Technical Support Engineer

• Own incoming technical issues end to end, from first report to resolution
• Resolve customer issues directly or debug them using internal tools
• Filter issues before R&D by determining whether they are user errors, 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 for each new pilot from kickoff to go-live
• Configure SSO and identity provider access with customer enterprise IT teams
• Ensure pilot users belong to groups authorized for access
• Manage desktop app rollout on Mac and Windows, including installation, OS permissions, MDM, VPN, and compatibility
• Own CRM connection and onboarding with customer CRM administrators
• Lead onboarding meetings with customer IT teams and train them on the platform
• Troubleshoot onboarding blockers and escalate to the CTO when needed
• Drive stakeholder follow-ups and meet committed onboarding deadlines

• Native or near-native English
• Comfortable leading calls with US customers, from end users to enterprise IT
• Hands-on IT experience with SSO and identity providers such as Okta or Microsoft Entra ID
• Experience with MDM, VPNs, and user and group management
• Strong Mac and Windows troubleshooting skills
• Experience installing desktop applications and managing OS-level permissions
• Experience with CRM administration or integrations, such as Salesforce or HubSpot, especially user permissions
• Structured debugging approach to distinguish user error from real bugs and support conclusions with evidence
• Ability to own deadlines and follow-ups across multiple customers
• Experience in a technical support, support engineering, IT, or implementation role
• B2B SaaS experience selling to enterprises is ideal
• Experience with Google Workspace or Microsoft 365 administration, especially calendar app approvals, is a plus
• Familiarity with enterprise security and IT review processes is a plus
• Basic scripting or log analysis skills for debugging is a plus
• Startup experience is a plus

• Security through careful client vetting to minimize risks and ensure reliable, timely payments
• Career support and help finding new project opportunities
• Legal assistance with independent contractor or sole proprietorship status, taxes, and related processes
• English courses
• Professional growth opportunities
• Team-building events
• People-first management with minimal bureaucracy
• Friendly company culture
• Flexible working hours
• 29 days of PTO (18 working days per year plus all national holidays)
• 10 paid recovery days
• Full financial and legal support for independent contractors
• Free English classes with native speakers or Ukrainian teachers
• Dedicated HR support