Senior Lead, Support

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 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. 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 to metrics you moved, such as app store ratings, review velocity, CSAT, resolution times, or retention, and explain exactly what you did to move them.

You’ve built or rebuilt a support function’s foundations before: QA, coaching cadences, escalation paths, tooling.

You’ve managed 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

The team: leadership of Merchant Support and Technical Support, including coaching, development, performance management, and hiring as we grow.

The numbers: reporting and forecasting for the support org. App store rating and review velocity are yours, as is support’s contribution to net retention.

The top merchants: the escalated moments with our largest accounts, including launches, setups, technical troubleshooting, and running the escalation meetings yourself.

The inbox: regularly and by design. Staying close to merchants is how you’ll know what to build.

The systems: our conversational quality-assurance system, built on Fin’s AI tooling and complementary to the teammate who owns Fin itself. This role consumes Fin’s signal, coaches from it, and feeds knowledge gaps back.

Who You Are

You know Shopify, its ecosystem, its support norms, and its merchants, deeply enough to earn credibility in week one.

You’ve been a player/coach before and loved it. IC work keeps you sharp rather than holding you back.

You have strong opinions about what great support looks like, formed by doing the work, and you’re excited to encode them into systems.

You’re energized by owning quality, review, and revenue-driving metrics.

You’ll Enjoy Working With Us If You

Want real ownership rather than a playbook handed to you.

See AI as the biggest leverage opportunity the support craft has ever had.

Would rather ship the workflow than write the strategy doc about it.

Like working with people who care about the merchant more than the ticket.

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 100,000+ stores that use our software.

Check out our careers page to learn more.

Why Smile?

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.

You can learn more about our culture, values, and benefits on our careers page.

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.