Technical Support Representative

Role overview Resolve technical issues for customers using a retail point-of-sale platform, with most support delivered through live chat. This Tier 2 role handles cases that need more investigation than initial automated support can provide, spanning software, POS equipment, and connected devices. You’ll own cases through resolution or escalation and share recurring issues with teams working on the product and customer experience.

Responsibilities - Respond to escalated customer issues, primarily through live chat, and provide timely, clear guidance. - Troubleshoot POS software and retail hardware such as receipt printers and other connected devices. - Gather relevant details, investigate symptoms, and identify likely causes before recommending next steps. - Document customer interactions, troubleshooting, and resolutions; follow up and escalate when needed. - Work with advanced support, product, quality, and development teams on complex cases. - Report recurring problems and customer feedback to help improve support processes and documentation.

Requirements - At least two years in customer-facing support, technical support, customer service, or retail operations. - Experience troubleshooting POS systems and related hardware, remotely or in person. - Ability to investigate software, hardware, or other complex technical problems methodically. - Excellent written English for explaining technical information clearly in chat, plus strong spoken English. - Patience, attention to detail, accountability, and a calm approach to urgent or frustrating cases. - Comfort with web software, support platforms, CRM systems, and AI-assisted tools; ability to work independently and escalate effectively. - Availability for the required weekend schedule and Pacific Time coverage.

Nice to have - Experience with SaaS products, retail operations, inventory systems, or e-commerce. - Familiarity with APIs, integrations, application logs, support tools, or cannabis retail compliance systems. - Relevant IT education or technical certifications.

Benefits and work setup - Full-time, remote B2B contract paid in USD, with hours tracked through a timekeeping tool. - After roughly two months of weekday training, the regular schedule is Saturday through Wednesday, with an assigned eight-hour shift between 6 a.m. and 6 p.m. Pacific Time and a one-hour unpaid lunch. - Includes 20 paid days off, three paid sick days, medical insurance after an introductory period, and equipment reimbursement.