About this role.
Dutchie is seeking a full-time remote Product Support Specialist to provide frontline technical support for its dispensary technology platform. The role handles inbound email, phone, and chat contacts across POS, ecommerce, payments, loyalty, hardware, integrations, inventory, and compliance-adjacent workflows. Success requires clear customer communication, calm troubleshooting during high-urgency retail situations, accurate ticket documentation, and timely escalation to Tier 2. The specialist will use AI-assisted support tools daily and help customers adopt Dutchie’s expanding AI-native platform capabilities. Evening, weekend, and holiday availability is required within a 5am–9pm PST, seven-day support operation.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
4/5Pace & Pressure
5/5Autonomy Level
3/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
Skills and capabilities most closely associated with this opportunity.
Sample interview questions
I would first acknowledge the urgency, quickly collect the exact error, affected register, recent changes, and scope of impact, then begin targeted troubleshooting. I would communicate concise status updates and move to phone or Zoom if that would accelerate diagnosis. If meaningful progress is not made within the escalation window, I would escalate with complete notes, timestamps, troubleshooting steps, and business impact.
I start by defining the expected behavior, actual behavior, affected users, timing, and reproducibility. I review account configuration, recent changes, logs or error messages, integration status, and relevant documentation before testing the least disruptive corrective steps. I document findings clearly and escalate with evidence when the issue requires deeper technical investigation.
I prioritize contacts by urgency, customer impact, and whether an active retail operation is blocked. I use structured notes, tags, templates, and clear next steps so that no interaction loses context when I switch channels. I also set realistic expectations with customers and escalate promptly rather than allowing complex issues to stall.
I would stay calm, validate the operational impact, and avoid assigning blame before confirming the facts. I would gather the relevant transaction, bank-linking, authorization, and timing details, explain what I am checking in plain language, and provide the next action or escalation path. My goal is to give the customer confidence that their issue is owned and being actively progressed.
I use AI as a way to accelerate triage, surface relevant knowledge, and improve consistency, while verifying outputs against the customer’s actual situation and product behavior. I would flag inaccurate suggestions, missing documentation, and recurring patterns so the tool and internal processes can improve. Customer trust, data accuracy, and sound technical judgment remain essential.
About Dutchie
Founded in 2017, Dutchie is a comprehensive technology platform powering dispensary operations, while providing consumers with safe and easy access to cannabis. Dutchie aims to further support the positive societal change the cannabis industry brings to the world through wellness benefits, social justice, and empowering local communities through tax revenue. Powering thousands of dispensaries across 40+ markets throughout the United States and Canada, Dutchie is the leading technology company in the cannabis space and was named in Fast Company’s 10 Most Innovative Companies in North America and listed two years in a row on LinkedIn’s Top 50 Startups.
Dutchie has raised over $600M in funding to date, backed by D1 Capital Partners, Tiger Global, Dragoneer, DFJ Growth, Thrive Capital, Howard Schultz, Snoop Dogg’s Casa Verde Capital, Gron Ventures, members of the founding team at DoorDash, Kevin Durant’s Thirty Five Ventures, and other notable angel investors.
About This Job
Dutchie is on a mission to make cannabis accessible — and we do that by building the technology that powers dispensaries end-to-end: point of sale, ecommerce, payments, loyalty, and marketing. Our Support team sits at the center of that mission. When something isn’t working for a dispensary, we’re the ones who make it right; fast, sharp, and calm.
The Product Support Specialist is our frontline expert across the full Dutchie platform. You’ll own inbound contacts for our full stack of products, troubleshoot technically complex issues, navigate multiple systems, and be the person dispensary staff rely on when things get hard in the middle of a busy shift. Many of the analysts, engineers, implementation strategists, operations specialists, and more started in this exact position or very similar, meaning this can be a launchpad for future career growth.
