Technical Support Specialist

Headquarters: Waterloo, Canada URL: https://careers.freshlycommerce.com/ At Freshly Commerce, we're on a mission to build the logistics brain for commerce. Today, we help 25,000 Shopify brands simplify gnarly workflows like inventory, bundling, and order fulfillment (for even the world's largest brands like Sennheiser, Godiva, YAMAHA, and Stanley Drinkware). Tomorrow, we'll deliver intelligent automation that feels like an on-site operations team so merchants can focus on building their brand. We're a fully-remote and bootstrapped company with teammates around the world. We love what we do and love who we build for. We're a small team of 9 (3 Support specialists) who amplify each other's work by working closely together: dev with support, support with marketing, and so on. We're curious, kind, scrappy yet rigorous, and highly intentional. If this sounds like the type of team you'd like to be a part of, 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. We hire slowly and keep the bar high, so the people you work with every day will be some of the best you’ve worked with. 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. What we're looking for Somone who fixes the process while you’re fixing the ticket. 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 &