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Open nowPosted 28 hours ago

Technical Support Representative

sweedpos.com13 open roles

Where
Jamaica
Work mode
Remote
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Your applicationOpen nowTechnical Support Representativesweedpos.com · Jamaica

  1. YouYes, apply to this one.

  2. CV RocketCV written for this posting.

  3. 25 readersRecruiter, hiring manager, skeptic. Round after round.

  4. CV RocketApplied on sweedpos.com's own form.

The reply lands in your private mailbox

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The clock on this job

Early applications get read.

12.8% of postings close within 7 days. Measured by our own scanner across the market. sweedpos.com postings stay open a median of 19 days.

Share of postings closed within
  1. 2.2%1 day
  2. 4.5%3 days
  3. 12.8%7 days
  4. 20.6%14 days
  5. 35.6%30 days
  6. 58.4%60 days
This job: posted 28 hours ago

sweedpos.com median: 19 days open

The posting

HI THERE!

We're Sweed https://sweedpos.com/#/, 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

1. Recruiter Interview (30 minutes): A conversation about your relevant experience, technical background, English communication skills, and expectations

2. Technical & Team Interview (30 minutes): A discussion with our Support Team Leads to explore your troubleshooting experience, technical knowledge, and approach to customer issues

3. Hiring Manager Interview (30 minutes): A conversation focused on your experience, problem-solving approach, and alignment with the team's expectations

4. Final Interview (if needed): An additional conversation with senior leadership

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    The review screen in CV Rocket: how each CV was read, round by round.

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