Technical Support Representative - Sweed

About Sweed

We're Sweed, a product-driven startup building an all-in-one cannabis retail platform. Our enterprise-grade platform combines POS, eCommerce, Marketing, Analytics, and Inventory Management into a single, seamless solution.

We're looking for a Technical Support Representative (Tier 2) to join our growing Customer Support team and help our customers resolve technical challenges, keep their businesses running smoothly, and get the most out of Sweed.

About the Role

As a Technical Support Representative - Tier 2, you'll be responsible for assisting customers with technical issues that require additional troubleshooting beyond our AI-powered first-line support.

This is primarily a chat-based support role (90–95% of customer interactions), where you'll investigate technical problems, troubleshoot POS systems and retail hardware, and provide clear, timely solutions to customers.

You'll work closely with Support, Product, QA, Development, Account Management, and Customer Success teams to resolve issues and continuously improve the customer experience.

What You'll Do

• Provide technical support to customers primarily through live chat, handling issues escalated from our AI-powered support system
• Troubleshoot POS systems, retail hardware, and software-related issues, including receipt printers and other connected devices
• Investigate customer-reported problems by asking the right questions, gathering relevant information, and identifying root causes
• Guide customers through troubleshooting steps and explain technical solutions clearly and professionally
• Take ownership of customer issues, ensuring timely follow-up, accurate documentation, and appropriate escalation when needed
• Leverage internal knowledge bases, AI-powered tools, and available resources to investigate and resolve technical issues efficiently
• Collaborate with Tier 3 Support, Product, QA, and Development teams on more complex technical problems
• Maintain accurate records of customer interactions, troubleshooting steps, and resolutions
• Identify recurring issues, share customer feedback, and contribute to improvements in support processes and documentation
• Stay up to date with Sweed's platform, product updates, and evolving technical support practices

What We're Looking For

• 2+ years of experience in customer-facing support, technical support, customer service, or retail operations, preferably in a software or technology-driven environment
• Experience supporting or troubleshooting Point of Sale (POS) systems and related hardware, either remotely or hands-on
• Excellent written English communication skills, with the ability to explain technical concepts clearly and professionally through chat
• Strong verbal English communication skills
• A structured, analytical approach to troubleshooting and problem-solving
• Ability to remain calm, patient, and solution-oriented when assisting frustrated customers or handling urgent issues
• Strong attention to detail, documentation skills, and a sense of ownership and accountability
• Comfortable working with web-based software, support platforms, CRMs, and AI-powered tools
• Ability to work independently, collaborate with teammates, and escalate issues effectively
• Availability to work the required schedule, including weekends, following the initial training period

Preferred Qualifications

• Previous experience supporting SaaS platforms or complex software products
• Familiarity with retail operations, inventory management, eCommerce, or payment processing
• Experience troubleshooting retail hardware, such as receipt printers, barcode scanners, cash drawers, or scales
• Experience investigating more advanced technical issues involving APIs, integrations, or application logs
• Familiarity with tools such as Intercom, Salesforce, HubSpot, Slack, or similar support and collaboration platforms
• Experience in the cannabis retail industry or familiarity with METRC and other compliance systems
• Relevant technical certifications or an IT-related background

Work Schedule

This is a remote position supporting customers during Pacific Time business hours.

• Regular schedule: Saturday through Wednesday
• Working hours: An assigned 8-hour working shift within 6:00 AM–6:00 PM Pacific Time, plus a 1-hour unpaid lunch break
• Initial training: For approximately the first two months, you'll work Monday through Friday within the same operating hours to receive training and support

What We Offer

• Compensation in USD (B2B contract with US company, hourly pay via Hubstaff)
• 100% remote work environment
• 20 paid days off per year
• 3 paid sick days
• Medical insurance after introductory period
• Equipment reimbursement (laptops, monitors, etc.)