Product Support Specialist

Role overview Provide frontline technical support to business customers using a broad retail software platform, resolving issues that can affect active store operations. You’ll investigate problems across software, payments, hardware, inventory, and integrations, communicate clearly under pressure, and document or escalate cases so customers and support colleagues can act on the next steps.

Responsibilities - Handle customer requests by email, phone, and live chat across point-of-sale, online ordering, payments, loyalty, hardware, and integrations. - Troubleshoot configuration and transaction issues, receipt reconciliation, menu synchronization, discounts, and pricing. - Help set up and diagnose registers, printers, scanners, cash drawers, scales, and computers. - Triage payment problems such as account linking, funding delays, authorization errors, returns, and suspected fraud. - Assist with inventory, catalog, labeling, pricing, and basic regulatory workflow questions; route compliance-adjacent issues with complete context. - Validate integration setups, investigate synchronization failures, and process API-key requests. - Use AI-assisted support tools, record each contact and its outcome, and escalate cases when progress stalls or specialist help is needed.

Requirements - At least two years in a customer-facing support role, preferably supporting a software-as-a-service product. - Strong written and spoken communication, including the ability to explain technical issues in plain language. - Comfort troubleshooting several product areas and using web-based software, customer-management tools, and Google Workspace. - Thorough documentation habits so case notes clearly capture the issue, steps taken, outcome, and next actions. - Composure with frustrated customers and urgent issues, plus sound judgment about when and how to escalate. - Curiosity about AI support tools and willingness to learn and report gaps as the tools evolve. - Flexibility for evening, weekend, and holiday shifts in a seven-day operation running from 5 a.m. to 9 p.m. Pacific Time.

Nice to have Experience with point-of-sale systems, retail operations technology, cannabis compliance, or dispensary operations is useful. Familiarity with ticketing, customer-management, messaging, or video-call tools is also a plus.

Benefits and work setup This is a full-time remote position with schedules assigned through a vacation-bid process. Listed benefits include medical, dental, and vision coverage, stock options, a technology allowance, and flexible vacation and sick time.