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 clear reproduction steps and context
• Own technical onboarding for each new pilot from kickoff to go-live
• Work with customer enterprise IT teams to configure SSO and identity provider access, including Okta and other IdPs
• Ensure pilot users belong to groups authorized to access the platform
• Handle desktop app rollout on Mac and Windows, including installation, OS permissions, and compatibility with customer MDM and VPN setups
• Own CRM connection and onboarding with customer CRM administrators
• Ensure users have the correct CRM permissions
• Lead onboarding meetings with customer IT teams and train them on the platform
• Troubleshoot onboarding blockers and escalate to the CTO when needed
• Drive follow-ups with customer stakeholders 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, including desktop app installations and OS-level permissions
• Experience with CRM administration or integrations, such as Salesforce or HubSpot, especially user permissions
• Structured debugging approach able to distinguish user error from real bugs and support conclusions with evidence
• Ownership of deadlines and follow-ups across multiple customers
• Experience in a technical support, support engineering, IT, or implementation role
• Experience in a B2B SaaS company selling to enterprises is ideally preferred
• Experience with Google Workspace or Microsoft 365 administration, especially calendar app approvals, is nice to have
• Familiarity with enterprise security and IT review processes is nice to have
• Basic scripting or log analysis skills for debugging are nice to have
• Startup experience is nice to have

• Security through careful client vetting to minimize risks and ensure reliability and timely payments
• Career support and assistance finding new opportunities if a project is not the right fit
• 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