[Hiring] Technical Support Representative @Sweed

Role Description

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 a primarily 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.
• Work closely with Support, Product, QA, Development, Account Management, and Customer Success teams to resolve issues and continuously improve the customer experience.
• Enjoy solving technical problems, communicate clearly in writing, and take ownership of customer issues from start to finish.
• Develop deeper technical expertise and grow into more advanced support responsibilities over time.

Qualifications

• 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.
• Experience troubleshooting technical issues involving software, hardware, or complex technology products.
• 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.

Requirements

• 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 full-time, 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 from senior team members.
• Following the training period, you'll transition to the regular Saturday–Wednesday schedule.
• Weekend availability is an essential part of this role.

Why Join Sweed?

• Work remotely as part of a collaborative, product-driven technology company.
• Make a direct impact on customers who rely on Sweed to run their businesses.
• Gain experience supporting a comprehensive retail technology platform.
• Work with modern support technologies, including AI-powered tools and knowledge resources.
• Collaborate with experienced technical teams and continue developing your troubleshooting skills.
• Grow your technical expertise with opportunities to progress into more advanced support roles.
• Be part of a team that values proactivity, critical thinking, adaptability, and customer trust.

What We Offer

• Compensation in USD (B2B contract with the US company, hourly pay tracked through Hubstaff).
• 100% remote – We’re a remote-first company, no offices needed!
• 20 paid days off per year.
• 3 paid sick days.
• Medical insurance after introductory period.
• Equipment reimbursement (laptops, monitors, etc.).

Hiring Process

• Recruiter Interview (30 minutes): A conversation about your relevant experience, technical background, English communication skills, and expectations.
• Technical & Team Interview (30 minutes): A discussion with our Support Team Leads to explore your troubleshooting experience, technical knowledge, and approach to customer issues.
• Hiring Manager Interview (30 minutes): A conversation focused on your experience, problem-solving approach, and alignment with the team's expectations.
• Final Interview (if needed): An additional conversation with senior leadership.