatic CRM sync. Selling to enterprise sales teams in the US and scaling pilots across a growing list of accounts, Othello connects directly with customer IT teams, CRM admins, and end users. What You’ll Do The Technical Support Engineer serves as the technical front line between customers and the R&D team. You will own two key areas: resolving customer technical issues before they reach engineering and getting every new pilot technically live on schedule. This position combines direct technical support and triage with technical onboarding responsibilities. You will work directly with customer IT teams, CRM admins, and end users across the US, managing issues end to end, unblocking adoption barriers, and escalating complex matters to the CTO when necessary. Key Responsibilities Technical Support and Triage • Own incoming technical issues end to end, from first report to resolution. • Resolve issues directly with the customer or debug them using internal tools, acting as a filter before R&D to classify whether an issue is user error, a product knowledge gap, or a real bug. • Coach users through product gaps to prevent recurring questions. • Confirm bugs with certainty and report them to R&D with clear reproduction steps and context. Technical Onboarding • Own the technical onboarding of each new pilot, from kickoff to go-live, hitting committed onboarding deadlines. • Work with enterprise IT to set up SSO and identity provider access (Okta and other IdPs), ensuring pilot users are properly grouped and assigned. • Secure approvals for calendar integrations (Google Calendar or Outlook) and manage CRM connections with customer CRM admins. • Handle desktop app rollouts on Mac and Windows, including installation, OS permissions, and compatibility with customer MDM and VPN setups. • Lead onboarding meetings with customer IT teams, train them on the platform, and troubleshoot any blockers. Required Experience and Technical Skills • 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. Core Competencies • Strong customer-facing communication skills with the ability to explain technical concepts plainly to non-technical users as well as 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. Nice to Have • Experience with Google Workspace or Microsoft 365 admin, especially calendar app approvals and OAuth/admin-consent issues. • Familiarity with enterprise security, IT review processes, and domain allowlisting. • Basic scripting or log analysis skills for debugging. • Prior startup experience.