One more thing worth being direct about: Dutchie is actively building AI into how cannabis retail operates. We utilize AI-powered support products, and we’re rolling out agentic modules across the platform that change how dispensaries interact with their technology. AI isn’t a tool we use on the side, it’s woven into the product you’ll be supporting and the workflow you’ll operate in every day. We’re looking for someone genuinely curious about these tools, invested in learning them, and willing to push on them when they fall short. If you’ve been waiting for a support role where the technology is actually interesting, this is it.
What You’ll Do
Customer interaction and resolution
- Handle inbound contacts via email, phone, and live chat across POS, ecommerce, payments, loyalty, hardware, and integrations
- Troubleshoot complex platform issues: back office configuration, register transactions, receipt reconciliation, menu sync failures, discount and pricing issues
- Support hardware setup and troubleshooting across registers, printers, barcode scanners, cash drawers, scales, and computers
- De-escalate high-urgency situations, dispensary customers are often mid-shift, and the stakes are real
- Know when to escalate to a higher level or move to a call or Zoom rather than continuing to trade messages
Payments and compliance
- Triage Pay by Bank issues: bank linking, funding delays, authorization errors, returns, and suspected fraud
- Support basic METRC and compliance workflows: package tags, manifest generation, transfer workflows
- Escalate compliance-adjacent issues to Tier 2 with complete documentation
Inventory, products, and integrations
- Assist with inventory receiving, package creation, inventory room management, and audit workflows
- Support catalog management, label configuration, and pricing updates
- Validate integration setup, triage syncing issues, and process API key requests
AI tool usage and platform evolution
- Work alongside AI-assisted support tooling as a daily part of how you triage, troubleshoot, and route issues — not as a workaround, but as the workflow
- Support customers using Dutchie’s AI-native products and agentic platform modules that are actively expanding
- Bring genuine curiosity: experiment with new tools as they roll out, flag gaps when you find them, and contribute to how the tooling improves
- Contribute to internal documentation when you resolve something that wasn’t written down. Every gap you close makes the whole team faster
Documentation and escalation
- Write complete ticket documentation on every contact: issue reported, steps taken, outcome, and next steps
- Apply the 20-minute rule: if meaningful progress toward resolution hasn’t been made, escalate with full context
- Apply correct classifications, tags, and macros before closing or escalating
What you Bring
- 2+ years in a customer-facing support role, preferably supporting a SaaS platform
- Strong written and verbal communication skills, you can explain a technical issue in plain language
- Comfort troubleshooting across multiple product surfaces simultaneously
- Strong documentation habits: your internal notes are actionable without follow-up
- Professional composure with frustrated customers in high-urgency situations
- Comfort working in web-based software, CRMs, and Google Workspace
- Genuine appetite for AI tooling, you’re curious about how these tools work, willing to push on them, and energized rather than anxious when the technology around you is evolving fast
- Flexibility to work evenings, weekends, and holidays. This is a 7-day operation (5am–9pm PST)
It’s a Bonus if You Have…
- Experience with POS systems, retail operations technology, or cannabis compliance
- Familiarity with Zendesk, Salesforce, Slack, and Zoom
- Background in the cannabis industry or dispensary operations
- Experience with the Dutchie platform
Schedule
Full-time, remote. Hours of operation are 5am–9pm PST, 7 days a week. Availability for evenings, weekends, and holidays is required – schedules are set through a vacation bid process that gives you structure and predictability while keeping the team covered.
What you’ll get
The hourly rate is $24.04 based on the intended level.
In addition to cash compensation, our total rewards package includes:
- Medical benefits including dental and vision plans to ensure you always have the best care.
- Equity packages in the form of stock options to all employees.
- Technology (hardware, software, reading materials, etc..) allowance
- Flexible vacation and sick days
At Dutchie, we’re committed to providing an environment of mutual respect where equal employment opportunities are available to all applicants and teammates without regard to race, color, religion, sex, sexual orientation, gender identity or expression, pregnancy, age, national origin, disability status, genetic information, protected veteran status, or any other characteristic protected by law. Dutchie believes that diversity and inclusion among our teammates is critical to our success, and we seek to recruit, develop and retain the most talented people from a diverse candidate pool.
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