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Remote, Oregon, United States
Remote only
Technical Support Engineer
Location: Remote (United States)
Target Start Date: April 2026
About CyberNut
CyberNut is a security awareness training platform built specifically for K-12 schools. Our platform helps teachers, staff, and students recognize and report suspicious emails before they become real security incidents. We partner with school districts across the country to deploy phishing simulations, reporting tools, and security awareness programs designed for education environments.
Position Overview
The Technical Support Engineer will serve as the front-line owner of customer support tickets, independently diagnosing and resolving technical issues for school IT administrators across the CyberNut platform.
In this role, you will triage incoming tickets, troubleshoot email delivery and reporting issues, resolve browser extension and add-on errors, guide customers through onboarding and campaign configuration, and escalate confirmed bugs to engineering with thorough documentation. You will be the primary ticket handler for all incoming issues, independently resolving the majority of tickets without escalation—freeing the rest of the support team to focus on complex platform investigations and engineering coordination.
Key Responsibilities
Own Tier 1 support across all incoming channels (email, web form, chat) with a target first response time under 2 hours.
Diagnose and resolve email delivery issues, including phishing simulations not sending, emails stuck in pending, and campaign scheduling problems.
Resolve browser extension and add-on issues for the Chrome extension, Gmail add-on, and Outlook add-in, including installation errors, missing icons, and update problems.
Guide customers through onboarding, training campaign setup, team configuration, and platform walkthroughs.
Troubleshoot SSO and authentication issues, including SAML configuration, expired certificates, and login failures across Google and Microsoft identity providers.
Investigate user sync and directory integration issues with Google Workspace and Microsoft 365.
Escalate confirmed bugs to engineering with clear reproduction steps, relevant logs, and customer context via our internal ticketing process (Linear).
Verify fixes with customers after engineering deployments and close tickets.
Contribute to an internal knowledge base by documenting resolution steps for recurring issues.
Partner with Customer Success, Engineering, and Product teams to resolve issues and surface patterns that inform product improvements.
Required Technical Skills
Strong understanding of email systems (SMTP, SPF, DKIM, DMARC, email headers)—critical for reported threats triage and email delivery issues, which represent over 20% of support tickets.
Experience with browser extensions and web technologies—for add-on/extension troubleshooting (Chrome, Outlook).
SSO/SAML/OAuth configuration experience—for authentication issues.
Google Workspace and Microsoft 365 admin console familiarity—for directory sync, user management, and integration troubleshooting.
Basic API and log reading skills to interpret error messages, API responses, and webhook events without needing infrastructure access.
Familiarity with reading AWS CloudWatch logs to investigate issues before escalating.
SQL basics for read-only queries to verify data discrepancies without engineering involvement.
Required Non-Technical Skills
Excellent written communication— Clear, empathetic responses are critical for customer retention.
Triage instinct—ability to quickly classify tickets and determine if engineering is genuinely needed.
Customer-facing confidence—able to conduct screen-share troubleshooting calls when needed.
Documentation mindset—willing to build knowledge base articles as ticket patterns emerge. This is an investment in future scalability.
Education
Bachelor’s degree in Computer Science, Information Technology, or a related field, or equivalent experience.
Nice to Have
Previous experience in a SaaS support or customer-facing IT role.
Experience working in, or with K-12 school districts is highly desirable.
Familiarity with HubSpot Help Desk or similar ticketing platforms.
Exposure to cybersecurity concepts: phishing, social engineering, threat reporting workflows.
Experience with Linear, Jira, or similar engineering project management tools.
Scripting basics (Python, Bash, or JavaScript).
Skills & Tools Used
Strong troubleshooting and problem-solving ability.
Ability to guide school IT staff through technical troubleshooting steps.
Clear written and verbal communication skills.
Google Workspace Admin Console, Microsoft 365 Admin Center, AWS Console (read-only), HubSpot, Slack, Linear, CyberNut Admin Portal, Fathom, Zoom.
Travel: Limited travel, with likely attending one company offsite, and 1-2 conferences annually. Benefits: Includes access to the company’s group health, dental, and vision insurance plans, basic life insurance, 18 days PTO, and 8 paid holidays.
