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
Some of the most ambitious loyalty brands on Shopify run their programs on Smile, and the relationships we build with them are one of the strongest growth levers we have. We’re hiring a Key Accounts Manager to own those relationships end to end.
You’ll be the accountable owner of net retention and top-account health across our key accounts book. You’ll carry the relationships personally, shape the motion behind them, and put a clear owner on every renewal, save, and expansion conversation.
This is a player/builder/peer-coach role:
Player. You carry the relationships yourself: business reviews, renewal conversations, save calls, and expansion conversations with the merchants who matter most. You’re in the accounts weekly.
Builder. The key-accounts motion is yours to shape: how we segment, when we engage, what a save play looks like, what triggers an expansion conversation, and how we spot risk early. You’ll help shape our 1-many success strategy too, so the whole base benefits.
Peer-coach. You’ve levelled people up before, direct reports or peers, and you’ll do it here as a supportive peer-leader who brings commercial skills and perspective to a growing team.
You’ll work closely with our Sr Lead, Support, who runs the escalated-support front line for these same merchants. They support the number from the technical side. You own it.
📈 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 of the key accounts.
You own retention outcomes and account health for our top merchants, including saves and expansion, along with the decisions that come with them: which accounts get your time, which plays get run, and when to escalate versus hold.
You build your own operating system: account plans, risk signals, engagement cadences, and save plays. You’ll have the room to design it the way you think it should work.
When a top merchant is at risk, you get on the call and run the save, then tell us what you did.
2 · Craft: Elite at the Execution step, with Taste
Renewed and expanded revenue matters more here than ideas about account management. We want to see a track record.
You can point to retention numbers you moved, such as gross retention, net retention, save rates, or expansion revenue, and explain exactly what you did to move them, account by account if we ask.
You’ve built or rebuilt an account-management motion before: segmentation, cadences, risk detection, and save plays that outlived your tenure.
You’ve run hard commercial conversations, including pricing pushback, downgrade threats, and exec-level escalations, and won more than you lost, with relationships intact either way.
You’ve coached or levelled up the people around you, direct reports or peers, and they’d say so.
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 account owners also have range. They’ve worked in or alongside success, sales, support, or product, and they pull those muscles into the book daily. One week the job needs a commercial negotiator, the next an analyst reading usage data for risk, the next a loyalty strategist, the next the person calmly holding a relationship together through a rough technical patch.
You translate merchant signal into retention risk early, product friction into a roadmap conversation, and usage data into an expansion case the merchant actually believes.
You’ve built things yourself: account-planning frameworks, risk-scoring approaches, QBR formats, save playbooks.
You raise the commercial ceiling of the team around you by sharing plays, perspectives, and reps. Peers pull you into their hardest accounts because you make them better.
You turn your best merchants into advocates through case studies, references, and app store reviews, because in the Shopify ecosystem, reviews drive ranking and ranking drives installs.
🛠 What You’ll Own
The number: net retention and the health of our top accounts, including saves, expansion, and the leading indicators underneath them. You’ll report on it, forecast it, and stand behind it.
The book: our Plus and Enterprise merchants, plus a selection of our largest Growth-segment brands.
The relationships: regular, proactive engagement with the merchants in your book. You are the merchant’s person at Smile.
The playbook: the key-accounts motion itself, including segmentation, risk signals, engagement cadences, and save and expansion plays, designed by you and documented so it’s repeatable.
The partnership with support: a tight operating rhythm with the Sr Lead, Support so escalated technical moments get resolved fast and turn into stronger relationships.
The advocacy engine: turning your strongest relationships into reviews, references, and case studies.
The team’s commercial level-up: supporting our 1-many success strategy by bringing commercial skills, perspectives, and plays to a growing team.
👋 Who You Are
You know Shopify, its ecosystem, its merchants, and how Plus and Enterprise brands actually operate, deeply enough to earn credibility in week one.
You’ve owned a revenue or retention number before and liked how it felt. Accountability reads as freedom to you.
You’ve saved accounts that other people had written off, and you can tell us exactly how.
You want to build the motion, not just run one someone else designed.
You get energy from making the people around you better. You’ve been the teammate peers pull into their hardest deals.
🤝 You’ll Enjoy Working With Us If You
Want real ownership rather than a playbook handed to you.
Think of support, product, and data as tools in your kit rather than other people's departments.
Are energized by the hard renewal conversation.
Would rather make ten teammates more commercial than be the hero on every account.
This probably isn’t the right fit if you want a book of business handed to you with the playbook already written, or if you measure your impact in meetings held rather than revenue retained.
💰 Compensation & Benefits
Compensation: $90,000 to $120,000 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.
Reports to the Head of Customer Experience
💛 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.
