Senior Lead, Support - Smile

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.

Note: 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:

1. Autonomy: Owns the Ambiguity

• You own coaching, reporting, forecasting, and performance management for both teams, along with the decisions that come with them.
• You own our app store rating and review velocity as first-class metrics, and you run the support experience that underpins our net retention targets.
• You know when coaching is working and when it isn’t, making the transition to performance management deliberately.
• When something is broken—whether a queue, workflow, or knowledge gap—you fix it or build the fix.

2. Craft: Elite at Execution with Taste

• You can point to metrics you moved (app store ratings, review velocity, CSAT, resolution times, retention) and explain what you did.
• You’ve built or rebuilt a support function’s foundations before: QA, coaching cadences, escalation paths, tooling.
• You’ve managed performance honestly, including hard conversations.
• Strong taste in execution: writing reads friendly, concise, and helpful with no robotic walls of text.

3. Leverage: Multiplies with AI

• 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, and reporting pipelines.
• You scale without adding headcount linearly by leveraging modern support systems and AI tooling.

🛠 What You’ll Own

• The Team: Leadership of Merchant Support and Technical Support, including coaching, development, performance management, and hiring.
• The Numbers: Reporting and forecasting for the support org, app store ratings, review velocity, and net retention contribution.
• Top Merchants: Escalated moments with our largest accounts, including launches, setups, technical troubleshooting, and escalation meetings.
• The Inbox: Regularly staying close to merchants by participating directly in support conversations.
• The Systems: Conversational quality-assurance system built on Fin’s AI tooling.

👋 Who You Are

• Deeply familiar with Shopify, its ecosystem, support norms, and merchants.
• Experienced as a hands-on player/coach who loves staying sharp with IC work.
• Energized by owning quality, review, and revenue-driving metrics.

💰 Compensation & Benefits

• Compensation: $90,000 to $100,000 CAD OTE.
• Flexible vacation.
• Remote work allowance.
• Monthly credit to use at any of the 100,000+ stores using our software.