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Lead the Merchant and Technical Support teams by coaching staff, managing performance, and overseeing key support metrics. Act as a player-coach by handling escalated merchant issues and building scalable support systems using AI tools.
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.
\nIn 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.
We evaluate every candidate for this role against three things. If reading them makes you lean in rather than back, keep going.
This role comes with real ownership. The foundational pieces of our support and escalated-support motions are yours to build.
Shipped improvements that move a metric matter more here than ideas about support. We want to see a track record.
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.
This probably isn’t the right fit if you’re looking for a pure people-management role where the team handles the merchant conversations.
Our Commitment to Candidates:
At Smile, we understand that finding a new role is challenging and that self-doubt or imposter syndrome can prevent you from applying to a role, don’t let it! You have a ton to offer and we want you to feel encouraged to apply, even if you don’t check all of the boxes. If you are passionate about eCommerce and helping merchants grow through loyalty and reward, connect with us.
At Smile, we rely on a range of backgrounds, experiences, and ideas. We value diversity, and we’re proud to be an inclusive, equal opportunity workplace. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Smile welcomes and encourages applications from people with disabilities. Accommodations are available on request for candidates taking part in all aspects of the selection process.
AI Disclaimer: 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. While we’re happy for AI to help you generate or tailor your resume, we’d ask that you please refrain from using AI to answer any of the questions on this application form, or to answer questions during the interview process itself.
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