Technical Support Representative
Job Description
Hi there!
We're Sweed, a product-driven startup building an all-in-one cannabis retail platform.
We're looking for a Technical Support Representative 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 Us
At Sweed, we’re reimagining how cannabis retailers operate. Our enterprise-grade platform combines POS, eCommerce, Marketing, Analytics and Inventory Management into a single, seamless solution—eliminating the need for multiple third-party tools.
We believe in simplicity, efficiency, and innovation. That’s why we build for scalability and performance, making life easier for cannabis retailers while driving real business growth.
Why We’re Doing This
At Sweed, we believe in the medicinal potential of cannabis. It has been shown to help with chronic pain, anxiety, depression, and many other conditions. Despite the lingering stigma, we see cannabis as a powerful tool for improving lives.
The industry is evolving rapidly, and we’re here to drive that transformation—making cannabis retail more efficient, accessible, and customer-friendly.
Where We Are Now
We’ve been on the market for 7 years, continuously growing and refining our product.
Our focus is on earning customer trust, which means constantly improving our delivery processes and rolling out new features. At the same time, we navigate the complex legal landscape of the cannabis industry, ensuring our platform remains compliant and future-proof.
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 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.
You'll work closely with our Support, Product, QA, Development, Account Management, and Customer Success teams to resolve issues and continuously improve the customer experience.
We're looking for someone who enjoys solving technical problems, communicates clearly in writing, and takes ownership of customer issues from start to finish.
This role also offers opportunities to develop deeper technical expertise and grow into more advanced support responsibilities over time.
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
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
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 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
