Technical Support Specialist

Jobspage; Southwestern Ontario; Remote; CAD 55,000 - 75,000; Full time

Benefits offered by this job

Annual salary increases

Remote work

Workspace stipend

AI tooling access

Flexible hours

Flexible vacation policy

Job summary

Freshly Commerce is seeking a proactive technical support specialist to join our small, growing team. You’ll own outcomes, communicate clearly with merchants, and resolve issues across our SaaS Shopify apps.

This fully remote role welcomes candidates in all timezones; you’ll use HelpScout, video walkthroughs, and browser debugging to keep merchants happy and inform product improvements. Join a dedicated team of six, with opportunities to grow into leadership while delivering excellent support

Qualifications

• Previous experience in technical support at a SaaS or tech company.
• Familiarity with HelpScout or other ticketing systems.
• Hands-on knowledge of front-end development (HTML, CSS, browser dev tools).
• Understanding of REST APIs and data formats like JSON or XML.
• Experience reading API documentation and troubleshooting integrations or third‑party integrations.
• Bonus experience: Shopify theme development and Liquid knowledge.

Responsibilities

• Provide email and video support to merchants and troubleshoot issues.
• Understand product under the hood and explain how things work.
• Escalate when necessary and coordinate with teammates.
• Turn merchant feedback into actionable insights for product and engineering teams.
• Maintain clear and friendly communication in async remote setting.

Skills

Customer support

Technical troubleshooting

Clear written communication

Curiosity

Team collaboration

Attention to detail

Tools

Help Scout

Chrome DevTools

REST APIs

JSON/XML

GraphQL

Job description

At Freshly Commerce we’re on a five-year mission to become the AI-powered logistics brain for commerce. Today our three Shopify apps untangle inventory, bundling, and fulfilment for brands like Sennheiser, YAMAHA, and Stanley Drinkware; tomorrow we’ll deliver intelligent automation that feels like an on-staff ops team so merchants can focus on the vision, not the busy-work.

We're a small but mighty team of 6 core members (2 support specialists), supporting over 20,000 businesses globally. Bootstrapped and profitable, we're scrappy in our approach to learn and adapt quickly, yet we take great care in the work we deliver.

If this sounds like the kind of place you'd like to work, we'd love to hear from you!

About this role

In this role, you'll have significant ownership of your work, make impactful decisions daily, and report directly to the founders. This is a full-time remote position open to candidates in all timezones.

Support is the foundation of everything we do. Our apps have consistently maintained high ratings on the Shopify App Store because our support team genuinely cares about helping merchants succeed. As one of our early support hires, you’ll get to know our products inside and out and become a go-to expert on how things work under the hood.

You’ll be joining a small but growing support team, where we all wear many hats. You’ll need strong troubleshooting instincts, a curious mind, and a willingness to get into the weeds. You should feel comfortable making judgment calls on UX or product questions, and know when something needs to be escalated.

There’s plenty of room to grow with us, including the opportunity to step into a leadership role.

What we’re looking for:

• Someone who’s comfortable diving into technical issues and can confidently support merchants over email and through clear, helpful video recordings.
• A strong track record in customer-facing roles, with a focus on delivering thoughtful, efficient support. You listen closely, ask the right questions, and know how to turn a frustrating situation into a positive experience.
• Good judgment around what needs to be escalated and what doesn’t. You’ll know when to loop in teammates and how to make that handoff seamless for the merchant.
• An eye for patterns and the ability to turn merchant feedback into actionable insights for our product and engineering teams.
• The ability to prioritize effectively. You can assess what’s urgent, what’s important, and what can wait, especially when everything feels like it needs attention.
• Comfort with change. You stay calm when the product evolves and enjoy picking up new knowledge as you go.
• A team-first mindset. You jump in to support others, document what you’ve learned, and share what’s working so we can all move faster together.
• Strong communication skills, especially in writing. You know how to keep things clear, friendly, and easy to follow, whether you’re talking to a merchant or a teammate.
• Natural troubleshooting instincts. You enjoy working on tricky issues and figuring out what’s actually going on, not just treating the symptoms.
• Great attention to detail. You care about getting the small things right, because they add up to a better experience.
• A curious mind. You’re always learning, always testing, always a few steps ahead.
• The ability to explain complex ideas in a simple way, especially for merchants who aren’t technical.

Experience:

• Previous experience in technical support at a SaaS or tech company
• Familiarity with HelpScout or other ticketing systems
• Hands‑on knowledge of front‑end development (HTML, CSS, browser dev tools)
• Working understanding of REST APIs and common data formats like JSON or XML
• Comfort with debugging using Chrome DevTools, especially for browser or front‑end issues
• Knowledge of how HTTP and DNS work
• Experience reading API documentation and troubleshooting third‑party integrations or custom app setups
• Some exposure to GraphQL APIs
• Bonus experience:
  • Shopify theme development and Liquid: Knowing how themes interact with app blocks, line item properties, and cart/checkout logic helps when diagnosing visual or UX issues on merchant stores.
  • Understanding of Shopify’s admin and storefront APIs: Familiarity with how Shopify’s APIs behave (especially in headless or custom setups) can be useful when troubleshooting sync issues, metafields, or app‑triggered updates.

Beyond technical expertise, success in this role means embodying these three core values:

1. Resourcefulness: You are relentlessly resourceful, always finding a way to achieve the highest standards of quality. You know where to look and whom to consult when faced with challenges, understanding that we always support each other.
2. Ownership: You take complete ownership and pride in your work. This means deeply understanding our merchants' problems and how new features or updates affect them.
3. Communication: You’re clear, thoughtful, and intentional in how you communicate with both merchants and teammates. You surface issues early, share relevant context, and keep things moving without needing constant follow-up. Since we work remotely and mostly async, clear communication helps us stay aligned.

Async by default

If you’ve ever ended a day of back-to-back meetings wondering when you were supposed to get any actual work done—we get it. We’ve been there. That’s why we’ve built a culture that protects time, encourages focus, and trusts you to do great work without constant check‑ins.

We meet once a week for 30 minutes on Mondays. The rest of the time, we default to async: clear Slack threads, thoughtful Looms, and shared documents.

Perks & compensation

• Competitive salary + annual pay increases
• $1,000 annual workspace stipend for laptop, headphones, or that standing desk you’ve been eyeing.
• AI tooling on us – full access to Cursor, Claude, ChatGPT, Gemini (and whatever else you need) for research and coding.
• Flexible hours – work when you’re most productive; we just ask for ~4 hours of overlap with Eastern Time (9 am to 5 pm EST).
• Flexible vacation policy – take the time you need, no arbitrary caps.

Our interview process

1. Application & short demo video: Submit your application plus the two-minute recorded screen-share. Both founders watch every submission, so take the chance to show how you think, not just what you click.
2. Conversation with the co-founders (30 min): Meet Lichen (CEO) and Basil (CTO). We’ll talk about projects you’ve worked on, how you approach support and problem‑solving, and what kind of work energizes you.
3. Paid take-home assignment: We’ll send you a real‑life merchant scenario to work through and pay you $100 USD for your time.
4. Reference chats: We’ll speak with two people you’ve worked with to understand your collaboration style and strengths.
5. Offer: If it’s a match, we move quickly, answer any final questions, and welcome you to the team.