Smile.io is the world’s largest loyalty platform, providing easy-to-use reward programs that help scaling ecommerce brands transform one-time sales into repeat purchases from loyal customers. Over 100,000 brands use Smile to turn transactional purchases into passionate repeat shoppers. We currently power over 100,000 rewards programs, reaching more than 500 million customers, and serving 1 million API requests per hour.
Smile is a remote-first company built on trust, ownership, and continuous improvement. We believe great work happens when people feel supported, challenged, and empowered to do their best work.
This is a full-time remote role working in Canada, Monday to Friday, with significant overlap with 9 AM - 3 PM EST.
🎯 About the Role
In the Shopify ecosystem, support is a growth engine. Merchants choose apps by their reviews, and reviews are earned one great support conversation at a time. The person in this role owns that engine.
We’re hiring a Sr Lead, Support to lead our Merchant Support and Technical Support teams, the escalated teams behind launches, setups, and technical troubleshooting. This is a player/coach/builder role. You’ll coach and develop the team, own the metrics that tell us whether support is working, and build the scalable systems that let a small team deliver 5-star support at growing volume: supporting Fin, and building our conversational quality-assurance system on Fin’s AI tooling. You’ll also stay in the work, because merchant conversations are a daily part of this job.
📈 The Bar
We evaluate every candidate for this role against three things. If reading them makes you lean in rather than back, keep going.
1 · Autonomy: owns the ambiguity
This role comes with real ownership. The foundational pieces of our support and escalated-support motions are yours to build.
You owncoaching, reporting, forecasting, and performance managementfor both teams, along with the decisions that come with them. You own ourapp store rating and review velocityas first-class metrics, and you run the support experience that underpins our net retention targets. Support is the front line under that number. You know when coaching is working and when it isn’t, and you make the transition to performance management deliberately rather than late. When something is broken, whether a queue, a workflow, or a knowledge gap, you fix it or build the fix, then tell us what you did.2 · Craft: elite at the execution step, with taste
Shipped improvements that move a metric matter more here than ideas about support. We want to see a track record.
You can point tometrics you moved, such as app store ratings, review velocity, CSAT, resolution times, or retention, and explain exactly what youdid to move them. You’vebuilt or rebuilt a support function’s foundationsbefore: QA, coaching cadences, escalation paths, tooling. You’vemanaged performance honestly, including the hard conversations, and your former reports would still vouch for you. Taste is part of the bar.Strong execution at Jira produces a very different support conversation than strong execution at Apple or Linear. Ours reads friendly, concise, and helpful, with no walls of text and nothing robotic.3 · Leverage: multiplies with AI
At Smile we’re strong advocates for using AI to help speed up iteration, increase productivity, and save our human brainpower for the really challenging problems. The best support leaders also have range. They’ve worked in or alongside success, product, ops, or RevOps, and they pull those muscles into support daily. One week the job needs an analyst, the next a coach, the next a systems builder, the next a person calmly running an escalation call with a top merchant.
You translate support signal into product insight, retention risk into a success play, and ticket data into a forecast finance can trust. You’ve built things yourself: AI-assisted triage, QA rubrics, workflows, reporting pipelines. You bring high taste and deep craft to support systems. You know what world-class looks like, and you build toward it in ways that scale without adding headcount linearly. Adjacent teams seek you out because you speak their language, and merchants can’t tell where support ends and the rest of the company begins.🛠 What You’ll Own
👋 Who You Are
🤝 You’ll Enjoy Working With Us If You
This probably isn’t the right fit if you’re looking for a pure people-management role where the team handles the merchant conversations.
💰 Compensation & Benefits
- Compensation: $90,000 to $100,000 CAD OTE.
- In addition, our generous total rewards package includes things like flexible vacation, a remote work allowance, and a monthly credit to use at any of the store 100,000+ stores that uses our software.
- Check out our careers page to learn more.
💛 Why Smile?
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